Unnamed: 0
int64 0
445k
| level_0
int64 0
1.94M
| index
float64 0
1.81M
⌀ | original_rxn
stringlengths 104
2.67k
| fragments
stringlengths 6
161
⌀ | source
stringlengths 11
26
| year
int64 1.98k
2.02k
| mapped_rxn
stringlengths 110
2.63k
| confidence
float64 0
1
| canonical_rxn_with_fragment_info
stringlengths 25
599
| canonical_rxn
stringlengths 25
599
| ID
stringlengths 17
32
| reaction_hash
stringlengths 56
56
| reactants
stringlengths 55
1.33k
| products
stringlengths 51
1.3k
| retro_template
stringlengths 46
417
| template_hash
stringclasses 1k
values | selectivity
float64 0
1
| outcomes
float64 1
15
| reagents
stringlengths 1
370
⌀ | labels
int64 0
999
|
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
354,083 | 533,275 | null | [CH:1]1([NH2:4])[CH2:3][CH2:2]1.[OH:5][C:6]1[CH:11]=[C:10]([OH:12])[N:9]=[C:8](SC)[N:7]=1>CO>[CH:1]1([NH:4][C:8]2[N:9]=[C:10]([OH:12])[CH:11]=[C:6]([OH:5])[N:7]=2)[CH2:3][CH2:2]1 | null | US20080004271A1_0857 | 2,008 | CO.CS[c:7]1[n:6][c:4]([OH:5])[cH:3][c:2]([OH:1])[n:12]1.[NH2:8][CH:9]1[CH2:10][CH2:11]1>>[OH:1][c:2]1[cH:3][c:4]([OH:5])[n:6][c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[n:12]1 | 0.510979 | CO.CSc1nc(O)cc(O)n1.NC1CC1>>Oc1cc(O)nc(NC2CC2)n1 | CO.CSc1nc(O)cc(O)n1.NC1CC1>>Oc1cc(O)nc(NC2CC2)n1 | US20080004271A1_0857apps | a1107ac67c38ca3d27deef4cc88456aa25a8a41867b05713fb4e51e2 | CO.CS[c:7]1[n:6][c:4]([OH:5])[cH:3][c:2]([OH:1])[n:12]1.[NH2:8][CH:9]1[CH2:10][CH2:11]1 | [OH:1][c:2]1[cH:3][c:4]([OH:5])[n:6][c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[n:12]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[NH;D2;+0:5]-[C:4])>>(C-S-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C:4]-[NH2;D1;+0:5]) | 937b5277d1ff8687ad859fd8f0d7d8167675c967e486257067c90da5 | 1 | 1 | CO | 101 |
147,633 | 528,733 | 886,171 | [CH3:1][NH:2][C:3](=[O:14])[CH2:4][CH2:5][CH:6]([N+:11]([O-])=O)[CH:7]([OH:10])[CH2:8][F:9]>CO.[Ni]>[CH3:1][NH:2][C:3](=[O:14])[CH2:4][CH2:5][CH:6]([NH2:11])[CH:7]([OH:10])[CH2:8][F:9] | null | US07504382B2_0173 | 2,009 | CO.O=[N+:8]([O-])[CH:7]([CH2:6][CH2:5][C:3]([NH:2][CH3:1])=[O:4])[CH:9]([OH:10])[CH2:11][F:12].[Ni]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][CH2:6][CH:7]([NH2:8])[CH:9]([OH:10])[CH2:11][F:12] | 0.998578 | CNC(=O)CCC(C(O)CF)[N+](=O)[O-].CO.[Ni]>>CNC(=O)CCC(N)C(O)CF | CNC(=O)CCC(C(O)CF)[N+](=O)[O-].CO.[Ni]>>CNC(=O)CCC(N)C(O)CF | US07504382B2_0173grants | 74bc7abade2c0eb885b6d29ba82904f3cebba6a3253dff7c012783d4 | CO.O=[N+:8]([O-])[CH:7]([CH2:6][CH2:5][C:3]([NH:2][CH3:1])=[O:4])[CH:9]([OH:10])[CH2:11][F:12].[Ni] | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][CH2:6][CH:7]([NH2:8])[CH:9]([OH:10])[CH2:11][F:12] | ([C:2]-[NH2;D1;+0:1])>>(O=[N+;H0;D3:1](-[C:2])-[O-]) | 3c04bb94cdc004d27a70f3e0095c88d7e55a882e6808ba41937bbfde | 1 | 1 | CO.[Ni] | 226 |
126,950 | 466,798 | 790,831 | [CH:1]([O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[CH:13])=[CH:8][C:7]=1[CH2:14][N:15]([CH:17]1[CH2:19][CH2:18]1)[CH3:16])([CH3:3])[CH3:2].[CH3:21][O:22][C:23](=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=1.C(N(CC)CC)C.C(OCC)(=O)C>CCCCCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]([O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:28]2[CH:29]=[CH:30][C:25]([CH2:24][C:23]([O:22][CH3:21])=[O:32])=[CH:26][CH:27]=2)=[CH:8][C:7]=1[CH2:14][N:15]([CH:17]1[CH2:19][CH2:18]1)[CH3:16])([CH3:3])[CH3:2] | |^1:56,75| | US07226951B2_0713 | 2,007 | CCCCCC.CCN(CC)CC.CCOC(C)=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.I[c:9]1[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:31][cH:30]1.[CH:10]#[C:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])[c:22]([CH2:23][N:24]([CH3:25])[CH:26]2[CH2:27][CH2:28]2)[cH:29]1.[Cu]I>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])[c:22]([CH2:23][N:24]([CH3:25])[CH:26]3[CH2:27][CH2:28]3)[cH:29]2)[cH:30][cH:31]1 | 0.626463 | C#Cc1ccc(C(=O)OC(C)C)c(CN(C)C2CC2)c1.CCCCCC.CCN(CC)CC.CCOC(C)=O.COC(=O)Cc1ccc(I)cc1.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>>COC(=O)Cc1ccc(C#Cc2ccc(C(=O)OC(C)C)c(CN(C)C3CC3)c2)cc1 | C#Cc1ccc(C(=O)OC(C)C)c(CN(C)C2CC2)c1.CCCCCC.CCN(CC)CC.CCOC(C)=O.COC(=O)Cc1ccc(I)cc1.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>>COC(=O)Cc1ccc(C#Cc2ccc(C(=O)OC(C)C)c(CN(C)C3CC3)c2)cc1 | US07226951B2_0713grants | ed88df863a82743be17603df92cf3c9a1bc27e88619358fcbc1e5f7a | CCCCCC.CCN(CC)CC.CCOC(C)=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.I[c:9]1[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:31][cH:30]1.[CH:10]#[C:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])[c:22]([CH2:23][N:24]([CH3:25])[CH:26]2[CH2:27][CH2:28]2)[cH:29]1.[Cu]I | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])[c:22]([CH2:23][N:24]([CH3:25])[CH:26]3[CH2:27][CH2:28]3)[cH:29]2)[cH:30][cH:31]1 | ([C:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(I-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]#[CH;D1;+0:5]) | 342ec13d6dc46f8caedd04911cf98542ef6704fb7da33fd6b60ef2c6 | 0.5 | 2 | CCCCCC.CCN(CC)CC.CCOC(C)=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I | 664 |
241,456 | 804,384 | 1,331,895 | C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]#[N:15])[CH2:9]1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]#[N:15])[CH2:9]1 | |f:1.2| | US08461328B2_1479 | 2,013 | CC(C)(C)OC(=O)[NH:8][CH:7]1[CH2:6][CH2:5][CH2:4][CH:3]([C:2]#[N:1])[CH2:9]1.ClCCl.O=C(O)C(F)(F)F>>[N:1]#[C:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([NH2:8])[CH2:9]1 | 0.998121 | CC(C)(C)OC(=O)NC1CCCC(C#N)C1.ClCCl~O=C(O)C(F)(F)F>>N#CC1CCCC(N)C1 | CC(C)(C)OC(=O)NC1CCCC(C#N)C1.ClCCl.O=C(O)C(F)(F)F>>N#CC1CCCC(N)C1 | US08461328B2_1479grants | 1d3bea5ddd439a7ce405e851fb75c52d3f70fb0c3145ddf59cabbead | CC(C)(C)OC(=O)[NH:8][CH:7]1[CH2:6][CH2:5][CH2:4][CH:3]([C:2]#[N:1])[CH2:9]1.ClCCl.O=C(O)C(F)(F)F | [N:1]#[C:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([NH2:8])[CH2:9]1 | ([C:2]-[NH2;D1;+0:1])>>(C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]) | 6c83f45f485301792011c63e6835be21ece3be24f5b32a6e45acc5be | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 538 |
394,790 | 1,249,576 | null | [OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][CH:17]=[CH:16]4)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:22][CH3:23].[N:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32]O)=[CH:26][CH:25]=1>>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][C:6]3[C:5]4[C:10](=[CH:11][C:2]([O:1][CH2:32][CH2:31][O:30][C:27]5[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=5)=[C:3]([O:22][CH3:23])[CH:4]=4)[N:9]=[CH:8][N:7]=3)=[CH:21][CH:20]=2)[CH:16]=[CH:17]1 | null | US20120197027A1_0871 | 2,012 | O[CH2:24][CH2:25][O:26][c:27]1[cH:28][cH:29][n:30][cH:31][cH:32]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][CH2:25][O:26][c:27]1[cH:28][cH:29][n:30][cH:31][cH:32]1 | 0.954069 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.OCCOc1ccncc1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCOc1ccncc1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.OCCOc1ccncc1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCOc1ccncc1 | US20120197027A1_0871apps | 245db63b344169a30173e3a25063549652c6ef43b4998987ff002f84 | O[CH2:24][CH2:25][O:26][c:27]1[cH:28][cH:29][n:30][cH:31][cH:32]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23] | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][CH2:25][O:26][c:27]1[cH:28][cH:29][n:30][cH:31][cH:32]1 | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(O-[CH2;D2;+0:1]-[C:2]).([OH;D1;+0:3]-[c:4]) | 6b5437625f42979eb76da5582165cd62b5dfeb41d76ac0fbed0bf4a3 | 0.5 | 2 | null | 478 |
16,186 | 79,938 | 130,670 | [CH3:1][NH:2][C:3](=[O:32])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@H:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[NH:8][C@@H:9]([C:14]([O:16]C)=[O:15])[CH2:10][CH2:11][S:12][CH3:13].O.CC(O)=O>CO.[OH-].[Na+]>[CH3:1][NH:2][C:3](=[O:32])[C@H:4]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[NH:5][C:6](=[O:22])[C@H:7]([CH2:18][CH:19]([CH3:20])[CH3:21])[NH:8][C@@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][S:12][CH3:13] | |f:4.5| | US04511504_ | 1,985 | CC(=O)O.CO.C[O:31][C:29]([C@H:24]([NH:23][C@H:18]([C:16]([NH:15][C@H:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1)=[O:17])[CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:25][CH2:26][S:27][CH3:28])=[O:30].O.[Na+].[OH-]>>[CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1)[NH:15][C:16](=[O:17])[C@H:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[NH:23][C@H:24]([CH2:25][CH2:26][S:27][CH3:28])[C:29](=[O:30])[OH:31] | 0.660503 | CC(=O)O.CNC(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)[C@H](CC(C)C)N[C@H](CCSC)C(=O)OC.CO.O.[Na+]~[OH-]>>CNC(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)[C@H](CC(C)C)N[C@H](CCSC)C(=O)O | CC(=O)O.CNC(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)[C@H](CC(C)C)N[C@H](CCSC)C(=O)OC.CO.O.[Na+].[OH-]>>CNC(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)[C@H](CC(C)C)N[C@H](CCSC)C(=O)O | US04511504_grants | 8950da16d1827f09c93107bb333cae8f2d02e8a0f8ad48f817e20cfb | CC(=O)O.CO.C[O:31][C:29]([C@H:24]([NH:23][C@H:18]([C:16]([NH:15][C@H:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1)=[O:17])[CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:25][CH2:26][S:27][CH3:28])=[O:30].O.[Na+].[OH-] | [CH3:1][NH:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1)[NH:15][C:16](=[O:17])[C@H:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[NH:23][C@H:24]([CH2:25][CH2:26][S:27][CH3:28])[C:29](=[O:30])[OH:31] | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | CC(=O)O.CO.O.[Na+].[OH-] | 88 |
339,773 | 294,219 | null | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:34]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:34][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([CH:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])=[CH:6][CH:7]=1 | null | US20050239780A1_0161 | 2,005 | CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl.O=C1CCC(=O)N1[Br:14].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@H:8]([c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:15][cH:16]1)[CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@H:8]([c:9]1[cH:10][cH:11][c:12]([CH2:13][Br:14])[cH:15][cH:16]1)[CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1 | 0.398181 | CC(C)(C#N)N=NC(C)(C)C#N.Cc1ccc([C@@H](C(=O)OC(C)(C)C)C2CCOCC2)cc1.ClC(Cl)(Cl)Cl.O=C1CCC(=O)N1Br>>CC(C)(C)OC(=O)[C@H](c1ccc(CBr)cc1)C1CCOCC1 | CC(C)(C#N)N=NC(C)(C)C#N.Cc1ccc([C@@H](C(=O)OC(C)(C)C)C2CCOCC2)cc1.ClC(Cl)(Cl)Cl.O=C1CCC(=O)N1Br>>CC(C)(C)OC(=O)[C@H](c1ccc(CBr)cc1)C1CCOCC1 | US20050239780A1_0161apps | 93155a45e169c8b9b50b7191021ca487a9409f03434e3a567b449d93 | CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl.O=C1CCC(=O)N1[Br:14].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@H:8]([c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:15][cH:16]1)[CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@H:8]([c:9]1[cH:10][cH:11][c:12]([CH2:13][Br:14])[cH:15][cH:16]1)[CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1 | ([Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3])>>(O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1]).([CH3;D1;+0:2]-[c:3]) | eece798354409c857729b8ffcb1d9784ebdca6b0d62c935232f02dc9 | 1 | 1 | CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl | 29 |
407,754 | 1,578,056 | null | [CH3:1][C:2]1[C:6]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]2)=[C:5]([CH3:19])[O:4][N:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[NH2:28])=[C:23]([CH3:35])[CH:22]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:28][C:16](=[O:18])[CH2:15][N:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:19])[CH2:14][CH2:13]2)=[C:23]([CH3:35])[CH:22]=1 | null | US20140256740A1_0475 | 2,014 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCCl.O.O[C:11](=[O:12])[CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]2[c:21]([CH3:22])[n:23][o:24][c:25]2[CH3:26])[CH2:27][CH2:28]1.On1nnc2ccccc21.[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[CH:9]([NH2:10])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[CH:9]([NH:10][C:11](=[O:12])[CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]2[c:21]([CH3:22])[n:23][o:24][c:25]2[CH3:26])[CH2:27][CH2:28]1)[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1 | 0.834157 | CCN(C(C)C)C(C)C.CN(C)C=O.Cc1cc(Cl)ccc1C(N)c1ccccc1.Cc1noc(C)c1CCN1CCN(CC(=O)O)CC1.ClCCCl.O.On1nnc2ccccc21>>Cc1cc(Cl)ccc1C(NC(=O)CN1CCN(CCc2c(C)noc2C)CC1)c1ccccc1 | CCN(C(C)C)C(C)C.CN(C)C=O.Cc1cc(Cl)ccc1C(N)c1ccccc1.Cc1noc(C)c1CCN1CCN(CC(=O)O)CC1.ClCCCl.O.On1nnc2ccccc21>>Cc1cc(Cl)ccc1C(NC(=O)CN1CCN(CCc2c(C)noc2C)CC1)c1ccccc1 | US20140256740A1_0475apps | 722f2a8f1e5f4cabbb67fa4581f8642245fe472c3adac2f2e38ede71 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCCl.O.O[C:11](=[O:12])[CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]2[c:21]([CH3:22])[n:23][o:24][c:25]2[CH3:26])[CH2:27][CH2:28]1.On1nnc2ccccc21.[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[CH:9]([NH2:10])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1 | [CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[CH:9]([NH:10][C:11](=[O:12])[CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]2[c:21]([CH3:22])[n:23][o:24][c:25]2[CH3:26])[CH2:27][CH2:28]1)[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5](-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)-[c:12]1:[c:13]:[c:14]:[c:15]:[c:16]:[c:17]:1)>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[C:5](-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)-[c:12]1:[c:13]:[c:14]:[c:15]:[c:16]:[c:17]:1) | a7de99e9470b4eb4268b92ce4627e5b055b5d25de5ec99d8ddb9f3dc | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCCl.O.On1nnc2ccccc21 | 769 |
282,310 | 924,687 | 1,548,303 | [CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([F:16])[C:13](B(O)O)=[C:12]([F:20])[CH:11]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].Br[C:22]1[S:23][C:24]([CH:27]=[CH2:28])=[CH:25][CH:26]=1>>[F:20][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)[CH:15]=[C:14]([F:16])[C:13]=1[C:22]1[S:23][C:24]([CH:27]=[CH2:28])=[CH:25][CH:26]=1 | null | US08906261B2_0310 | 2,014 | Br[c:6]1[cH:5][cH:4][c:3]([CH:2]=[CH2:1])[s:24]1.OB(O)[c:7]1[c:8]([F:9])[cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([CH2:16][CH2:17][CH3:18])[cH:19][cH:20]2)[cH:21][c:22]1[F:23]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([CH2:16][CH2:17][CH3:18])[cH:19][cH:20]3)[cH:21][c:22]2[F:23])[s:24]1 | 0.618521 | C=Cc1ccc(Br)s1.CCCc1ccc(-c2cc(F)c(B(O)O)c(F)c2)cc1>>C=Cc1ccc(-c2c(F)cc(-c3ccc(CCC)cc3)cc2F)s1 | C=Cc1ccc(Br)s1.CCCc1ccc(-c2cc(F)c(B(O)O)c(F)c2)cc1>>C=Cc1ccc(-c2c(F)cc(-c3ccc(CCC)cc3)cc2F)s1 | US08906261B2_0310grants | 15adef7ad520f7296228566c8440edce78f4a060607aed55c06e5ceb | Br[c:6]1[cH:5][cH:4][c:3]([CH:2]=[CH2:1])[s:24]1.OB(O)[c:7]1[c:8]([F:9])[cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([CH2:16][CH2:17][CH3:18])[cH:19][cH:20]2)[cH:21][c:22]1[F:23] | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([CH2:16][CH2:17][CH3:18])[cH:19][cH:20]3)[cH:21][c:22]2[F:23])[s:24]1 | ([#16;a:2]:[c;H0;D3;+0:1](:[c:3])-[c;H0;D3;+0:4](:[c:5]):[c:6])>>(Br-[c;H0;D3;+0:1](:[#16;a:2]):[c:3]).(O-B(-O)-[c;H0;D3;+0:4](:[c:5]):[c:6]) | 7cc71b72b8e9c3b81fdfcd65c8ee456ae47e7ef7ebcf4175cc08dd83 | 1 | 1 | null | 864 |
248,473 | 825,182 | 1,367,193 | [NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:10]([CH3:18])[N:9]=2)[CH2:4][C@H:3]1[O:19][CH3:20].[Cl:21][C:22]1[N:23]=[C:24]([C:29](O)=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Cl:21][C:22]1[N:23]=[C:24]([C:29]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:10]([CH3:18])[N:9]=3)[CH2:4][C@H:3]2[O:19][CH3:20])=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28] | |f:2.3| | US08536197B2_1730 | 2,013 | CCN=C=NCCCN(C)C.Cl.O[C:6]([c:5]1[nH:4][c:3]([CH2:2][CH3:1])[c:29]([Cl:30])[n:28]1)=[O:7].On1nnc2ccccc21.[NH2:8][C@H:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][c:15]([C:16](=[O:17])[O:18][CH3:19])[cH:20][c:21]([CH3:22])[n:23]2)[CH2:24][C@H:25]1[O:26][CH3:27]>>[CH3:1][CH2:2][c:3]1[nH:4][c:5]([C:6](=[O:7])[NH:8][C@H:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][c:15]([C:16](=[O:17])[O:18][CH3:19])[cH:20][c:21]([CH3:22])[n:23]3)[CH2:24][C@H:25]2[O:26][CH3:27])[n:28][c:29]1[Cl:30] | 0.961255 | CCN=C=NCCCN(C)C~Cl.CCc1[nH]c(C(=O)O)nc1Cl.COC(=O)c1cc(C)nc(N2CC[C@H](N)[C@H](OC)C2)c1.On1nnc2ccccc21>>CCc1[nH]c(C(=O)N[C@H]2CCN(c3cc(C(=O)OC)cc(C)n3)C[C@H]2OC)nc1Cl | CCN=C=NCCCN(C)C.CCc1[nH]c(C(=O)O)nc1Cl.COC(=O)c1cc(C)nc(N2CC[C@H](N)[C@H](OC)C2)c1.Cl.On1nnc2ccccc21>>CCc1[nH]c(C(=O)N[C@H]2CCN(c3cc(C(=O)OC)cc(C)n3)C[C@H]2OC)nc1Cl | US08536197B2_1730grants | 3c37a0f04d44cae7824af2ef6f9987d2cfc0709c4ce882f1fb56e9f9 | CCN=C=NCCCN(C)C.Cl.O[C:6]([c:5]1[nH:4][c:3]([CH2:2][CH3:1])[c:29]([Cl:30])[n:28]1)=[O:7].On1nnc2ccccc21.[NH2:8][C@H:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][c:15]([C:16](=[O:17])[O:18][CH3:19])[cH:20][c:21]([CH3:22])[n:23]2)[CH2:24][C@H:25]1[O:26][CH3:27] | [CH3:1][CH2:2][c:3]1[nH:4][c:5]([C:6](=[O:7])[NH:8][C@H:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][c:15]([C:16](=[O:17])[O:18][CH3:19])[cH:20][c:21]([CH3:22])[n:23]3)[CH2:24][C@H:25]2[O:26][CH3:27])[n:28][c:29]1[Cl:30] | ([#7;a:4]:[c:3](:[#7;a:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[#7;a:4]):[#7;a:5]).([C:6]-[NH2;D1;+0:7]) | 0e5e4170fc9f555d7a7029bb152edf6a824a8c67b107fbdb1d9e5368 | 1 | 1 | CCN=C=NCCCN(C)C.Cl.On1nnc2ccccc21 | 951 |
340,780 | 318,528 | null | C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1)C.[NH2:14][NH2:15]>C(O)C>[CH3:12][N:9]1[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([NH:14][NH2:15])=[O:3])[CH2:7][CH2:8]1 | null | US20060004043A1_0508 | 2,006 | CCO.CCO[C:7]([CH2:6][CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:12][CH2:11]1)=[O:8].[NH2:9][NH2:10]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][C:7](=[O:8])[NH:9][NH2:10])[CH2:11][CH2:12]1 | 0.692637 | CCO.CCOC(=O)CC1CCN(C)CC1.NN>>CN1CCC(CC(=O)NN)CC1 | CCO.CCOC(=O)CC1CCN(C)CC1.NN>>CN1CCC(CC(=O)NN)CC1 | US20060004043A1_0508apps | 5ecf585963cf25c462182889d0bf233567235538336cb6656951e8a8 | CCO.CCO[C:7]([CH2:6][CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:12][CH2:11]1)=[O:8].[NH2:9][NH2:10] | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][C:7](=[O:8])[NH:9][NH2:10])[CH2:11][CH2:12]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:5]-[N;D1;H2:4])>>(C-C-O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([N;D1;H2:4]-[NH2;D1;+0:5]) | c0699a77fafc46c8c9b052a148873c5b25b385e0a4464ef373f999c1 | 1 | 1 | CCO | 164 |
415,034 | 1,707,687 | null | Br[C:2]1[C:3]([F:19])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:18]=1.[C:20]([C:22]1([OH:29])[CH2:26][CH2:25][N:24]([CH3:27])[C:23]1=[O:28])#[CH:21]>>[F:19][C:3]1[C:2]([C:21]#[C:20][C:22]2([OH:29])[CH2:26][CH2:25][N:24]([CH3:27])[C:23]2=[O:28])=[CH:18][C:6]2[C:7]3[N:8]([CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1 | null | US20150166569A1_0814 | 2,015 | Br[c:9]1[cH:10][c:11]2[c:12]([cH:13][c:14]1[F:15])[O:16][CH2:17][CH2:18][n:19]1[cH:20][c:21]([C:22]([NH2:23])=[O:24])[n:25][c:26]1-2.[CH3:1][N:2]1[CH2:3][CH2:4][C:5]([OH:6])([C:7]#[CH:8])[C:27]1=[O:28]>>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]([OH:6])([C:7]#[C:8][c:9]2[cH:10][c:11]3[c:12]([cH:13][c:14]2[F:15])[O:16][CH2:17][CH2:18][n:19]2[cH:20][c:21]([C:22]([NH2:23])=[O:24])[n:25][c:26]2-3)[C:27]1=[O:28] | 0.979822 | C#CC1(O)CCN(C)C1=O.NC(=O)c1cn2c(n1)-c1cc(Br)c(F)cc1OCC2>>CN1CCC(O)(C#Cc2cc3c(cc2F)OCCn2cc(C(N)=O)nc2-3)C1=O | C#CC1(O)CCN(C)C1=O.NC(=O)c1cn2c(n1)-c1cc(Br)c(F)cc1OCC2>>CN1CCC(O)(C#Cc2cc3c(cc2F)OCCn2cc(C(N)=O)nc2-3)C1=O | US20150166569A1_0814apps | 8dcc2ad67d2f2a2fd69323b797ebc45c26956c3b5aeab11c78286a9b | Br[c:9]1[cH:10][c:11]2[c:12]([cH:13][c:14]1[F:15])[O:16][CH2:17][CH2:18][n:19]1[cH:20][c:21]([C:22]([NH2:23])=[O:24])[n:25][c:26]1-2.[CH3:1][N:2]1[CH2:3][CH2:4][C:5]([OH:6])([C:7]#[CH:8])[C:27]1=[O:28] | [CH3:1][N:2]1[CH2:3][CH2:4][C:5]([OH:6])([C:7]#[C:8][c:9]2[cH:10][c:11]3[c:12]([cH:13][c:14]2[F:15])[O:16][CH2:17][CH2:18][n:19]2[cH:20][c:21]([C:22]([NH2:23])=[O:24])[n:25][c:26]2-3)[C:27]1=[O:28] | ([C:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]#[CH;D1;+0:5]) | 42f697fc7ae70923f5806984441d2582468344af75caeb7e213f1b10 | 1 | 1 | null | 659 |
17,646 | 86,158 | 140,556 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16](O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O.[OH-].[Na+]>>[Cl:21][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:17]=1 | |f:2.3| | US04560692_ | 1,985 | O=P(Cl)(Cl)[Cl:9].O[c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:18][cH:17]2)[n:16][c:15]2[c:10]1[cH:11][cH:12][cH:13][cH:14]2.[Na+].[OH-]>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([Cl:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1 | 0.347197 | O=P(Cl)(Cl)Cl.Oc1cc(-c2ccc(Cl)cc2)nc2ccccc12.[Na+]~[OH-]>>Clc1ccc(-c2cc(Cl)c3ccccc3n2)cc1 | O=P(Cl)(Cl)Cl.Oc1cc(-c2ccc(Cl)cc2)nc2ccccc12.[Na+].[OH-]>>Clc1ccc(-c2cc(Cl)c3ccccc3n2)cc1 | US04560692_grants | eeb25b002401ad4516f074cc32896d1c54bba857942b2b08b9a2c5de | O=P(Cl)(Cl)[Cl:9].O[c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:18][cH:17]2)[n:16][c:15]2[c:10]1[cH:11][cH:12][cH:13][cH:14]2.[Na+].[OH-] | [Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([Cl:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1 | ([Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1)>>(Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1]).(O-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1) | 07a69d7bef62cad2d8eadc2c433a5a820ab0d8e598c7eeab3c38d54e | 1 | 1 | [Na+].[OH-] | 177 |
20,696 | 99,597 | 161,466 | [CH3:1][O:2][C:3](=[O:24])[CH2:4][N:5]([CH:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:25][C:26]1([CH3:35])[CH2:31]C(O)[CH2:29][C:28]([CH3:34])([CH3:33])[NH:27]1.CC(C)([O-])C.[K+].CO>CCCCCCC>[CH3:25][C:26]1([CH3:35])[CH2:31][CH:1]([O:2][C:3](=[O:24])[CH2:4][N:5]([CH:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:29][C:28]([CH3:34])([CH3:33])[NH:27]1 | |f:2.3| | US04670488_ | 1,987 | CC(C)(C)[O-].CCCCCCC.CO.CO[C:11]([CH2:10][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH:24]1[CH2:25][C:26]([CH3:27])([CH3:28])[NH:29][C:30]([CH3:31])([CH3:32])[CH2:33]1)=[O:12].[K+].[OH:13][CH:14]1[CH2:15][C:16]([CH3:17])([CH3:18])[NH:19][C:20]([CH3:21])([CH3:22])[CH2:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][C:11](=[O:12])[O:13][CH:14]1[CH2:15][C:16]([CH3:17])([CH3:18])[NH:19][C:20]([CH3:21])([CH3:22])[CH2:23]1)[CH:24]1[CH2:25][C:26]([CH3:27])([CH3:28])[NH:29][C:30]([CH3:31])([CH3:32])[CH2:33]1 | 0.187371 | CC(C)(C)[O-]~[K+].CC1(C)CC(O)CC(C)(C)N1.CCCCCCC.CCCCCCCCN(CC(=O)OC)C1CC(C)(C)NC(C)(C)C1.CO>>CCCCCCCCN(CC(=O)OC1CC(C)(C)NC(C)(C)C1)C1CC(C)(C)NC(C)(C)C1 | CC(C)(C)[O-].CC1(C)CC(O)CC(C)(C)N1.CCCCCCC.CCCCCCCCN(CC(=O)OC)C1CC(C)(C)NC(C)(C)C1.CO.[K+]>>CCCCCCCCN(CC(=O)OC1CC(C)(C)NC(C)(C)C1)C1CC(C)(C)NC(C)(C)C1 | US04670488_grants | e9d45c0b2dabd83f4ae436ed7031013f7db1d4ae6e6520160b21daa0 | CC(C)(C)[O-].CCCCCCC.CO.CO[C:11]([CH2:10][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH:24]1[CH2:25][C:26]([CH3:27])([CH3:28])[NH:29][C:30]([CH3:31])([CH3:32])[CH2:33]1)=[O:12].[K+].[OH:13][CH:14]1[CH2:15][C:16]([CH3:17])([CH3:18])[NH:19][C:20]([CH3:21])([CH3:22])[CH2:23]1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][C:11](=[O:12])[O:13][CH:14]1[CH2:15][C:16]([CH3:17])([CH3:18])[NH:19][C:20]([CH3:21])([CH3:22])[CH2:23]1)[CH:24]1[CH2:25][C:26]([CH3:27])([CH3:28])[NH:29][C:30]([CH3:31])([CH3:32])[CH2:33]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:5]-[C:4])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[OH;D1;+0:5]) | c1f4c807e3614fe47cd090c6e68b82a7d9ae32f9a7d33334666a7ce8 | 1 | 1 | CC(C)(C)[O-].CCCCCCC.CO.[K+] | 289 |
335,275 | 210,032 | null | Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]#[CH:19])=[C:12]([O:20][CH3:21])[CH:11]=1.C(NC(C)C)(C)C>[Cu]I.O1CCOCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]#[C:19][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=2)=[C:12]([O:20][CH3:21])[CH:11]=1 | null | US20040248739A1_0235 | 2,004 | Br[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][n:20]1.C1COCCO1.CC(C)NC(C)C.[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[O:10][CH2:11][C:12]#[CH:13].[Cu]I>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[O:10][CH2:11][C:12]#[C:13][c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][n:20]1 | 0.982986 | C#CCOc1ccc(F)cc1OC.C1COCCO1.CC(C)NC(C)C.Cc1ccc(Br)nc1.[Cu]I>>COc1cc(F)ccc1OCC#Cc1ccc(C)cn1 | C#CCOc1ccc(F)cc1OC.C1COCCO1.CC(C)NC(C)C.Cc1ccc(Br)nc1.[Cu]I>>COc1cc(F)ccc1OCC#Cc1ccc(C)cn1 | US20040248739A1_0235apps | c5a6f6efaf05af6a96febd8fe47853261dd60759f3e4015ed61ca068 | Br[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][n:20]1.C1COCCO1.CC(C)NC(C)C.[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[O:10][CH2:11][C:12]#[CH:13].[Cu]I | [CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[O:10][CH2:11][C:12]#[C:13][c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][n:20]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[C;H0;D2;+0:5]#[C:4])>>(Br-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]#[CH;D1;+0:5]) | 739e08208e573d7e25ef062d9d0c47deaeb0f84f8ccc1c37253cf426 | 1 | 1 | C1COCCO1.CC(C)NC(C)C.[Cu]I | 777 |
4,885 | 25,141 | 35,606 | [C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(O)=[O:2].S(Cl)([Cl:31])=O>C1C=CC=CC=1>[Cl:31][C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:2] | null | US04066692_ | 1,978 | O=S(Cl)[Cl:24].O[C:22]([CH:10]([CH2:9][CH2:8][CH2:7][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:25][C:26]([CH3:27])=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[O:19][CH2:20][CH3:21])=[O:23].c1ccccc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[O:19][CH2:20][CH3:21])[C:22](=[O:23])[Cl:24])[O:25][C:26]([CH3:27])=[O:28] | 0.555271 | CCCCCC(CCCC(CCCCCCC(=O)OCC)C(=O)O)OC(C)=O.O=S(Cl)Cl.c1ccccc1>>CCCCCC(CCCC(CCCCCCC(=O)OCC)C(=O)Cl)OC(C)=O | CCCCCC(CCCC(CCCCCCC(=O)OCC)C(=O)O)OC(C)=O.O=S(Cl)Cl.c1ccccc1>>CCCCCC(CCCC(CCCCCCC(=O)OCC)C(=O)Cl)OC(C)=O | US04066692_grants | 10171a636d74183c48476a809f4176ec09e560035c3552f77ae84938 | O=S(Cl)[Cl:24].O[C:22]([CH:10]([CH2:9][CH2:8][CH2:7][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:25][C:26]([CH3:27])=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[O:19][CH2:20][CH3:21])=[O:23].c1ccccc1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[O:19][CH2:20][CH3:21])[C:22](=[O:23])[Cl:24])[O:25][C:26]([CH3:27])=[O:28] | ([C:3]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:4])>>(Cl-S(=O)-[Cl;H0;D1;+0:1]).(O-[C;H0;D3;+0:2](-[C:3])=[O;D1;H0:4]) | 876ba1f28c2f41de2ca98cf6279d2d855ebe250e1445dd0bf341762d | 1 | 1 | c1ccccc1 | 53 |
423,125 | 1,786,303 | null | Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[SH:55][CH2:56][CH2:57][OH:58]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([S:55][CH2:56][CH2:57][OH:58])[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1 | |f:4.5.6.7.8| | US20150329523A1_0764 | 2,015 | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:15][c:11]([N+:12](=[O:13])[O-:14])[cH:10]1.C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd].[SH:6][CH2:7][CH2:8][OH:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6][CH2:7][CH2:8][OH:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | 0.979255 | C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.COc1cc(Br)cc([N+](=O)[O-])c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~[Pd]~[Pd].OCCS>>COc1cc(SCCO)cc([N+](=O)[O-])c1 | C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.COc1cc(Br)cc([N+](=O)[O-])c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.OCCS.[Pd].[Pd]>>COc1cc(SCCO)cc([N+](=O)[O-])c1 | US20150329523A1_0764apps | 3114bb5e99ef643068fa5b5ab292a7517c7cd3d0c925fe1db209a3fc | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:15][c:11]([N+:12](=[O:13])[O-:14])[cH:10]1.C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd].[SH:6][CH2:7][CH2:8][OH:9] | [CH3:1][O:2][c:3]1[cH:4][c:5]([S:6][CH2:7][CH2:8][OH:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | ([C:4]-[S;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[SH;D1;+0:5]) | 0832399050bd2e3d5c0553fd5a3c0b80a51a60006d375056ca8f45be | 1 | 1 | C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd] | 824 |
112,737 | 423,828 | 722,265 | [C:1]([C:4]1[C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[S:12][C:8]=2[CH:7]=[C:6]([O:21]C)[CH:5]=1)([OH:3])=[O:2].B(Br)(Br)Br>>[C:1]([C:4]1[C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[S:12][C:8]=2[CH:7]=[C:6]([OH:21])[CH:5]=1)([OH:3])=[O:2] | null | US07045539B2_0159 | 2,006 | BrB(Br)Br.C[O:7][c:6]1[cH:5][c:4]([C:2](=[O:1])[OH:3])[c:20]2[c:9]([cH:8]1)[s:10][c:11](-[c:12]1[cH:13][cH:14][c:15]([O:16]C)[cH:17][cH:18]1)[n:19]2>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([OH:7])[cH:8][c:9]2[s:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([OH:16])[cH:17][cH:18]3)[n:19][c:20]12 | 0.872264 | BrB(Br)Br.COc1ccc(-c2nc3c(C(=O)O)cc(OC)cc3s2)cc1>>O=C(O)c1cc(O)cc2sc(-c3ccc(O)cc3)nc12 | BrB(Br)Br.COc1ccc(-c2nc3c(C(=O)O)cc(OC)cc3s2)cc1>>O=C(O)c1cc(O)cc2sc(-c3ccc(O)cc3)nc12 | US07045539B2_0159grants | 3899ce06b904a7efc8cc6292a67db722501a113404350728e7957a43 | BrB(Br)Br.C[O:7][c:6]1[cH:5][c:4]([C:2](=[O:1])[OH:3])[c:20]2[c:9]([cH:8]1)[s:10][c:11](-[c:12]1[cH:13][cH:14][c:15]([O:16]C)[cH:17][cH:18]1)[n:19]2 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([OH:7])[cH:8][c:9]2[s:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([OH:16])[cH:17][cH:18]3)[n:19][c:20]12 | ([OH;D1;+0:1]-[c:2].[OH;D1;+0:3]-[c:4])>>(C-[O;H0;D2;+0:1]-[c:2].C-[O;H0;D2;+0:3]-[c:4]) | d1f5fe893669d3e53b2812239ed33bc7f23228b96208d35ecd887e17 | 0 | 1 | BrB(Br)Br | 20 |
342,324 | 349,065 | null | CO.[BH4-].[Li+].[C:5]([O:9][C:10]([N:12]1[CH2:16][CH:15]=[CH:14][C@H:13]1[CH2:17][C:18](OC)=[O:19])=[O:11])([CH3:8])([CH3:7])[CH3:6].O>O1CCCC1>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH:15]=[CH:14][C@H:13]1[CH2:17][CH2:18][OH:19])=[O:11])([CH3:8])([CH3:7])[CH3:6] | |f:1.2| | US20060100431A1_2302 | 2,006 | C1CCOC1.CO.CO[C:14]([CH2:13][C@H:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]=[CH:11]1)=[O:15].O.[BH4-].[Li+]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[CH:11][C@H:12]1[CH2:13][CH2:14][OH:15] | 0.30475 | C1CCOC1.CO.COC(=O)C[C@@H]1C=CCN1C(=O)OC(C)(C)C.O.[BH4-]~[Li+]>>CC(C)(C)OC(=O)N1CC=C[C@H]1CCO | C1CCOC1.CO.COC(=O)C[C@@H]1C=CCN1C(=O)OC(C)(C)C.O.[BH4-].[Li+]>>CC(C)(C)OC(=O)N1CC=C[C@H]1CCO | US20060100431A1_2302apps | d9b1176e78a53cef704b148d7b035be5b7f0ffc1f168cde7eb3a9cfa | C1CCOC1.CO.CO[C:14]([CH2:13][C@H:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]=[CH:11]1)=[O:15].O.[BH4-].[Li+] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[CH:11][C@H:12]1[CH2:13][CH2:14][OH:15] | ([C:2]-[CH2;D2;+0:1]-[OH;D1;+0:3])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;H0;D1;+0:3]) | ace077327b65885e2493775e77cea5434d2da2918de8308af58629a6 | 1 | 1 | C1CCOC1.CO.O.[BH4-].[Li+] | 343 |
142,031 | 511,918 | 858,435 | [N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH:26]=1.O>CN(C)C=O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:25]2[CH:24]=[N:23][CH:22]=[C:21]([CH2:20][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[N:2]4)=[CH:15][CH:14]=3)[CH:26]=2)=[CH:32][CH:31]=1 | |f:1.2| | US07429605B2_0667 | 2,008 | CN(C)C=O.Cl[CH2:11][c:10]1[cH:9][n:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:30][cH:29]2)[cH:28]1.O.[H-].[Na+].[OH:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH2:18][CH2:19][CH2:20][n:21]2[cH:22][cH:23][n:24][n:25]2)[cH:26][cH:27]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][cH:9][c:10]([CH2:11][O:12][c:13]3[cH:14][cH:15][c:16]([CH2:17][CH2:18][CH2:19][CH2:20][n:21]4[cH:22][cH:23][n:24][n:25]4)[cH:26][cH:27]3)[cH:28]2)[cH:29][cH:30]1 | 0.907487 | CN(C)C=O.ClCc1cncc(-c2ccc(Cl)cc2)c1.O.Oc1ccc(CCCCn2ccnn2)cc1.[H-]~[Na+]>>Clc1ccc(-c2cncc(COc3ccc(CCCCn4ccnn4)cc3)c2)cc1 | CN(C)C=O.ClCc1cncc(-c2ccc(Cl)cc2)c1.O.Oc1ccc(CCCCn2ccnn2)cc1.[H-].[Na+]>>Clc1ccc(-c2cncc(COc3ccc(CCCCn4ccnn4)cc3)c2)cc1 | US07429605B2_0667grants | 0142b88c99f759babbb21fa191e246a2bf560b416abffd1e5bb01b83 | CN(C)C=O.Cl[CH2:11][c:10]1[cH:9][n:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:30][cH:29]2)[cH:28]1.O.[H-].[Na+].[OH:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH2:18][CH2:19][CH2:20][n:21]2[cH:22][cH:23][n:24][n:25]2)[cH:26][cH:27]1 | [Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][cH:9][c:10]([CH2:11][O:12][c:13]3[cH:14][cH:15][c:16]([CH2:17][CH2:18][CH2:19][CH2:20][n:21]4[cH:22][cH:23][n:24][n:25]4)[cH:26][cH:27]3)[cH:28]2)[cH:29][cH:30]1 | ([#7;a:4]:[c:3]:[c:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6])>>(Cl-[CH2;D2;+0:1]-[c:2]:[c:3]:[#7;a:4]).([OH;D1;+0:5]-[c:6]) | 959e87ef3b08913b6e9aa3d1f5f93b702c24b32b0fb9a7e635d68608 | 1 | 1 | CN(C)C=O.O.[H-].[Na+] | 678 |
79,997 | 323,662 | 548,383 | [Br:1][CH2:2][CH2:3][C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](O)=[O:6].S(Cl)([Cl:22])=O.CN(C)C=O>C(Cl)(Cl)Cl>[Br:1][CH2:2][CH2:3][C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([Cl:22])=[O:6] | null | US06362203B1_ | 2,002 | CN(C)C=O.ClC(Cl)Cl.O=S(Cl)[Cl:3].O[C:2](=[O:1])[C:4]([CH2:5][CH2:6][Br:7])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[O:1]=[C:2]([Cl:3])[C:4]([CH2:5][CH2:6][Br:7])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | 0.339424 | CN(C)C=O.ClC(Cl)Cl.O=C(O)C(CCBr)(c1ccccc1)c1ccccc1.O=S(Cl)Cl>>O=C(Cl)C(CCBr)(c1ccccc1)c1ccccc1 | CN(C)C=O.ClC(Cl)Cl.O=C(O)C(CCBr)(c1ccccc1)c1ccccc1.O=S(Cl)Cl>>O=C(Cl)C(CCBr)(c1ccccc1)c1ccccc1 | US06362203B1_grants | 9a64b22e5a47eae2a959a0d27ebae3a34a576c3cd6bf57d070ae7f44 | CN(C)C=O.ClC(Cl)Cl.O=S(Cl)[Cl:3].O[C:2](=[O:1])[C:4]([CH2:5][CH2:6][Br:7])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | [O:1]=[C:2]([Cl:3])[C:4]([CH2:5][CH2:6][Br:7])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | ([C:3]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:4])>>(Cl-S(=O)-[Cl;H0;D1;+0:1]).(O-[C;H0;D3;+0:2](-[C:3])=[O;D1;H0:4]) | 876ba1f28c2f41de2ca98cf6279d2d855ebe250e1445dd0bf341762d | 1 | 1 | CN(C)C=O.ClC(Cl)Cl | 53 |
399,937 | 1,370,870 | null | [CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[BH4-].[Na+]>C1COCC1.CO.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[OH:12])=[CH:5][CH:4]=1 | |f:1.2| | US20130131034A1_0367 | 2,013 | C1CCOC1.CO.O.[BH4-].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:12]2.[Na+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([OH:10])[CH2:11][CH2:12]2 | 0.963958 | C1CCOC1.CO.COc1ccc2c(c1)C(=O)CC2.O.[BH4-]~[Na+]>>COc1ccc2c(c1)C(O)CC2 | C1CCOC1.CO.COc1ccc2c(c1)C(=O)CC2.O.[BH4-].[Na+]>>COc1ccc2c(c1)C(O)CC2 | US20130131034A1_0367apps | 8e0a974fc12046265f8d9ff9d71ed7225e2f65e10374068060a0fbda | C1CCOC1.CO.O.[BH4-].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:12]2.[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([OH:10])[CH2:11][CH2:12]2 | ([C:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4])>>([C:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]) | e79b9f0e956cb38254670cbba4f53d0c22148efe9b15465e130440fe | 1 | 1 | C1CCOC1.CO.O.[BH4-].[Na+] | 24 |
133,175 | 484,634 | 816,226 | Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[N:6][CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>>[N:11]12[CH2:16][CH2:15][CH:14]([CH2:13][CH2:12]1)[CH:9]([O:8][C:5]1[N:6]=[CH:7][C:2]([C:22]3[CH:23]=[C:18]([CH:19]=[CH:20][CH:21]=3)[NH2:17])=[CH:3][CH:4]=1)[CH2:10]2 | null | US07309699B2_0234 | 2,007 | Br[c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]2[CH2:13][N:14]3[CH2:15][CH2:16][CH:17]2[CH2:18][CH2:19]3)[n:20][cH:21]1.OB(O)[c:6]1[cH:5][cH:4][cH:3][c:2]([NH2:1])[cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][N:14]4[CH2:15][CH2:16][CH:17]3[CH2:18][CH2:19]4)[n:20][cH:21]2)[cH:22]1 | 0.97545 | Brc1ccc(OC2CN3CCC2CC3)nc1.Nc1cccc(B(O)O)c1>>Nc1cccc(-c2ccc(OC3CN4CCC3CC4)nc2)c1 | Brc1ccc(OC2CN3CCC2CC3)nc1.Nc1cccc(B(O)O)c1>>Nc1cccc(-c2ccc(OC3CN4CCC3CC4)nc2)c1 | US07309699B2_0234grants | 1c8f2f76c5cbc7e0101ab051edadde96c1af60d8715acd0333a7b88a | Br[c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]2[CH2:13][N:14]3[CH2:15][CH2:16][CH:17]2[CH2:18][CH2:19]3)[n:20][cH:21]1.OB(O)[c:6]1[cH:5][cH:4][cH:3][c:2]([NH2:1])[cH:22]1 | [NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][N:14]4[CH2:15][CH2:16][CH:17]3[CH2:18][CH2:19]4)[n:20][cH:21]2)[cH:22]1 | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[c:2])-[c;H0;D3;+0:5](:[c:6]):[c:7])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]:[#7;a:4]).(O-B(-O)-[c;H0;D3;+0:5](:[c:6]):[c:7]) | d9e3b3a2cfe6e8e4f2db101af24fed0e1646b47d310510c8f6dc03e2 | 1 | 1 | null | 833 |
425,062 | 1,803,444 | null | Br[C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[B:13]1([B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1.CC([O-])=O.[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:8][C:6]1[CH:5]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:3]=[C:2]([B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)[CH:7]=1 | |f:2.3,5.6.7.8| | US20150361100A1_0778 | 2,015 | Br[c:6]1[cH:7][c:8]([F:9])[cH:10][c:11]([S:12]([NH2:13])(=[O:14])=[O:15])[cH:16]1.C1COCCO1.CC(=O)[O-].CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:18]([CH3:19])([CH3:20])[O:17]2)OC1(C)C.Cl[Pd]Cl.[Fe+2].[K+].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][c:8]([F:9])[cH:10][c:11]([S:12]([NH2:13])(=[O:14])=[O:15])[cH:16]2)[O:17][C:18]1([CH3:19])[CH3:20] | 0.107421 | C1COCCO1.CC(=O)[O-]~[K+].CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.Cl[Pd]Cl~[Fe+2]~c1ccc(P(c2ccccc2)[c-]2cccc2)cc1~c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.NS(=O)(=O)c1cc(F)cc(Br)c1>>CC1(C)OB(c2cc(F)cc(S(N)(=O)=O)c2)OC1(C)C | C1COCCO1.CC(=O)[O-].CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.Cl[Pd]Cl.NS(=O)(=O)c1cc(F)cc(Br)c1.[Fe+2].[K+].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1>>CC1(C)OB(c2cc(F)cc(S(N)(=O)=O)c2)OC1(C)C | US20150361100A1_0778apps | 83688bdcf93a282532fbc0fbc9c4706752c2d21d63879d0896b36b42 | Br[c:6]1[cH:7][c:8]([F:9])[cH:10][c:11]([S:12]([NH2:13])(=[O:14])=[O:15])[cH:16]1.C1COCCO1.CC(=O)[O-].CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:18]([CH3:19])([CH3:20])[O:17]2)OC1(C)C.Cl[Pd]Cl.[Fe+2].[K+].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | [CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][c:8]([F:9])[cH:10][c:11]([S:12]([NH2:13])(=[O:14])=[O:15])[cH:16]2)[O:17][C:18]1([CH3:19])[CH3:20] | ([#8:5]-[B;H0;D3;+0:4](-[#8:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(C-C1(-C)-O-B(-[B;H0;D3;+0:4](-[#8:5])-[#8:6])-O-C-1(-C)-C) | 809111b01e38b549ab34d8fc095aeb8c0540db06f3c41a247745e882 | 1 | 1 | C1COCCO1.CC(=O)[O-].Cl[Pd]Cl.[Fe+2].[K+].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | 942 |
54,113 | 233,391 | 389,950 | [CH3:1][C@@:2]12[C@H:12]3[CH2:13][CH2:14][C@:15]4([CH3:21])[C@@H:19]([OH:20])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C@H:8]1[CH2:7][C:5](=[O:6])[CH2:4][CH2:3]2.C(N(CC)CC)C.[Cl:29][CH2:30][C:31](Cl)=[O:32]>C(Cl)Cl.ClCl>[Cl:29][CH2:30][C:31]([O:20][C@H:19]1[CH2:18][CH2:17][C@H:16]2[C@H:11]3[C@H:12]([CH2:13][CH2:14][C@:15]12[CH3:21])[C@:2]1([CH3:1])[C@H:8]([CH2:7][C:5](=[O:6])[CH2:4][CH2:3]1)[CH2:9][CH2:10]3)=[O:32] | null | US05691307_ | 1,997 | CCN(CC)CC.ClCCl.ClCl.Cl[C:19](=[O:20])[CH2:21][Cl:22].[CH3:1][C@:2]12[CH2:3][CH2:4][C:5](=[O:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([OH:18])[CH2:23][CH2:24][C@@H:25]12>>[CH3:1][C@:2]12[CH2:3][CH2:4][C:5](=[O:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([O:18][C:19](=[O:20])[CH2:21][Cl:22])[CH2:23][CH2:24][C@@H:25]12 | 0.864936 | CCN(CC)CC.C[C@]12CCC(=O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12.ClCCl.ClCl.O=C(Cl)CCl>>C[C@]12CCC(=O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](OC(=O)CCl)[C@@]3(C)CC[C@@H]12 | CCN(CC)CC.C[C@]12CCC(=O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12.ClCCl.ClCl.O=C(Cl)CCl>>C[C@]12CCC(=O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](OC(=O)CCl)[C@@]3(C)CC[C@@H]12 | US05691307_grants | 10d3674946d2f2f029747816b64c965fddcf71d60c51f8ef466f2084 | CCN(CC)CC.ClCCl.ClCl.Cl[C:19](=[O:20])[CH2:21][Cl:22].[CH3:1][C@:2]12[CH2:3][CH2:4][C:5](=[O:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([OH:18])[CH2:23][CH2:24][C@@H:25]12 | [CH3:1][C@:2]12[CH2:3][CH2:4][C:5](=[O:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([O:18][C:19](=[O:20])[CH2:21][Cl:22])[CH2:23][CH2:24][C@@H:25]12 | ([C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[OH;D1;+0:5]) | dd95e42df91c7014b8bb61b2fcc1694968b310b2018cb51dbcc5f881 | 1 | 1 | CCN(CC)CC.ClCCl.ClCl | 126 |
280,419 | 918,225 | 1,535,724 | [Br:1][C:2]([CH3:7])([CH3:6])[C:3](Br)=[O:4].[CH3:8][C:9]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:10]=1[NH2:11].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]([CH3:7])([CH3:6])[C:3]([NH:11][C:10]1[C:12]([CH3:17])=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=1[CH3:8])=[O:4] | null | US08877936B2_0105 | 2,014 | Br[C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[Br:13].CCN(CC)CC.ClCCl.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH2:7])[c:14]([CH3:15])[cH:16]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[Br:13])[c:14]([CH3:15])[cH:16]1 | 0.603553 | CC(C)(Br)C(=O)Br.CCN(CC)CC.Cc1cc(C)c(N)c(C)c1.ClCCl>>Cc1cc(C)c(NC(=O)C(C)(C)Br)c(C)c1 | CC(C)(Br)C(=O)Br.CCN(CC)CC.Cc1cc(C)c(N)c(C)c1.ClCCl>>Cc1cc(C)c(NC(=O)C(C)(C)Br)c(C)c1 | US08877936B2_0105grants | dec7ed294afb5a48b8d18db1eed9109a437d8843fdf6657691400e82 | Br[C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[Br:13].CCN(CC)CC.ClCCl.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH2:7])[c:14]([CH3:15])[cH:16]1 | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[Br:13])[c:14]([CH3:15])[cH:16]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(Br-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | 8ab04841592f589cf1861a16fea6663af1db3cbfa5e5cb1096e666bd | 1 | 1 | CCN(CC)CC.ClCCl | 442 |
18,144 | 88,316 | 143,945 | [CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][CH2:15][C:16](=[O:18])[CH3:17].[BH4-].[Na+]>CO>[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][CH2:15][CH:16]([OH:18])[CH3:17] | |f:1.2| | US04581377_ | 1,986 | CO.[BH4-].[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1-2.[Na+]>>[CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1-2 | 0.978151 | CC(=O)CCc1ccc2c(c1)Cc1ccccc1-2.CO.[BH4-]~[Na+]>>CC(O)CCc1ccc2c(c1)Cc1ccccc1-2 | CC(=O)CCc1ccc2c(c1)Cc1ccccc1-2.CO.[BH4-].[Na+]>>CC(O)CCc1ccc2c(c1)Cc1ccccc1-2 | US04581377_grants | bcaccc17754aa845f9924a5799246bbd9906dd4d6aa39972e36d174c | CO.[BH4-].[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1-2.[Na+] | [CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1-2 | ([C:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[OH;D1;+0:4])>>([C:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[O;H0;D1;+0:4]) | 0fb396942a5bc824558e6936c3618c2e342b489a89eccebed032da69 | 1 | 1 | CO.[BH4-].[Na+] | 91 |
119,402 | 444,265 | 755,282 | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.C1(C)C=CC=CC=1.C(N(CC)CC)C.ClC(Cl)(O[C:43](=[O:49])[O:44][C:45](Cl)(Cl)Cl)Cl.[CH3:51][O:52][C:53]1[CH:63]=[CH:62][CH:61]=[CH:60][C:54]=1[O:55][CH2:56][CH2:57]CO>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH:20][C:43](=[O:49])[O:44][CH2:45][CH2:57][CH2:56][O:55][C:54]2[CH:60]=[CH:61][CH:62]=[CH:63][C:53]=2[O:52][CH3:51])=[C:18]([CH3:24])[CH:17]=1 | |f:1.2| | US07135466B2_0565 | 2,006 | CCN(CC)CC.Cc1ccccc1.ClC(Cl)(Cl)O[C:17](OC(Cl)(Cl)Cl)=[O:18].ClCCl.[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][c:13]([CH3:14])[c:15]([NH2:16])[cH:32][c:33]3[CH3:34])[c:35]2[cH:36][c:37]1[O:38][CH3:39].[OH:19][CH2:20][CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1[O:30][CH3:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][c:13]([CH3:14])[c:15]([NH:16][C:17](=[O:18])[O:19][CH2:20][CH2:21][CH2:22][O:23][c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]4[O:30][CH3:31])[cH:32][c:33]3[CH3:34])[c:35]2[cH:36][c:37]1[O:38][CH3:39] | 0.865983 | CCN(CC)CC~Cc1ccccc1.COc1cc2nccc(Oc3cc(C)c(N)cc3C)c2cc1OC.COc1ccccc1OCCCO.ClCCl.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>COc1cc2nccc(Oc3cc(C)c(NC(=O)OCCCOc4ccccc4OC)cc3C)c2cc1OC | CCN(CC)CC.COc1cc2nccc(Oc3cc(C)c(N)cc3C)c2cc1OC.COc1ccccc1OCCCO.Cc1ccccc1.ClCCl.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>COc1cc2nccc(Oc3cc(C)c(NC(=O)OCCCOc4ccccc4OC)cc3C)c2cc1OC | US07135466B2_0565grants | ed47288448917dc4b2c5990c0675b579989c2b1b4e4d310486e00265 | CCN(CC)CC.Cc1ccccc1.ClC(Cl)(Cl)O[C:17](OC(Cl)(Cl)Cl)=[O:18].ClCCl.[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][c:13]([CH3:14])[c:15]([NH2:16])[cH:32][c:33]3[CH3:34])[c:35]2[cH:36][c:37]1[O:38][CH3:39].[OH:19][CH2:20][CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1[O:30][CH3:31] | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][c:13]([CH3:14])[c:15]([NH:16][C:17](=[O:18])[O:19][CH2:20][CH2:21][CH2:22][O:23][c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]4[O:30][CH3:31])[cH:32][c:33]3[CH3:34])[c:35]2[cH:36][c:37]1[O:38][CH3:39] | ([C:3]-[O;H0;D2;+0:4]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[c:9](-[#8:10]-[c:11]):[c:12]:[c:13]:1)>>(Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl).([C:3]-[OH;D1;+0:4]).([NH2;D1;+0:5]-[c:6]1:[c:7]:[c:8]:[c:9](-[#8:10]-[c:11]):[c:12]:[c:13]:1) | 402380ff45e48ddb3018bdf49f6be73d6020bd02f8650e48fd44f2d3 | 1 | 1 | CCN(CC)CC.Cc1ccccc1.ClCCl | 960 |
259,355 | 857,349 | 1,426,523 | [NH2:1][C:2]1[CH:7]=[C:6](O)[N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1.P(Cl)(Cl)([Cl:20])=O>>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:20])[N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1 | null | US08653266B2_0059 | 2,014 | O=P(Cl)(Cl)[Cl:14].O[c:13]1[cH:12][c:10]([NH2:11])[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:17][cH:16]2)[n:15]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH2:11])[cH:12][c:13]([Cl:14])[n:15]2)[cH:16][cH:17]1 | 0.361169 | N#Cc1ccc(Nc2nc(N)cc(O)n2)cc1.O=P(Cl)(Cl)Cl>>N#Cc1ccc(Nc2nc(N)cc(Cl)n2)cc1 | N#Cc1ccc(Nc2nc(N)cc(O)n2)cc1.O=P(Cl)(Cl)Cl>>N#Cc1ccc(Nc2nc(N)cc(Cl)n2)cc1 | US08653266B2_0059grants | 68375d3c43b47e42de5f2f42a3f98287ffe148b7a05043a922ef9543 | O=P(Cl)(Cl)[Cl:14].O[c:13]1[cH:12][c:10]([NH2:11])[n:9][c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:17][cH:16]2)[n:15]1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH2:11])[cH:12][c:13]([Cl:14])[n:15]2)[cH:16][cH:17]1 | ([Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1)>>(Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1]).(O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1) | a2c64018c076fa0d60fc56cbb584c832e508c8e1e501d501fcc59a1b | 1 | 1 | null | 25 |
206,661 | 700,664 | 1,154,588 | [NH2:1][CH2:2][C@H:3]1[N:10]([C:11]([C:13]2[N:14]=[C:15]([CH3:25])[S:16][C:17]=2[C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[O:12])[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][CH:6]([CH3:26])[CH2:7]2.[Cl:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([CH:36]=1)[C:33](O)=[O:34]>>[Cl:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([CH:36]=1)[C:33]([NH:1][CH2:2][C@H:3]1[N:10]([C:11]([C:13]2[N:14]=[C:15]([CH3:25])[S:16][C:17]=2[C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[O:12])[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][CH:6]([CH3:26])[CH2:7]2)=[O:34] | null | US08106215B2_0454 | 2,012 | O[C:26](=[O:27])[c:28]1[cH:29][n:30][cH:31][c:32]([Cl:33])[cH:34]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[s:8][c:9]([CH3:10])[n:11][c:12]2[C:13](=[O:14])[N:15]2[CH2:16][C@@H:17]3[CH2:18][CH:19]([CH3:20])[CH2:21][C@@H:22]3[C@H:23]2[CH2:24][NH2:25])[cH:35]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[s:8][c:9]([CH3:10])[n:11][c:12]2[C:13](=[O:14])[N:15]2[CH2:16][C@@H:17]3[CH2:18][CH:19]([CH3:20])[CH2:21][C@@H:22]3[C@H:23]2[CH2:24][NH:25][C:26](=[O:27])[c:28]2[cH:29][n:30][cH:31][c:32]([Cl:33])[cH:34]2)[cH:35]1 | 0.911275 | Cc1cccc(-c2sc(C)nc2C(=O)N2C[C@@H]3CC(C)C[C@@H]3[C@H]2CN)c1.O=C(O)c1cncc(Cl)c1>>Cc1cccc(-c2sc(C)nc2C(=O)N2C[C@@H]3CC(C)C[C@@H]3[C@H]2CNC(=O)c2cncc(Cl)c2)c1 | Cc1cccc(-c2sc(C)nc2C(=O)N2C[C@@H]3CC(C)C[C@@H]3[C@H]2CN)c1.O=C(O)c1cncc(Cl)c1>>Cc1cccc(-c2sc(C)nc2C(=O)N2C[C@@H]3CC(C)C[C@@H]3[C@H]2CNC(=O)c2cncc(Cl)c2)c1 | US08106215B2_0454grants | 9be840355133962f771366fa84bdeed99eca490e800eff53a1aa0584 | O[C:26](=[O:27])[c:28]1[cH:29][n:30][cH:31][c:32]([Cl:33])[cH:34]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[s:8][c:9]([CH3:10])[n:11][c:12]2[C:13](=[O:14])[N:15]2[CH2:16][C@@H:17]3[CH2:18][CH:19]([CH3:20])[CH2:21][C@@H:22]3[C@H:23]2[CH2:24][NH2:25])[cH:35]1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[s:8][c:9]([CH3:10])[n:11][c:12]2[C:13](=[O:14])[N:15]2[CH2:16][C@@H:17]3[CH2:18][CH:19]([CH3:20])[CH2:21][C@@H:22]3[C@H:23]2[CH2:24][NH:25][C:26](=[O:27])[c:28]2[cH:29][n:30][cH:31][c:32]([Cl:33])[cH:34]2)[cH:35]1 | ([#7;a:5]:[c:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[c:4]:[#7;a:5]).([C:6]-[NH2;D1;+0:7]) | c8d3e8be644ca37fe3075935d6d9f9515443e1dc5a5fca512a1988ac | 1 | 1 | null | 674 |
126,974 | 466,831 | 790,864 | [CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([CH:27]=[O:28])[C:14]=2[CH3:29])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([CH2:27][OH:28])[C:14]=2[CH3:29])=[CH:9][CH:10]=1 | |f:1.2| | US07226951B2_0783 | 2,007 | CO.[BH4-].[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([O:20][CH:21]([CH3:22])[CH3:23])[c:24]([CH:25]=[O:26])[c:27]2[CH3:28])[cH:29][cH:30]1.[Na+]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([O:20][CH:21]([CH3:22])[CH3:23])[c:24]([CH2:25][OH:26])[c:27]2[CH3:28])[cH:29][cH:30]1 | 0.402067 | CO.COC(=O)Cc1ccc(C#Cc2cc(C(C)(C)C)c(OC(C)C)c(C=O)c2C)cc1.[BH4-]~[Na+]>>COC(=O)Cc1ccc(C#Cc2cc(C(C)(C)C)c(OC(C)C)c(CO)c2C)cc1 | CO.COC(=O)Cc1ccc(C#Cc2cc(C(C)(C)C)c(OC(C)C)c(C=O)c2C)cc1.[BH4-].[Na+]>>COC(=O)Cc1ccc(C#Cc2cc(C(C)(C)C)c(OC(C)C)c(CO)c2C)cc1 | US07226951B2_0783grants | 2b38e66d3a112087300262d2fa0ade0b97760a8379e1ac48b83389de | CO.[BH4-].[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([O:20][CH:21]([CH3:22])[CH3:23])[c:24]([CH:25]=[O:26])[c:27]2[CH3:28])[cH:29][cH:30]1.[Na+] | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([O:20][CH:21]([CH3:22])[CH3:23])[c:24]([CH2:25][OH:26])[c:27]2[CH3:28])[cH:29][cH:30]1 | ([OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3])>>([O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]) | 840c26c06ae3d1e03b5c3844632a3543b6d18e6db9d7ee28fbdda31c | 1 | 1 | CO.[BH4-].[Na+] | 356 |
363,274 | 663,488 | null | Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[CH:8]2[CH2:11][CH2:12][CH2:13][N:7]2[C:6]1=[O:14].[O:15]1[C:19]2[C:20]([N:24]3[CH2:29][CH2:28][NH:27][C@@H:26]([CH3:30])[CH2:25]3)=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=[CH:16]1>>[O:15]1[C:19]2[C:20]([N:24]3[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][N:5]4[C:9](=[O:10])[CH:8]5[CH2:11][CH2:12][CH2:13][N:7]5[C:6]4=[O:14])[C@@H:26]([CH3:30])[CH2:25]3)=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=[CH:16]1 | null | US20090036455A1_0149 | 2,009 | Br[CH2:17][CH2:18][CH2:19][N:20]1[C:21](=[O:22])[CH:23]2[CH2:24][CH2:25][CH2:26][N:27]2[C:28]1=[O:29].[CH3:1][C@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][o:12][c:13]23)[CH2:14][CH2:15][NH:16]1>>[CH3:1][C@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][o:12][c:13]23)[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][N:20]1[C:21](=[O:22])[CH:23]2[CH2:24][CH2:25][CH2:26][N:27]2[C:28]1=[O:29] | 0.980913 | C[C@H]1CN(c2cccc3ccoc23)CCN1.O=C1C2CCCN2C(=O)N1CCCBr>>C[C@H]1CN(c2cccc3ccoc23)CCN1CCCN1C(=O)C2CCCN2C1=O | C[C@H]1CN(c2cccc3ccoc23)CCN1.O=C1C2CCCN2C(=O)N1CCCBr>>C[C@H]1CN(c2cccc3ccoc23)CCN1CCCN1C(=O)C2CCCN2C1=O | US20090036455A1_0149apps | f19a43d9e0543525ba79ec3a24c9719cc093c7d11708549f12984014 | Br[CH2:17][CH2:18][CH2:19][N:20]1[C:21](=[O:22])[CH:23]2[CH2:24][CH2:25][CH2:26][N:27]2[C:28]1=[O:29].[CH3:1][C@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][o:12][c:13]23)[CH2:14][CH2:15][NH:16]1 | [CH3:1][C@H:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][o:12][c:13]23)[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][N:20]1[C:21](=[O:22])[CH:23]2[CH2:24][CH2:25][CH2:26][N:27]2[C:28]1=[O:29] | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[C:2])>>(Br-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | 53994dd2d8bb14288cdfb7c2951155e80ca49e2c98f7d531177a38b3 | 0.25 | 4 | null | 73 |
313,148 | 1,017,874 | 1,723,264 | [F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:20]=[C:19]([CH3:30])[C:18]=2[CH3:31])=[C:13]([F:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].[OH-].[Na+]>C1COCC1.CO.CCOC(C)=O>[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:20]=[C:19]([CH3:30])[C:18]=2[CH3:31])=[C:13]([F:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7] | |f:1.2| | US09249085B2_0678 | 2,016 | C1CCOC1.CCOC(C)=O.CC[O:26][C:24]([CH2:23][O:22][c:21]1[cH:20][cH:19][c:17]([F:18])[c:16]([NH:15][CH2:14][c:13]2[cH:12][c:4](-[c:5]3[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]3)[cH:3][c:2]([CH3:1])[c:29]2[CH3:30])[c:27]1[F:28])=[O:25].CO.[Na+].[OH-]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]2)[cH:12][c:13]([CH2:14][NH:15][c:16]2[c:17]([F:18])[cH:19][cH:20][c:21]([O:22][CH2:23][C:24](=[O:25])[OH:26])[c:27]2[F:28])[c:29]1[CH3:30] | 0.946257 | C1CCOC1.CCOC(=O)COc1ccc(F)c(NCc2cc(-c3cccc(F)c3)cc(C)c2C)c1F.CCOC(C)=O.CO.[Na+]~[OH-]>>Cc1cc(-c2cccc(F)c2)cc(CNc2c(F)ccc(OCC(=O)O)c2F)c1C | C1CCOC1.CCOC(=O)COc1ccc(F)c(NCc2cc(-c3cccc(F)c3)cc(C)c2C)c1F.CCOC(C)=O.CO.[Na+].[OH-]>>Cc1cc(-c2cccc(F)c2)cc(CNc2c(F)ccc(OCC(=O)O)c2F)c1C | US09249085B2_0678grants | 400e45435443aba5e30c94981ecfb5dcf8ba163ed647745b997b6ff5 | C1CCOC1.CCOC(C)=O.CC[O:26][C:24]([CH2:23][O:22][c:21]1[cH:20][cH:19][c:17]([F:18])[c:16]([NH:15][CH2:14][c:13]2[cH:12][c:4](-[c:5]3[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]3)[cH:3][c:2]([CH3:1])[c:29]2[CH3:30])[c:27]1[F:28])=[O:25].CO.[Na+].[OH-] | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]2)[cH:12][c:13]([CH2:14][NH:15][c:16]2[c:17]([F:18])[cH:19][cH:20][c:21]([O:22][CH2:23][C:24](=[O:25])[OH:26])[c:27]2[F:28])[c:29]1[CH3:30] | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 9a4c5ceadb3b4a753bb8f03491f138cd875a84f1d327e818237f90df | 1 | 1 | C1CCOC1.CCOC(C)=O.CO.[Na+].[OH-] | 7 |
94,491 | 368,663 | 629,362 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16](O)[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([Cl:21])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[N:9]=2)=[CH:4][CH:3]=1 | null | US06660746B1_ | 2,003 | O=P(Cl)(Cl)[Cl:9].O[c:8]1[n:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:18][cH:17]2)[n:12][c:11]2[c:10]1[CH2:16][CH2:15][CH2:14][CH2:13]2>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([Cl:9])[c:10]3[c:11]([n:12]2)[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]1 | 0.274045 | O=P(Cl)(Cl)Cl.Oc1nc(-c2ccc(Cl)cc2)nc2c1CCCC2>>Clc1ccc(-c2nc(Cl)c3c(n2)CCCC3)cc1 | O=P(Cl)(Cl)Cl.Oc1nc(-c2ccc(Cl)cc2)nc2c1CCCC2>>Clc1ccc(-c2nc(Cl)c3c(n2)CCCC3)cc1 | US06660746B1_grants | 634cd7d3af668544a6449901a45631e9c6f17708567dde9dfb934040 | O=P(Cl)(Cl)[Cl:9].O[c:8]1[n:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:18][cH:17]2)[n:12][c:11]2[c:10]1[CH2:16][CH2:15][CH2:14][CH2:13]2 | [Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([Cl:9])[c:10]3[c:11]([n:12]2)[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]1 | ([#7;a:6]:[c:5]:[c:4]:[c;H0;D3;+0:2](:[#7;a:3])-[Cl;H0;D1;+0:1])>>(Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1]).(O-[c;H0;D3;+0:2](:[#7;a:3]):[c:4]:[c:5]:[#7;a:6]) | 07956985ed73b20cc8f7c7ae5459594c1f7b91ddd0c7a0163125a4b3 | 1 | 1 | null | 168 |
357,723 | 592,240 | null | [CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([C:11]#[N:12])[C:8]([N:13]2[CH2:16][CH:15]([C:17]([O:19]C(C)(C)C)=[O:18])[CH2:14]2)=[N:7][C:6]=1[S:24][CH3:25])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:11]([C:9]1[C:8]([N:13]2[CH2:14][CH:15]([C:17]([OH:19])=[O:18])[CH2:16]2)=[N:7][C:6]([S:24][CH3:25])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:26])[CH:10]=1)#[N:12] | |f:1.2| | US20080171732A1_0773 | 2,008 | CC(C)(C)[O:17][C:15]([CH:14]1[CH2:13][N:12]([c:11]2[c:8]([C:9]#[N:10])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:20]([S:21][CH3:22])[n:19]2)[CH2:18]1)=[O:16].ClCCl.O=C(O)C(F)(F)F>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([C:9]#[N:10])[c:11]([N:12]2[CH2:13][CH:14]([C:15](=[O:16])[OH:17])[CH2:18]2)[n:19][c:20]1[S:21][CH3:22] | 0.894779 | CCOC(=O)c1cc(C#N)c(N2CC(C(=O)OC(C)(C)C)C2)nc1SC.ClCCl~O=C(O)C(F)(F)F>>CCOC(=O)c1cc(C#N)c(N2CC(C(=O)O)C2)nc1SC | CCOC(=O)c1cc(C#N)c(N2CC(C(=O)OC(C)(C)C)C2)nc1SC.ClCCl.O=C(O)C(F)(F)F>>CCOC(=O)c1cc(C#N)c(N2CC(C(=O)O)C2)nc1SC | US20080171732A1_0773apps | e03e789759e535d9d3a6997cc3606167dfc58881437f52b93710f373 | CC(C)(C)[O:17][C:15]([CH:14]1[CH2:13][N:12]([c:11]2[c:8]([C:9]#[N:10])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:20]([S:21][CH3:22])[n:19]2)[CH2:18]1)=[O:16].ClCCl.O=C(O)C(F)(F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([C:9]#[N:10])[c:11]([N:12]2[CH2:13][CH:14]([C:15](=[O:16])[OH:17])[CH2:18]2)[n:19][c:20]1[S:21][CH3:22] | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | cd4c8dfb74ae00d4ec8387e8837370d2f9fd4ad5e54ff56c9878f839 | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 278 |
34,016 | 154,820 | 248,268 | [CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13](O)=[O:14])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.ClC(OCC(C)C)=O>O1CCCC1>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3] | null | US05102877_ | 1,992 | C1CCOC1.CC(C)COC(=O)Cl.CCN(CC)CC.O=[C:11]([CH:10]1[CH2:9][CH2:8][N:7]([C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH2:14][CH2:13]1)[OH:12]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([CH2:11][OH:12])[CH2:13][CH2:14]1 | 0.643921 | C1CCOC1.C=CCOC(=O)N1CCC(C(=O)O)CC1.CC(C)COC(=O)Cl.CCN(CC)CC>>C=CCOC(=O)N1CCC(CO)CC1 | C1CCOC1.C=CCOC(=O)N1CCC(C(=O)O)CC1.CC(C)COC(=O)Cl.CCN(CC)CC>>C=CCOC(=O)N1CCC(CO)CC1 | US05102877_grants | e0ec5ff02b87fa1d01770e7636db5194b739df2af5da8e37390603f9 | C1CCOC1.CC(C)COC(=O)Cl.CCN(CC)CC.O=[C:11]([CH:10]1[CH2:9][CH2:8][N:7]([C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH2:14][CH2:13]1)[OH:12] | [CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([CH2:11][OH:12])[CH2:13][CH2:14]1 | ([C:2]-[CH2;D2;+0:1]-[O;D1;H1:3])>>(O=[C;H0;D3;+0:1](-[C:2])-[O;D1;H1:3]) | 19ea0b41ce34ad96a8275f097d0c11f47736ca7f973cd7c4aee5b189 | 1 | 1 | C1CCOC1.CC(C)COC(=O)Cl.CCN(CC)CC | 231 |
185,923 | 642,920 | 1,062,927 | C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=2[NH:25][C:26]2[C:27]3[CH:35]=[C:34]([F:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=2[NH:25][C:26]2[C:27]3[CH:35]=[C:34]([F:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:11][CH:10]=1 | null | US07910595B2_1591 | 2,011 | CC(C)(C)OC(=O)[NH:26][c:25]1[cH:24][cH:23][c:22]([S:21][c:20]2[c:12]([NH:11][c:10]3[n:9][cH:8][n:7][c:6]4[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:31]([F:32])[cH:30][c:29]43)[cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]2)[cH:28][cH:27]1.ClCCl.O=C(O)C(F)(F)F>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]2[n:7][cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19][c:20]3[S:21][c:22]3[cH:23][cH:24][c:25]([NH2:26])[cH:27][cH:28]3)[c:29]2[cH:30][c:31]1[F:32] | 0.812112 | CC(C)c1nc2ncnc(Nc3cc(C(=O)O)ccc3Sc3ccc(NC(=O)OC(C)(C)C)cc3)c2cc1F.ClCCl.O=C(O)C(F)(F)F>>CC(C)c1nc2ncnc(Nc3cc(C(=O)O)ccc3Sc3ccc(N)cc3)c2cc1F | CC(C)c1nc2ncnc(Nc3cc(C(=O)O)ccc3Sc3ccc(NC(=O)OC(C)(C)C)cc3)c2cc1F.ClCCl.O=C(O)C(F)(F)F>>CC(C)c1nc2ncnc(Nc3cc(C(=O)O)ccc3Sc3ccc(N)cc3)c2cc1F | US07910595B2_1591grants | 0f9c64a9529e14b1c1060fa1300808d2e03ec59062bdbfa073a5093b | CC(C)(C)OC(=O)[NH:26][c:25]1[cH:24][cH:23][c:22]([S:21][c:20]2[c:12]([NH:11][c:10]3[n:9][cH:8][n:7][c:6]4[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:31]([F:32])[cH:30][c:29]43)[cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]2)[cH:28][cH:27]1.ClCCl.O=C(O)C(F)(F)F | [CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]2[n:7][cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19][c:20]3[S:21][c:22]3[cH:23][cH:24][c:25]([NH2:26])[cH:27][cH:28]3)[c:29]2[cH:30][c:31]1[F:32] | ([NH2;D1;+0:1]-[c:2])>>(C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]) | 5f978a847bba3863bf5fb6d96bfd1d3cace2da93615c40c010102dd5 | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 782 |
55,578 | 238,532 | 400,703 | [CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][C:9](=[O:12])[C:10]=2[CH:11]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][CH:9]([OH:12])[C:10]=2[CH:11]=1 | |f:1.2| | US05726172_ | 1,998 | CO.[BH4-].[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH2:14]2.[Na+]>>[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH:8]([OH:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH2:14]2 | 0.746488 | CO.Cc1cnc2c(c1)C(=O)CC(C)(C)C2.[BH4-]~[Na+]>>Cc1cnc2c(c1)C(O)CC(C)(C)C2 | CO.Cc1cnc2c(c1)C(=O)CC(C)(C)C2.[BH4-].[Na+]>>Cc1cnc2c(c1)C(O)CC(C)(C)C2 | US05726172_grants | 006b93fef36dfd2803e0a905c1977bd90c71f86279efd6b697b59b39 | CO.[BH4-].[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH2:14]2.[Na+] | [CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH:8]([OH:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH2:14]2 | ([#7;a:1]:[c:2]:[c:3]-[CH;D3;+0:4](-[C:5])-[OH;D1;+0:6])>>([#7;a:1]:[c:2]:[c:3]-[C;H0;D3;+0:4](-[C:5])=[O;H0;D1;+0:6]) | 35ae83ddfe300f1467d5d76f76561e4fd30c07e7f98e374d3754486d | 1 | 1 | CO.[BH4-].[Na+] | 449 |
306,019 | 994,723 | 1,679,379 | [C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23](O)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[N:26]1([C:31]2[CH:32]=[C:33]([CH2:37][NH2:38])[CH:34]=[CH:35][CH:36]=2)[CH:30]=[CH:29][N:28]=[CH:27]1>>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([NH:38][CH2:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([N:26]4[CH:30]=[CH:29][N:28]=[CH:27]4)[CH:32]=3)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:3])([CH3:2])[CH3:4] | null | US09156837B2_1074 | 2,015 | O[C:13]([CH2:12][c:11]1[n:10][c:9](-[c:8]2[cH:7][n:6][n:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[c:30]2-[c:31]2[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]2)[s:29][cH:28]1)=[O:14].[NH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[n:22]2[cH:23][cH:24][n:25][cH:26]2)[cH:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[n:5]1[n:6][cH:7][c:8](-[c:9]2[n:10][c:11]([CH2:12][C:13](=[O:14])[NH:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][c:21](-[n:22]4[cH:23][cH:24][n:25][cH:26]4)[cH:27]3)[cH:28][s:29]2)[c:30]1-[c:31]1[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]1 | 0.405363 | CC(C)(C)n1ncc(-c2nc(CC(=O)O)cs2)c1-c1ccc(F)cc1.NCc1cccc(-n2ccnc2)c1>>CC(C)(C)n1ncc(-c2nc(CC(=O)NCc3cccc(-n4ccnc4)c3)cs2)c1-c1ccc(F)cc1 | CC(C)(C)n1ncc(-c2nc(CC(=O)O)cs2)c1-c1ccc(F)cc1.NCc1cccc(-n2ccnc2)c1>>CC(C)(C)n1ncc(-c2nc(CC(=O)NCc3cccc(-n4ccnc4)c3)cs2)c1-c1ccc(F)cc1 | US09156837B2_1074grants | 87722074c51e1810d6e73e40e6da41d6a7cdeb22a860812ee4e6bcd0 | O[C:13]([CH2:12][c:11]1[n:10][c:9](-[c:8]2[cH:7][n:6][n:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[c:30]2-[c:31]2[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]2)[s:29][cH:28]1)=[O:14].[NH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[n:22]2[cH:23][cH:24][n:25][cH:26]2)[cH:27]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[n:5]1[n:6][cH:7][c:8](-[c:9]2[n:10][c:11]([CH2:12][C:13](=[O:14])[NH:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][c:21](-[n:22]4[cH:23][cH:24][n:25][cH:26]4)[cH:27]3)[cH:28][s:29]2)[c:30]1-[c:31]1[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1) | 5ad7c2cc16d6ee5b57312b54d1398a8d361f2cfad0dc66add676f018 | 1 | 1 | null | 599 |
27,071 | 126,044 | 203,784 | [C:1]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH:15][CH2:16][CH:17]([OH:24])[C:18]2[N:19]=[C:20]([Cl:23])[S:21][CH:22]=2)[CH3:14])=[CH:8][CH:7]=1)(O)=[O:2].B.O1CCCC1>>[OH:2][CH2:1][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH:15][CH2:16][CH:17]([OH:24])[C:18]2[N:19]=[C:20]([Cl:23])[S:21][CH:22]=2)[CH3:14])=[CH:8][CH:7]=1 | |f:1.2| | US04886814_ | 1,989 | B.C1CCOC1.O=[C:10]([CH2:9][O:8][c:7]1[cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:14][CH2:15][CH:16]([OH:17])[c:18]2[cH:19][s:20][c:21]([Cl:22])[n:23]2)[cH:13][cH:12]1)[OH:11]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][OH:11])[cH:12][cH:13]1)[NH:14][CH2:15][CH:16]([OH:17])[c:18]1[cH:19][s:20][c:21]([Cl:22])[n:23]1 | 0.712993 | B~C1CCOC1.CC(Cc1ccc(OCC(=O)O)cc1)NCC(O)c1csc(Cl)n1>>CC(Cc1ccc(OCCO)cc1)NCC(O)c1csc(Cl)n1 | B.C1CCOC1.CC(Cc1ccc(OCC(=O)O)cc1)NCC(O)c1csc(Cl)n1>>CC(Cc1ccc(OCCO)cc1)NCC(O)c1csc(Cl)n1 | US04886814_grants | 25eeb892d044b3a6011a5b4e528dc43041c84bdc09481899f55e06e0 | B.C1CCOC1.O=[C:10]([CH2:9][O:8][c:7]1[cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:14][CH2:15][CH:16]([OH:17])[c:18]2[cH:19][s:20][c:21]([Cl:22])[n:23]2)[cH:13][cH:12]1)[OH:11] | [CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][OH:11])[cH:12][cH:13]1)[NH:14][CH2:15][CH:16]([OH:17])[c:18]1[cH:19][s:20][c:21]([Cl:22])[n:23]1 | ([C:2]-[CH2;D2;+0:1]-[O;D1;H1:3])>>(O=[C;H0;D3;+0:1](-[C:2])-[O;D1;H1:3]) | 19ea0b41ce34ad96a8275f097d0c11f47736ca7f973cd7c4aee5b189 | 1 | 1 | B.C1CCOC1 | 231 |
147,634 | 528,734 | 886,172 | [C:1]([NH:11][C@H:12]([C:16]([NH:18][CH:19]([C:24](=[O:27])[CH2:25][F:26])[CH2:20][C:21]([OH:23])=O)=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:28][NH:29][CH3:30].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1.C(OCC)(=O)C>[CH3:28][N:29]([CH3:30])[C:21](=[O:23])[CH2:20][CH:19]([NH:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[C:24](=[O:27])[CH2:25][F:26] | null | US07504382B2_0180 | 2,009 | C1CCOC1.CCN=C=NCCCN(C)C.CCOC(C)=O.O[C:21]([CH2:20][CH:19]([NH:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[C:26](=[O:27])[CH2:28][F:29])=[O:22].On1nnc2ccccc21.[NH:23]([CH3:24])[CH3:25]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[NH:18][CH:19]([CH2:20][C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[C:26](=[O:27])[CH2:28][F:29] | 0.521437 | C1CCOC1.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)O)C(=O)CF.CCN=C=NCCCN(C)C.CCOC(C)=O.CNC.On1nnc2ccccc21>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)N(C)C)C(=O)CF | C1CCOC1.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)O)C(=O)CF.CCN=C=NCCCN(C)C.CCOC(C)=O.CNC.On1nnc2ccccc21>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)N(C)C)C(=O)CF | US07504382B2_0180grants | 00388ea5817cedbe5fb1f399631ba267c88541be0244543ec27901a9 | C1CCOC1.CCN=C=NCCCN(C)C.CCOC(C)=O.O[C:21]([CH2:20][CH:19]([NH:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[C:26](=[O:27])[CH2:28][F:29])=[O:22].On1nnc2ccccc21.[NH:23]([CH3:24])[CH3:25] | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[NH:18][CH:19]([CH2:20][C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[C:26](=[O:27])[CH2:28][F:29] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | C1CCOC1.CCN=C=NCCCN(C)C.CCOC(C)=O.On1nnc2ccccc21 | 146 |
222,909 | 748,306 | 1,231,727 | [F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[NH:8][CH2:9]2)=[CH:4][CH:3]=1.[C:20]([O:24][C:25]([N:27]([CH2:38][CH:39]=O)[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[N+:35]([C:32]1[CH:31]=[CH:30][C:29]([CH2:28][N:27]([CH2:38][CH2:39][N:8]2[CH:7]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=3)[CH2:6][C:5]3[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:9]2)[C:25](=[O:26])[O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:34][CH:33]=1)([O-:37])=[O:36] | null | US08273766B2_1495 | 2,012 | O=[CH:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:30][c:31]1[cH:32][cH:33][c:34]([N+:35](=[O:36])[O-:37])[cH:38][cH:39]1.[NH:11]1[CH2:12][c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]2[CH2:20][CH:21]1[CH2:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][N:11]1[CH2:12][c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]2[CH2:20][CH:21]1[CH2:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[CH2:30][c:31]1[cH:32][cH:33][c:34]([N+:35](=[O:36])[O-:37])[cH:38][cH:39]1 | 0.387714 | CC(C)(C)OC(=O)N(CC=O)Cc1ccc([N+](=O)[O-])cc1.Fc1ccc(CC2Cc3ccc(F)cc3CN2)cc1>>CC(C)(C)OC(=O)N(CCN1Cc2cc(F)ccc2CC1Cc1ccc(F)cc1)Cc1ccc([N+](=O)[O-])cc1 | CC(C)(C)OC(=O)N(CC=O)Cc1ccc([N+](=O)[O-])cc1.Fc1ccc(CC2Cc3ccc(F)cc3CN2)cc1>>CC(C)(C)OC(=O)N(CCN1Cc2cc(F)ccc2CC1Cc1ccc(F)cc1)Cc1ccc([N+](=O)[O-])cc1 | US08273766B2_1495grants | a210bfe6c6bda34fc43a78f44e96c8a92471089ae80c4a6da79fa63f | O=[CH:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:30][c:31]1[cH:32][cH:33][c:34]([N+:35](=[O:36])[O-:37])[cH:38][cH:39]1.[NH:11]1[CH2:12][c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]2[CH2:20][CH:21]1[CH2:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][N:11]1[CH2:12][c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]2[CH2:20][CH:21]1[CH2:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[CH2:30][c:31]1[cH:32][cH:33][c:34]([N+:35](=[O:36])[O-:37])[cH:38][cH:39]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)-[CH2;D2;+0:1]-[C:2])>>(O=[CH;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1) | ab7d8d02d14878ee3a143792b6d5d074e6c185e8abdf2cfc57b98620 | 0.5 | 2 | null | 858 |
58,608 | 249,798 | 421,158 | [F:1][C:2]1[CH:3]=[C:4]([N+:20]([O-])=O)[C:5]2[O:10][CH:9]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH2:8][CH2:7][C:6]=2[CH:19]=1.S1C=CC=C1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]2[O:10][CH:9]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH2:8][CH2:7][C:6]=2[CH:19]=1 | null | US05824682_ | 1,998 | CO.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]2[c:8]1[O:9][CH:10]([CH2:11][O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1)[CH2:19][CH2:20]2.[Pd].c1ccsc1>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]2[c:8]1[O:9][CH:10]([CH2:11][O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1)[CH2:19][CH2:20]2 | 0.985716 | CO.O=[N+]([O-])c1cc(F)cc2c1OC(COC1CCCCO1)CC2.[Pd].c1ccsc1>>Nc1cc(F)cc2c1OC(COC1CCCCO1)CC2 | CO.O=[N+]([O-])c1cc(F)cc2c1OC(COC1CCCCO1)CC2.[Pd].c1ccsc1>>Nc1cc(F)cc2c1OC(COC1CCCCO1)CC2 | US05824682_grants | 037694517f84a0c6353e3f65d02f4c991f20bac643f4c5ea1c231c0e | CO.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]2[c:8]1[O:9][CH:10]([CH2:11][O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1)[CH2:19][CH2:20]2.[Pd].c1ccsc1 | [NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]2[c:8]1[O:9][CH:10]([CH2:11][O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1)[CH2:19][CH2:20]2 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pd].c1ccsc1 | 1 |
278,191 | 912,066 | 1,524,617 | [CH3:1][C:2]([S:28]([CH3:31])(=[O:30])=[O:29])([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][C:16]=1[CH3:27])[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl.O1CCOCC1.CO>ClCCl>[OH:6][NH:5][C:3](=[O:4])[C:2]([CH3:1])([S:28]([CH3:31])(=[O:29])=[O:30])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][C:16]=1[CH3:27] | null | US08853258B2_0253 | 2,014 | C1CCC([O:21][NH:20][C:18]([C:16]([CH2:15][CH2:14][c:13]2[c:2]([CH3:1])[cH:3][c:4](-[c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[cH:11][cH:12]2)([CH3:17])[S:22]([CH3:23])(=[O:24])=[O:25])=[O:19])OC1.C1COCCO1.CO.Cl.ClCCl>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][cH:12][c:13]1[CH2:14][CH2:15][C:16]([CH3:17])([C:18](=[O:19])[NH:20][OH:21])[S:22]([CH3:23])(=[O:24])=[O:25] | 0.632773 | C1COCCO1.CO.Cc1cc(-c2ccccc2)ccc1CCC(C)(C(=O)NOC1CCCCO1)S(C)(=O)=O.Cl.ClCCl>>Cc1cc(-c2ccccc2)ccc1CCC(C)(C(=O)NO)S(C)(=O)=O | C1COCCO1.CO.Cc1cc(-c2ccccc2)ccc1CCC(C)(C(=O)NOC1CCCCO1)S(C)(=O)=O.Cl.ClCCl>>Cc1cc(-c2ccccc2)ccc1CCC(C)(C(=O)NO)S(C)(=O)=O | US08853258B2_0253grants | 6f4f46e6999091ec099064de574dc7909cc076074cb7316ff682eda3 | C1CCC([O:21][NH:20][C:18]([C:16]([CH2:15][CH2:14][c:13]2[c:2]([CH3:1])[cH:3][c:4](-[c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[cH:11][cH:12]2)([CH3:17])[S:22]([CH3:23])(=[O:24])=[O:25])=[O:19])OC1.C1COCCO1.CO.Cl.ClCCl | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][cH:12][c:13]1[CH2:14][CH2:15][C:16]([CH3:17])([C:18](=[O:19])[NH:20][OH:21])[S:22]([CH3:23])(=[O:24])=[O:25] | ([C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[OH;D1;+0:5])>>([C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[O;H0;D2;+0:5]-C1-C-C-C-C-O-1) | 1f2dcb30e19ee306721080fde9035fe8d9cdfdf40b919d6f2a706a05 | 1 | 1 | C1COCCO1.CO.Cl.ClCCl | 915 |
217,562 | 731,917 | 1,205,998 | Cl.[N:2]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[N:19]=[C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:21][C:22]=3[C:23]([F:26])([F:25])[F:24])=[O:17])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=1.C(N(CC)CC)C>CN(C=O)C>[C:27]1([C:20]2[O:21][C:22]([C:23]([F:26])([F:24])[F:25])=[C:18]([C:16]([NH:15][C:12]3[CH:13]=[CH:14][C:9]([N:2]4[CH2:8][CH2:7][CH2:6][N:5]([CH2:34][C:35]5[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=5)[CH2:4][CH2:3]4)=[CH:10][CH:11]=3)=[O:17])[N:19]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1 | |f:0.1| | US08211884B2_0161 | 2,012 | Br[CH2:8][c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:41][cH:40]1.CCN(CC)CC.CN(C)C=O.Cl.[NH:9]1[CH2:10][CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]3[n:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[o:30][c:31]3[C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]2)[CH2:38][CH2:39]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][N:13]([c:14]3[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]4[n:22][c:23](-[c:24]5[cH:25][cH:26][cH:27][cH:28][cH:29]5)[o:30][c:31]4[C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]3)[CH2:38][CH2:39]2)[cH:40][cH:41]1 | 0.210751 | CCN(CC)CC.CN(C)C=O.Cl~O=C(Nc1ccc(N2CCCNCC2)cc1)c1nc(-c2ccccc2)oc1C(F)(F)F.O=C(O)c1ccc(CBr)cc1>>O=C(O)c1ccc(CN2CCCN(c3ccc(NC(=O)c4nc(-c5ccccc5)oc4C(F)(F)F)cc3)CC2)cc1 | CCN(CC)CC.CN(C)C=O.Cl.O=C(Nc1ccc(N2CCCNCC2)cc1)c1nc(-c2ccccc2)oc1C(F)(F)F.O=C(O)c1ccc(CBr)cc1>>O=C(O)c1ccc(CN2CCCN(c3ccc(NC(=O)c4nc(-c5ccccc5)oc4C(F)(F)F)cc3)CC2)cc1 | US08211884B2_0161grants | a0a07c2cc06f2ad5fde79ce9a05d9f2d5ebf3d74f8d04d6fc4bb1324 | Br[CH2:8][c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:41][cH:40]1.CCN(CC)CC.CN(C)C=O.Cl.[NH:9]1[CH2:10][CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]3[n:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[o:30][c:31]3[C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]2)[CH2:38][CH2:39]1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][N:13]([c:14]3[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]4[n:22][c:23](-[c:24]5[cH:25][cH:26][cH:27][cH:28][cH:29]5)[o:30][c:31]4[C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]3)[CH2:38][CH2:39]2)[cH:40][cH:41]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | 83224be0473e190f3e9801b4a42490bc28eb62b70434bda042317a86 | 1 | 1 | CCN(CC)CC.CN(C)C=O.Cl | 248 |
402,763 | 1,462,876 | null | [F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([N:15]3[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:16]3[C:21]([OH:23])=[O:22])[CH:12]=[C:11]([CH2:24][CH2:25][CH3:26])[N:10]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:32](=O)(O)[O-].[Na+]>CO>[CH3:32][O:22][C:21]([C@@H:16]1[CH2:17][C@@H:18]([OH:20])[CH2:19][N:15]1[C:13]1[CH:12]=[C:11]([CH2:24][CH2:25][CH3:26])[N:10]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:14]=1)=[O:23] | |f:2.3| | US20130338179A1_0704 | 2,013 | O=C([O-])O.O=S(=O)(O)O.O[C:13]([C@H:12]1[N:7]([c:6]2[cH:5][c:4]([CH2:3][CH2:2][CH3:1])[n:27][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[n:17]2)[CH2:8][C@H:9]([OH:10])[CH2:11]1)=[O:14].[Na+].[OH:15][CH3:16]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([N:7]2[CH2:8][C@H:9]([OH:10])[CH2:11][C@H:12]2[C:13](=[O:14])[O:15][CH3:16])[n:17][c:18]([NH:19][c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[n:27]1 | 0.652381 | CCCc1cc(N2C[C@H](O)C[C@H]2C(=O)O)nc(Nc2ccc(F)cc2)n1.CO.O=C([O-])O~[Na+].O=S(=O)(O)O>>CCCc1cc(N2C[C@H](O)C[C@H]2C(=O)OC)nc(Nc2ccc(F)cc2)n1 | CCCc1cc(N2C[C@H](O)C[C@H]2C(=O)O)nc(Nc2ccc(F)cc2)n1.CO.O=C([O-])O.O=S(=O)(O)O.[Na+]>>CCCc1cc(N2C[C@H](O)C[C@H]2C(=O)OC)nc(Nc2ccc(F)cc2)n1 | US20130338179A1_0704apps | 2203dd87a81724354ee69c2800f99ee8e0728cf27f098f19f270d357 | O=C([O-])O.O=S(=O)(O)O.O[C:13]([C@H:12]1[N:7]([c:6]2[cH:5][c:4]([CH2:3][CH2:2][CH3:1])[n:27][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[n:17]2)[CH2:8][C@H:9]([OH:10])[CH2:11]1)=[O:14].[Na+].[OH:15][CH3:16] | [CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([N:7]2[CH2:8][C@H:9]([OH:10])[CH2:11][C@H:12]2[C:13](=[O:14])[O:15][CH3:16])[n:17][c:18]([NH:19][c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[n:27]1 | ([#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[C;D1;H3:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]).([C;D1;H3:5]-[OH;D1;+0:6]) | 935c394e1172191386450814994167815202f162836daf4714e9adc8 | 1 | 1 | O=C([O-])O.O=S(=O)(O)O.[Na+] | 536 |
129,073 | 472,941 | 799,324 | [CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:19])=[CH:10][C:9]=1[CH3:20])[CH3:6])[CH3:2].I[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1>>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]#[C:19][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[CH:10][C:9]=1[CH3:20])[CH3:6])[CH3:2] | null | US07253192B2_0301 | 2,007 | I[c:20]1[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:19])[cH:30][c:31]1[CH3:32]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]#[C:19][c:20]2[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]2)[cH:30][c:31]1[CH3:32] | 0.175058 | C#CCCCOc1ccc(OC(C)(C)C(=O)OCC)c(C)c1.FC(F)(F)c1ccc(I)cc1>>CCOC(=O)C(C)(C)Oc1ccc(OCCCC#Cc2ccc(C(F)(F)F)cc2)cc1C | C#CCCCOc1ccc(OC(C)(C)C(=O)OCC)c(C)c1.FC(F)(F)c1ccc(I)cc1>>CCOC(=O)C(C)(C)Oc1ccc(OCCCC#Cc2ccc(C(F)(F)F)cc2)cc1C | US07253192B2_0301grants | d1a41dd53db9582ef3be5beb754e901cd7752c29db42f210f2978bc2 | I[c:20]1[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:19])[cH:30][c:31]1[CH3:32] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]#[C:19][c:20]2[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]2)[cH:30][c:31]1[CH3:32] | ([C:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(I-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]#[CH;D1;+0:5]) | 342ec13d6dc46f8caedd04911cf98542ef6704fb7da33fd6b60ef2c6 | 1 | 1 | null | 664 |
125,423 | 461,951 | 781,887 | [C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][CH3:23])=[C:14]([CH2:24][OH:25])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:28](Br)[CH3:29]>>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][CH3:23])=[C:14]([CH2:24][O:25][CH2:28][CH3:29])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4] | |f:1.2| | US07208494B2_0468 | 2,007 | Br[CH2:2][CH3:1].[H-].[Na+].[OH:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]1[CH2:11][CH3:12])[N:13]1[C@H:14]([CH3:15])[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][C@H:26]1[CH2:27]2>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]1[CH2:11][CH3:12])[N:13]1[C@H:14]([CH3:15])[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][C@H:26]1[CH2:27]2 | 0.392349 | CCBr.CCc1nc2c(cc1CO)C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@@H](C)N21.[H-]~[Na+]>>CCOCc1cc2c(nc1CC)N1[C@H](C)CN(C(=O)OC(C)(C)C)C[C@H]1C2 | CCBr.CCc1nc2c(cc1CO)C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@@H](C)N21.[H-].[Na+]>>CCOCc1cc2c(nc1CC)N1[C@H](C)CN(C(=O)OC(C)(C)C)C[C@H]1C2 | US07208494B2_0468grants | fd564741c201fc8d1a010f0042949d307d98c364bdacb4cb8eeacad7 | Br[CH2:2][CH3:1].[H-].[Na+].[OH:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]1[CH2:11][CH3:12])[N:13]1[C@H:14]([CH3:15])[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][C@H:26]1[CH2:27]2 | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]1[CH2:11][CH3:12])[N:13]1[C@H:14]([CH3:15])[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][C@H:26]1[CH2:27]2 | ([C:3]-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C;D1;H3:2])>>(Br-[CH2;D2;+0:1]-[C;D1;H3:2]).([C:3]-[OH;D1;+0:4]) | a4c3d230363503c3cdd0e8b3bb15c888472ef0fddbf2cfc06e03712b | 1 | 1 | [H-].[Na+] | 95 |
117,267 | 437,697 | 744,809 | [CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4].N1C=CC=CC=1.C(N(CC)CC)C.[C:35](Cl)(=[O:43])[O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C)C=O>[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:35](=[O:43])[O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4] | null | US07109219B2_0447 | 2,006 | CCN(CC)CC.CN(C)C=O.Cl[C:18](=[O:19])[O:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[CH3:1][NH:2][C:3](=[O:4])[n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10]([O:11][c:12]3[cH:13][cH:14][n:15][c:16]([NH2:17])[cH:27]3)[cH:28][cH:29][c:30]12.c1ccncc1>>[CH3:1][NH:2][C:3](=[O:4])[n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10]([O:11][c:12]3[cH:13][cH:14][n:15][c:16]([NH:17][C:18](=[O:19])[O:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[cH:27]3)[cH:28][cH:29][c:30]12 | 0.856877 | CCN(CC)CC.CN(C)C=O.CNC(=O)n1ccc2cc(Oc3ccnc(N)c3)ccc21.O=C(Cl)Oc1ccccc1.c1ccncc1>>CNC(=O)n1ccc2cc(Oc3ccnc(NC(=O)Oc4ccccc4)c3)ccc21 | CCN(CC)CC.CN(C)C=O.CNC(=O)n1ccc2cc(Oc3ccnc(N)c3)ccc21.O=C(Cl)Oc1ccccc1.c1ccncc1>>CNC(=O)n1ccc2cc(Oc3ccnc(NC(=O)Oc4ccccc4)c3)ccc21 | US07109219B2_0447grants | eaf52a5f270ea5c4a1ff3df068ace75ca53652df67ad4570647869d9 | CCN(CC)CC.CN(C)C=O.Cl[C:18](=[O:19])[O:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[CH3:1][NH:2][C:3](=[O:4])[n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10]([O:11][c:12]3[cH:13][cH:14][n:15][c:16]([NH2:17])[cH:27]3)[cH:28][cH:29][c:30]12.c1ccncc1 | [CH3:1][NH:2][C:3](=[O:4])[n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10]([O:11][c:12]3[cH:13][cH:14][n:15][c:16]([NH:17][C:18](=[O:19])[O:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[cH:27]3)[cH:28][cH:29][c:30]12 | ([#7;a:4]:[c:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[#8:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[#8:2])=[O;D1;H0:3]).([#7;a:4]:[c:5]-[NH2;D1;+0:6]) | cbeb297cfb63c2efd22a42eb3173a1c7fc388b44165ab8056c873259 | 1 | 1 | CCN(CC)CC.CN(C)C=O.c1ccncc1 | 502 |
167,808 | 589,638 | 977,989 | Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.[F:12][C:13]1([F:17])[CH2:16][NH:15][CH2:14]1.C(N(C(C)C)CC)(C)C>C1COCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:16][C:13]([F:17])([F:12])[CH2:14]2)=[N:3][CH:4]=1)([O-:10])=[O:9] | |f:1.2| | US07714126B2_0205 | 2,010 | C1CCOC1.CCN(C(C)C)C(C)C.Cl.Cl[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:15][n:14]1.[NH:8]1[CH2:9][C:10]([F:11])([F:12])[CH2:13]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][C:10]([F:11])([F:12])[CH2:13]2)[n:14][cH:15]1 | 0.333203 | C1CCOC1.CCN(C(C)C)C(C)C.Cl~FC1(F)CNC1.O=[N+]([O-])c1ccc(Cl)nc1>>O=[N+]([O-])c1ccc(N2CC(F)(F)C2)nc1 | C1CCOC1.CCN(C(C)C)C(C)C.Cl.FC1(F)CNC1.O=[N+]([O-])c1ccc(Cl)nc1>>O=[N+]([O-])c1ccc(N2CC(F)(F)C2)nc1 | US07714126B2_0205grants | 08ba5537020e904f970562cdbe2d21c7ba2507f546a144d736fb36c4 | C1CCOC1.CCN(C(C)C)C(C)C.Cl.Cl[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:15][n:14]1.[NH:8]1[CH2:9][C:10]([F:11])([F:12])[CH2:13]1 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][C:10]([F:11])([F:12])[CH2:13]2)[n:14][cH:15]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | d775cf39c89817610201eb77d7f2c05750999ab6870ec4bcf35a0a78 | 1 | 1 | C1CCOC1.CCN(C(C)C)C(C)C.Cl | 220 |
56,930 | 243,576 | 410,348 | [C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[Na+].O>CCO>[O:7]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][Br:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | |f:2.3| | US05760259_ | 1,998 | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1].CCO.O.[Na+].[OH-].[OH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | 0.666283 | BrCCCCCCCBr.CCO.O.Oc1ccccc1.[Na+]~[OH-]>>BrCCCCCCCOc1ccccc1 | BrCCCCCCCBr.CCO.O.Oc1ccccc1.[Na+].[OH-]>>BrCCCCCCCOc1ccccc1 | US05760259_grants | 46d5feb682f99f66d087ea38a4724d7203f49103e3409c4281c54aee | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1].CCO.O.[Na+].[OH-].[OH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | [Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(Br-[CH2;D2;+0:1]-[C:2]).([OH;D1;+0:3]-[c:4]) | 77cefa6f7285e1367b00e291ad0c233a215688d867a7713380b3385d | 1 | 1 | CCO.O.[Na+].[OH-] | 75 |
78,883 | 319,234 | 541,133 | [CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7](Cl)[N:6]=1)[CH:2]=[CH2:3].[CH2:19]([NH2:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>O>[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH:26][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:6]=1)[CH:2]=[CH2:3] | null | US06339089B2_ | 2,002 | Cl[c:7]1[n:6][c:5]([NH:4][CH2:3][CH:2]=[CH2:1])[c:25]2[c:17]([n:16]1)[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24]2.O.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[CH2:1]=[CH:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[n:16][c:17]2[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][c:25]12 | 0.961238 | C=CCNc1nc(Cl)nc2ccc([N+](=O)[O-])cc12.CCCCCCCN.O>>C=CCNc1nc(NCCCCCCC)nc2ccc([N+](=O)[O-])cc12 | C=CCNc1nc(Cl)nc2ccc([N+](=O)[O-])cc12.CCCCCCCN.O>>C=CCNc1nc(NCCCCCCC)nc2ccc([N+](=O)[O-])cc12 | US06339089B2_grants | 17a3fc4a351ec2e3639148419769928dd64c9b355e1d1a1088630612 | Cl[c:7]1[n:6][c:5]([NH:4][CH2:3][CH:2]=[CH2:1])[c:25]2[c:17]([n:16]1)[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24]2.O.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15] | [CH2:1]=[CH:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[n:16][c:17]2[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][c:25]12 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[NH;D2;+0:5]-[C:4])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C:4]-[NH2;D1;+0:5]) | 37356f3ff9da6e71c10e8b10fe57838cb502f1ab49d9cb2b73931baa | 1 | 1 | O | 544 |
236,649 | 789,723 | 1,306,550 | [F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[C:23]([F:26])([F:25])[F:24])[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14]C)=[O:13])[CH2:9][CH2:8][N:7]1[C:16]([O:18][CH3:19])=[O:17].[Br-].[Li+].C(N(CC)CC)C>C(#N)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[C:23]([F:26])([F:24])[F:25])[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9][CH2:8][N:7]1[C:16]([O:18][CH3:19])=[O:17] | |f:1.2| | US08415378B2_0503 | 2,013 | CC#N.CCN(CC)CC.C[O:11][C:9]([CH:8]1[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[c:23]([F:24])[cH:25]2)[CH2:12]1)=[O:10].O.[Br-].[Li+]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12][CH:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[c:23]([F:24])[cH:25]1 | 0.303864 | CC#N.CCN(CC)CC.COC(=O)C1CCN(C(=O)OC)C(Cc2ccc(C(F)(F)F)c(F)c2)C1.O.[Br-]~[Li+]>>COC(=O)N1CCC(C(=O)O)CC1Cc1ccc(C(F)(F)F)c(F)c1 | CC#N.CCN(CC)CC.COC(=O)C1CCN(C(=O)OC)C(Cc2ccc(C(F)(F)F)c(F)c2)C1.O.[Br-].[Li+]>>COC(=O)N1CCC(C(=O)O)CC1Cc1ccc(C(F)(F)F)c(F)c1 | US08415378B2_0503grants | ba15e8b5c8ab2dc64ad4c35fc9ea4264cb6b1fb05427d2a31b849473 | CC#N.CCN(CC)CC.C[O:11][C:9]([CH:8]1[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[c:23]([F:24])[cH:25]2)[CH2:12]1)=[O:10].O.[Br-].[Li+] | [CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12][CH:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[c:23]([F:24])[cH:25]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | CC#N.CCN(CC)CC.O.[Br-].[Li+] | 88 |
127,007 | 466,904 | 790,967 | [Cl:1][CH2:2][C:3]([OH:5])=[O:4].[CH3:6][CH:7]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH2:8][CH2:9]O>[OH-].[K+].O>[CH2:9]([O:4][C:3](=[O:5])[CH2:2][Cl:1])[CH2:8][CH:7]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:6] | |f:2.3| | US07229958B2_0095 | 2,007 | O.O[C:12](=[O:13])[CH2:14][Cl:15].[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][OH:11].[K+].[OH-]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][O:11][C:12](=[O:13])[CH2:14][Cl:15] | 0.474393 | CC(C)=CCCC(C)CCO.O.O=C(O)CCl.[K+]~[OH-]>>CC(C)=CCCC(C)CCOC(=O)CCl | CC(C)=CCCC(C)CCO.O.O=C(O)CCl.[K+].[OH-]>>CC(C)=CCCC(C)CCOC(=O)CCl | US07229958B2_0095grants | 7ce6bba4077757bf0ed89f82e9b84235ba6718c70c457165875e4e29 | O.O[C:12](=[O:13])[CH2:14][Cl:15].[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][OH:11].[K+].[OH-] | [CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][O:11][C:12](=[O:13])[CH2:14][Cl:15] | ([C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[OH;D1;+0:5]) | a6871142fd86a88cf89e8dce15586c0c2325bd32f2c5592778c4dcb1 | 1 | 1 | O.[K+].[OH-] | 17 |
89,737 | 353,998 | 603,757 | [Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[CH:20]=[C:19](I)[CH:18]=[N:17][C:13]=3[N:14]([CH3:16])[N:15]=2)=[O:9])=[CH:4][CH:3]=1.C(NCC)C.[CH2:30]([OH:33])[C:31]#[CH:32]>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[CH:20]=[C:19]([C:32]#[C:31][CH2:30][OH:33])[CH:18]=[N:17][C:13]=3[N:14]([CH3:16])[N:15]=2)=[O:9])=[CH:4][CH:3]=1 | |^1:42,61| | US06559145B2_ | 2,003 | CCNCC.CCOC(C)=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.I[c:20]1[cH:19][c:18]2[c:16](=[O:17])[c:4]([C:5](=[O:6])[NH:7][CH2:8][c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[n:3][n:2]([CH3:1])[c:27]2[n:26][cH:25]1.[CH:21]#[C:22][CH2:23][OH:24].[Cu]I>>[CH3:1][n:2]1[n:3][c:4]([C:5](=[O:6])[NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[c:16](=[O:17])[c:18]2[cH:19][c:20]([C:21]#[C:22][CH2:23][OH:24])[cH:25][n:26][c:27]12 | 0.972031 | C#CCO.CCNCC.CCOC(C)=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1nc(C(=O)NCc2ccc(Cl)cc2)c(=O)c2cc(I)cnc21.[Cu]I>>Cn1nc(C(=O)NCc2ccc(Cl)cc2)c(=O)c2cc(C#CCO)cnc21 | C#CCO.CCNCC.CCOC(C)=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1nc(C(=O)NCc2ccc(Cl)cc2)c(=O)c2cc(I)cnc21.[Cu]I>>Cn1nc(C(=O)NCc2ccc(Cl)cc2)c(=O)c2cc(C#CCO)cnc21 | US06559145B2_grants | 77f5997dc3ce57dc5bedcd82938d16e7a58c8e3ddb8e288c10166872 | CCNCC.CCOC(C)=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.I[c:20]1[cH:19][c:18]2[c:16](=[O:17])[c:4]([C:5](=[O:6])[NH:7][CH2:8][c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[n:3][n:2]([CH3:1])[c:27]2[n:26][cH:25]1.[CH:21]#[C:22][CH2:23][OH:24].[Cu]I | [CH3:1][n:2]1[n:3][c:4]([C:5](=[O:6])[NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[c:16](=[O:17])[c:18]2[cH:19][c:20]([C:21]#[C:22][CH2:23][OH:24])[cH:25][n:26][c:27]12 | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[c:2])-[C;H0;D2;+0:6]#[C:5])>>(I-[c;H0;D3;+0:1](:[c:2]):[c:3]:[#7;a:4]).([C:5]#[CH;D1;+0:6]) | cd3e89f85cc7407d9fd1d71a162d8d4ff1000705bdc49b131afb1118 | 1 | 1 | CCNCC.CCOC(C)=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I | 819 |
192,973 | 663,704 | 1,098,079 | C1COCC1.[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[N:9]=1.[F:19][C:20]([F:29])([F:28])[CH:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1>CCCCCC>[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:24]3([OH:27])[CH2:23][CH2:22][CH:21]([C:20]([F:28])([F:29])[F:19])[CH2:26][CH2:25]3)[CH:14]=2)[N:9]=1 | null | US07989472B2_0266 | 2,011 | Br[c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:23][c:22]2[cH:21][cH:20]1.C1CCOC1.CCCCCC.[C:9]1(=[O:10])[CH2:11][CH2:12][CH:13]([C:14]([F:15])([F:16])[F:17])[CH2:18][CH2:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C:9]3([OH:10])[CH2:11][CH2:12][CH:13]([C:14]([F:15])([F:16])[F:17])[CH2:18][CH2:19]3)[cH:20][cH:21][c:22]2[n:23]1 | 0.369789 | C1CCOC1.CCCCCC.COc1ccc2cc(Br)ccc2n1.O=C1CCC(C(F)(F)F)CC1>>COc1ccc2cc(C3(O)CCC(C(F)(F)F)CC3)ccc2n1 | C1CCOC1.CCCCCC.COc1ccc2cc(Br)ccc2n1.O=C1CCC(C(F)(F)F)CC1>>COc1ccc2cc(C3(O)CCC(C(F)(F)F)CC3)ccc2n1 | US07989472B2_0266grants | 78665e31f9e9cea07ec54854cd5db2113199725484edd767d922e09e | Br[c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:23][c:22]2[cH:21][cH:20]1.C1CCOC1.CCCCCC.[C:9]1(=[O:10])[CH2:11][CH2:12][CH:13]([C:14]([F:15])([F:16])[F:17])[CH2:18][CH2:19]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C:9]3([OH:10])[CH2:11][CH2:12][CH:13]([C:14]([F:15])([F:16])[F:17])[CH2:18][CH2:19]3)[cH:20][cH:21][c:22]2[n:23]1 | ([C:4]-[C;H0;D4;+0:5](-[C:6])(-[OH;D1;+0:7])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[C;H0;D3;+0:5](-[C:6])=[O;H0;D1;+0:7]) | 41129b1fdbb7e14ef56a510a07494eda92c461b8f7356ca675c16192 | 1 | 1 | C1CCOC1.CCCCCC | 321 |
315,693 | 1,026,133 | 1,737,578 | [NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:20]([CH3:22])[CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH:17]=2)[C:15]#[N:16])=[CH:4][N:3]=1.[OH-:23].[Na+]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:20]([CH3:22])[CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH:17]=2)[C:15]([NH2:16])=[O:23])=[CH:4][N:3]=1 | |f:1.2| | US09284279B2_0172 | 2,016 | CCO.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[NH2:18])[cH:19][c:20]1[C:21]#[N:22].[Na+].[OH-:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[NH2:18])[cH:19][c:20]1[C:21]([NH2:22])=[O:23] | 0.500405 | CCO.COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C#N.[Na+]~[OH-]>>COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C(N)=O | CCO.COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C#N.[Na+].[OH-]>>COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C(N)=O | US09284279B2_0172grants | 12fbeec1859cfbf0fe4844004ae1a3f8bbd4033c4ce7f8219e13554e | CCO.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[NH2:18])[cH:19][c:20]1[C:21]#[N:22].[Na+].[OH-:23] | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[NH2:18])[cH:19][c:20]1[C:21]([NH2:22])=[O:23] | ([NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:4])-[c:3])>>([N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]).([OH-;D0:4]) | 2ed02672bae573e00611ba33c4b3d2d4e3138ba402b9d47114ae418e | 1 | 1 | CCO.[Na+] | 419 |
422,867 | 1,781,527 | null | [OH-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[Cl:12][CH2:13][CH2:14]Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:12][CH2:13][CH2:14][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1 | |f:0.1,4.5| | US20150322024A1_0174 | 2,015 | CCCC[N+](CCCC)(CCCC)CCCC.Cl[CH2:3][CH2:2][Cl:1].O=S(=O)([O-])O.[Na+].[OH-].[nH:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12>>[Cl:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | 0.745223 | CCCC[N+](CCCC)(CCCC)CCCC~O=S(=O)([O-])O.ClCCCl.[Na+]~[OH-].c1ccc2[nH]ccc2c1>>ClCCn1ccc2ccccc21 | CCCC[N+](CCCC)(CCCC)CCCC.ClCCCl.O=S(=O)([O-])O.[Na+].[OH-].c1ccc2[nH]ccc2c1>>ClCCn1ccc2ccccc21 | US20150322024A1_0174apps | d66cb823dd288f2f573a9c9d49519b823064890fe4322bf3dd980bd8 | CCCC[N+](CCCC)(CCCC)CCCC.Cl[CH2:3][CH2:2][Cl:1].O=S(=O)([O-])O.[Na+].[OH-].[nH:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | [Cl:1][CH2:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | ([C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:4](:[c:3]):[c:5])>>(Cl-[CH2;D2;+0:1]-[C:2]).([c:3]:[nH;D2;+0:4]:[c:5]) | 8da12b15fc45fa8b5b0ee6c5fd933779aabc22db8c3073b0baf5d6d7 | 1 | 1 | CCCC[N+](CCCC)(CCCC)CCCC.O=S(=O)([O-])O.[Na+].[OH-] | 42 |
150,744 | 538,598 | 902,401 | [CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][NH2:12].C(O)(=O)C.[BH4-].[Na+]>CO>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:1][NH:12][CH3:11] | |f:3.4| | US07541357B2_2257 | 2,009 | CC(=O)O.CO.O=[CH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][CH3:11].[BH4-].[CH3:1][NH2:2].[Na+]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][CH3:11] | 0.976253 | CC(=O)O.CN.CO.COc1ccccc1C=O.[BH4-]~[Na+]>>CNCc1ccccc1OC | CC(=O)O.CN.CO.COc1ccccc1C=O.[BH4-].[Na+]>>CNCc1ccccc1OC | US07541357B2_2257grants | 957a00dc0e786f473ea016d5eff34cdb8521fae147cb4794f6a5a131 | CC(=O)O.CO.O=[CH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][CH3:11].[BH4-].[CH3:1][NH2:2].[Na+] | [CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][CH3:11] | ([C;D1;H3:3]-[NH;D2;+0:4]-[CH2;D2;+0:1]-[c:2])>>(O=[CH;D2;+0:1]-[c:2]).([C;D1;H3:3]-[NH2;D1;+0:4]) | f78624bd87f224b709b14a27d6ee712af84642974d7873cf47c74b30 | 1 | 1 | CC(=O)O.CO.[BH4-].[Na+] | 468 |
366,608 | 704,480 | null | [F:1][C:2]1[CH:39]=[N:38][C:5]2[N:6]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33](I)[CH:32]=3)[C:7](=[O:30])[N:8]([C@@H:11]3[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([C:20]4[N:21]=[C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]5[CH:29]=4)=[O:19])[CH2:13][CH2:12]3)[C:9](=[O:10])[C:4]=2[CH:3]=1.[CH:40]([C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1)=[O:41]>>[F:1][C:2]1[CH:39]=[N:38][C:5]2[N:6]([C:31]3[CH:32]=[C:33]([C:45]4[CH:46]=[CH:47][C:42]([CH:40]=[O:41])=[CH:43][CH:44]=4)[CH:34]=[CH:35][CH:36]=3)[C:7](=[O:30])[N:8]([C@@H:11]3[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([C:20]4[N:21]=[C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]5[CH:29]=4)=[O:19])[CH2:13][CH2:12]3)[C:9](=[O:10])[C:4]=2[CH:3]=1 | null | US20090124596A1_0821 | 2,009 | I[c:31]1[cH:30][cH:29][cH:28][c:27](-[n:26]2[c:25]3[c:19]([c:17](=[O:18])[n:16]([C@H:15]4[CH2:14][CH2:13][C@@H:12]([NH:11][C:9]([c:8]5[n:7][c:6]6[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:46]6[cH:45]5)=[O:10])[CH2:44][CH2:43]4)[c:41]2=[O:42])[cH:20][c:21]([F:22])[cH:23][n:24]3)[cH:40]1.OB(O)[c:32]1[cH:33][cH:34][c:35]([CH:36]=[O:37])[cH:38][cH:39]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[n:7][c:8]([C:9](=[O:10])[NH:11][C@H:12]3[CH2:13][CH2:14][C@@H:15]([n:16]4[c:17](=[O:18])[c:19]5[cH:20][c:21]([F:22])[cH:23][n:24][c:25]5[n:26](-[c:27]5[cH:28][cH:29][cH:30][c:31](-[c:32]6[cH:33][cH:34][c:35]([CH:36]=[O:37])[cH:38][cH:39]6)[cH:40]5)[c:41]4=[O:42])[CH2:43][CH2:44]3)[cH:45][n:46]12 | 0.878718 | Cc1cccc2nc(C(=O)N[C@H]3CC[C@@H](n4c(=O)c5cc(F)cnc5n(-c5cccc(I)c5)c4=O)CC3)cn12.O=Cc1ccc(B(O)O)cc1>>Cc1cccc2nc(C(=O)N[C@H]3CC[C@@H](n4c(=O)c5cc(F)cnc5n(-c5cccc(-c6ccc(C=O)cc6)c5)c4=O)CC3)cn12 | Cc1cccc2nc(C(=O)N[C@H]3CC[C@@H](n4c(=O)c5cc(F)cnc5n(-c5cccc(I)c5)c4=O)CC3)cn12.O=Cc1ccc(B(O)O)cc1>>Cc1cccc2nc(C(=O)N[C@H]3CC[C@@H](n4c(=O)c5cc(F)cnc5n(-c5cccc(-c6ccc(C=O)cc6)c5)c4=O)CC3)cn12 | US20090124596A1_0821apps | ab166349efe70ba50f12444b0f258986a455218085967ef7c772c919 | I[c:31]1[cH:30][cH:29][cH:28][c:27](-[n:26]2[c:25]3[c:19]([c:17](=[O:18])[n:16]([C@H:15]4[CH2:14][CH2:13][C@@H:12]([NH:11][C:9]([c:8]5[n:7][c:6]6[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:46]6[cH:45]5)=[O:10])[CH2:44][CH2:43]4)[c:41]2=[O:42])[cH:20][c:21]([F:22])[cH:23][n:24]3)[cH:40]1.OB(O)[c:32]1[cH:33][cH:34][c:35]([CH:36]=[O:37])[cH:38][cH:39]1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[n:7][c:8]([C:9](=[O:10])[NH:11][C@H:12]3[CH2:13][CH2:14][C@@H:15]([n:16]4[c:17](=[O:18])[c:19]5[cH:20][c:21]([F:22])[cH:23][n:24][c:25]5[n:26](-[c:27]5[cH:28][cH:29][cH:30][c:31](-[c:32]6[cH:33][cH:34][c:35]([CH:36]=[O:37])[cH:38][cH:39]6)[cH:40]5)[c:41]4=[O:42])[CH2:43][CH2:44]3)[cH:45][n:46]12 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[c;H0;D3;+0:4](:[c:5]):[c:6])>>(I-[c;H0;D3;+0:1](:[c:2]):[c:3]).(O-B(-O)-[c;H0;D3;+0:4](:[c:5]):[c:6]) | 7dd39e88343158d749428576676d52834a98797b3952df04cfe843cf | 0.5 | 2 | null | 855 |
251,944 | 835,266 | 1,385,159 | Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:6][CH:7]=1.[NH:13]1[CH2:18][CH2:17][C:16]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][CH2:19]2)[CH2:15][CH2:14]1.C(N(CC)CC)C.O>CN(C)C=O>[N:8]1([C:5]2[N:4]=[N:3][C:2]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[O:20][CH2:19]4)[CH2:15][CH2:14]3)=[CH:7][CH:6]=2)[CH:12]=[CH:11][N:10]=[CH:9]1 | null | US08575167B2_1075 | 2,013 | CCN(CC)CC.CN(C)C=O.Cl[c:13]1[cH:14][cH:15][c:16](-[n:17]2[cH:18][cH:19][n:20][cH:21]2)[n:22][n:23]1.O.[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][C:9]21[CH2:10][CH2:11][NH:12][CH2:24][CH2:25]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][C:9]21[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][c:16](-[n:17]3[cH:18][cH:19][n:20][cH:21]3)[n:22][n:23]2)[CH2:24][CH2:25]1 | 0.934278 | CCN(CC)CC.CN(C)C=O.Clc1ccc(-n2ccnc2)nn1.O.c1ccc2c(c1)OCC21CCNCC1>>c1ccc2c(c1)OCC21CCN(c2ccc(-n3ccnc3)nn2)CC1 | CCN(CC)CC.CN(C)C=O.Clc1ccc(-n2ccnc2)nn1.O.c1ccc2c(c1)OCC21CCNCC1>>c1ccc2c(c1)OCC21CCN(c2ccc(-n3ccnc3)nn2)CC1 | US08575167B2_1075grants | 1fddee9b1108da59a552778b66c44cf385046319c2ee1fa3d6dfcc19 | CCN(CC)CC.CN(C)C=O.Cl[c:13]1[cH:14][cH:15][c:16](-[n:17]2[cH:18][cH:19][n:20][cH:21]2)[n:22][n:23]1.O.[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][C:9]21[CH2:10][CH2:11][NH:12][CH2:24][CH2:25]1 | [cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][C:9]21[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][c:16](-[n:17]3[cH:18][cH:19][n:20][cH:21]3)[n:22][n:23]2)[CH2:24][CH2:25]1 | ([#7;a:4]:[#7;a:3]:[c;H0;D3;+0:1](:[c:2])-[N;H0;D3;+0:6](-[C:5])-[C:7])>>(Cl-[c;H0;D3;+0:1](:[c:2]):[#7;a:3]:[#7;a:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | 985a0b0463f88646e6a35c0ff595cbd75ebed1b523deff0ac5075e82 | 1 | 1 | CCN(CC)CC.CN(C)C=O.O | 406 |
238,415 | 795,560 | 1,316,712 | Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][O-:13].[Na+]>CO>[CH3:12][O:13][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1 | |f:1.2| | US08436000B2_0065 | 2,013 | C[O-].Cl[c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[CH3:12].[CH3:1][OH:2].[Na+]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[CH3:12] | 0.753986 | CO.C[O-]~[Na+].Cc1cc([N+](=O)[O-])cnc1Cl>>COc1ncc([N+](=O)[O-])cc1C | CO.C[O-].Cc1cc([N+](=O)[O-])cnc1Cl.[Na+]>>COc1ncc([N+](=O)[O-])cc1C | US08436000B2_0065grants | 62e6c8712a24ec9ce6dd23255b4f44bd783e1e3d8956f6bdcde6f9dc | C[O-].Cl[c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[CH3:12].[CH3:1][OH:2].[Na+] | [CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[CH3:12] | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[O;H0;D2;+0:5]-[C;D1;H3:4])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C;D1;H3:4]-[OH;D1;+0:5]) | 10907cd3c67b89554bc459401febf504bb2680a0918b9d386f58414c | 1 | 1 | C[O-].[Na+] | 433 |
114,884 | 430,039 | 732,981 | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:30][C:31]1[CH:40]=[C:39]2[C:34]([CH:35]=[CH:36][CH:37]=[N:38]2)=[CH:33][CH:32]=1.[OH-].[Na+]>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:30][C:31]1[CH:40]=[C:39]2[C:34]([CH:35]=[CH:36][CH:37]=[N:38]2)=[CH:33][CH:32]=1 | |f:1.2.3,5.6| | US07074800B1_1289 | 2,006 | CN(C)C=O.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.O=C([O-])[O-].[K+].[K+].[Na+].[OH-].[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][cH:14][n:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1 | 0.94736 | CN(C)C=O.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.O=C([O-])[O-]~[K+]~[K+].Oc1ccc2cccnc2c1.[Na+]~[OH-]>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCCCC1 | CN(C)C=O.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.O=C([O-])[O-].Oc1ccc2cccnc2c1.[K+].[K+].[Na+].[OH-]>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCCCC1 | US07074800B1_1289grants | 7c0780f74074af5389f7f7f9ba7c15bed10c0cbb9b121804482d6744 | CN(C)C=O.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.O=C([O-])[O-].[K+].[K+].[Na+].[OH-].[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[cH:17]1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][cH:14][n:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1 | ([c:8]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([OH;D1;+0:7]-[c:8]) | 040e0ed2e2cb4b0b62ba03ad3cfe1c87063db3df80ae4aba792d8767 | 1 | 1 | CN(C)C=O.O=C([O-])[O-].[K+].[K+].[Na+].[OH-] | 668 |
81,538 | 328,732 | 559,001 | [Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[CH2:22][CH:23]([CH3:25])[CH3:24]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[C:13](=[O:16])[N:14]([CH2:22][CH:23]([CH3:25])[CH3:24])[N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9] | null | US06403586B1_ | 2,002 | Br[CH2:19][CH:20]([CH3:21])[CH3:22].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([Cl:15])[cH:16]2)[n:17][nH:18][c:23]1=[O:24]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([Cl:15])[cH:16]2)[n:17][n:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[c:23]1=[O:24] | 0.759244 | CC(C)CBr.COC(=O)c1cc(-c2ccc(OC)c(Cl)c2)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(OC)c(Cl)c2)nn(CC(C)C)c1=O | CC(C)CBr.COC(=O)c1cc(-c2ccc(OC)c(Cl)c2)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(OC)c(Cl)c2)nn(CC(C)C)c1=O | US06403586B1_grants | 71b55f64f6940c4f53dc12939b70824b0ca73562b44562649d487dd1 | Br[CH2:19][CH:20]([CH3:21])[CH3:22].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([Cl:15])[cH:16]2)[n:17][nH:18][c:23]1=[O:24] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([Cl:15])[cH:16]2)[n:17][n:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[c:23]1=[O:24] | ([#7;a:3]:[n;H0;D3;+0:4](:[c:5])-[CH2;D2;+0:1]-[C:2])>>(Br-[CH2;D2;+0:1]-[C:2]).([#7;a:3]:[nH;D2;+0:4]:[c:5]) | 357e7b62b7ce08462d0682ba5ed472fb239475424f9df736b44eb978 | 1 | 1 | null | 577 |
391,854 | 1,188,988 | null | Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[CH:22]1([C:25]([N:27]2[CH2:32][CH2:31][CH:30]([CH2:33][NH2:34])[CH2:29][CH2:28]2)=[O:26])[CH2:24][CH2:23]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH:22]1([C:25]([N:27]2[CH2:28][CH2:29][CH:30]([CH2:33][NH:34][C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([C:11]5[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=5)=[CH:9][N:10]=4)[N:7]=3)[CH2:31][CH2:32]2)=[O:26])[CH2:23][CH2:24]1 | |f:3.4.5.6.7| | US20120058997A1_0227 | 2,012 | Cc1ccccc1.Cl[c:12]1[cH:13][cH:14][c:15]2[n:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29]3)[n:30]2[n:31]1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5]1)[N:6]1[CH2:7][CH2:8][CH:9]([CH2:10][NH2:11])[CH2:32][CH2:33]1.[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5]1)[N:6]1[CH2:7][CH2:8][CH:9]([CH2:10][NH:11][c:12]2[cH:13][cH:14][c:15]3[n:16][cH:17][c:18](-[c:19]4[cH:20][cH:21][cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29]4)[n:30]3[n:31]2)[CH2:32][CH2:33]1 | 0.239598 | Cc1ccccc1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1.NCC1CCN(C(=O)C2CC2)CC1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~[Pd]~[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>>O=C(C1CC1)N1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | Cc1ccccc1.FC(F)(F)Oc1cccc(-c2cnc3ccc(Cl)nn23)c1.NCC1CCN(C(=O)C2CC2)CC1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>>O=C(C1CC1)N1CCC(CNc2ccc3ncc(-c4cccc(OC(F)(F)F)c4)n3n2)CC1 | US20120058997A1_0227apps | e9b89c38898ecfd2df8f590838022a088eb8f91a7fb82674cfef8556 | Cc1ccccc1.Cl[c:12]1[cH:13][cH:14][c:15]2[n:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29]3)[n:30]2[n:31]1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5]1)[N:6]1[CH2:7][CH2:8][CH:9]([CH2:10][NH2:11])[CH2:32][CH2:33]1.[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1 | [O:1]=[C:2]([CH:3]1[CH2:4][CH2:5]1)[N:6]1[CH2:7][CH2:8][CH:9]([CH2:10][NH:11][c:12]2[cH:13][cH:14][c:15]3[n:16][cH:17][c:18](-[c:19]4[cH:20][cH:21][cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29]4)[n:30]3[n:31]2)[CH2:32][CH2:33]1 | ([#7;a:4]:[#7;a:3]:[c;H0;D3;+0:1](:[c:2])-[NH;D2;+0:6]-[C:5])>>(Cl-[c;H0;D3;+0:1](:[c:2]):[#7;a:3]:[#7;a:4]).([C:5]-[NH2;D1;+0:6]) | 5f13446fcb79725f80c90d285f87aecee7fc157d5d335032fedca541 | 1 | 1 | Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1 | 241 |
428,342 | 1,824,306 | null | [CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[Br:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](Cl)[CH:10]=1>C1COCC1.C(OCC)C.O>[Br:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:10]=1 | |f:1.2| | US20160016966A1_0487 | 2,016 | C1CCOC1.CCOCC.Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Br:1])[cH:12]1.O.[H-].[Na+].[OH:7][CH2:8][CH:9]1[CH2:10][CH2:11]1>>[Br:1][c:2]1[cH:3][cH:4][n:5][c:6]([O:7][CH2:8][CH:9]2[CH2:10][CH2:11]2)[cH:12]1 | 0.939057 | C1CCOC1.CCOCC.Clc1cc(Br)ccn1.O.OCC1CC1.[H-]~[Na+]>>Brc1ccnc(OCC2CC2)c1 | C1CCOC1.CCOCC.Clc1cc(Br)ccn1.O.OCC1CC1.[H-].[Na+]>>Brc1ccnc(OCC2CC2)c1 | US20160016966A1_0487apps | e22b40b2ece45407798896bbb89bb25bd078ec5f03fba1f569fd068e | C1CCOC1.CCOCC.Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Br:1])[cH:12]1.O.[H-].[Na+].[OH:7][CH2:8][CH:9]1[CH2:10][CH2:11]1 | [Br:1][c:2]1[cH:3][cH:4][n:5][c:6]([O:7][CH2:8][CH:9]2[CH2:10][CH2:11]2)[cH:12]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[O;H0;D2;+0:5]-[C:4])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[OH;D1;+0:5]) | 10907cd3c67b89554bc459401febf504bb2680a0918b9d386f58414c | 1 | 1 | C1CCOC1.CCOCC.O.[H-].[Na+] | 433 |
293,876 | 956,471 | 1,608,472 | [Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[C:5]#[N:6].[N-:11]=[N+:12]=[N-:13].[Na+]>[Br-].[Zn+2].[Br-]>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:13][N:12]=[N:11][N:6]=2)[CH:7]=[C:8]([Br:10])[CH:9]=1 | |f:1.2,3.4.5| | US09012655B2_0210 | 2,015 | [Br-].[Br-].[Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([C:8]#[N:9])[cH:13]1.[N+:10](=[N-:11])=[N-:12].[Na+].[Zn+2]>>[Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7](-[c:8]2[n:9][n:10][n:11][nH:12]2)[cH:13]1 | 0.353806 | N#Cc1cc(Br)cc(Br)c1.[Br-]~[Br-]~[Zn+2].[N-]=[N+]=[N-]~[Na+]>>Brc1cc(Br)cc(-c2nnn[nH]2)c1 | N#Cc1cc(Br)cc(Br)c1.[Br-].[Br-].[N-]=[N+]=[N-].[Na+].[Zn+2]>>Brc1cc(Br)cc(-c2nnn[nH]2)c1 | US09012655B2_0210grants | 54a6404550b77ae30f5c963b249cbea3f90865e4eaf337b480a4759f | [Br-].[Br-].[Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([C:8]#[N:9])[cH:13]1.[N+:10](=[N-:11])=[N-:12].[Na+].[Zn+2] | [Br:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7](-[c:8]2[n:9][n:10][n:11][nH:12]2)[cH:13]1 | ([c:7]:[c;H0;D3;+0:6](:[c:8])-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:[n;H0;D2;+0:1]:[nH;D2;+0:3]:1)>>([N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3]).([N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]):[c:8]) | 431a27c9befb7567576a1e17a63ccbba84935a85c0bcaace2f78f8e1 | 1 | 1 | [Br-].[Br-].[Na+].[Zn+2] | 390 |
87,452 | 347,896 | 593,203 | [CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-])=O)[CH:9]=2)[CH:3]=1>C(O)C.[Pd]>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=2)=[CH:9][C:10]=1[NH2:15] | null | US06521643B1_ | 2,003 | CCO.O=[N+:13]([O-])[c:12]1[c:10]([CH3:11])[cH:9][cH:8][c:7](-[c:6]2[n:5][cH:4][cH:3][c:2]([CH3:1])[cH:15]2)[cH:14]1.[Pd]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[c:12]([NH2:13])[cH:14]2)[cH:15]1 | 0.9965 | CCO.Cc1ccnc(-c2ccc(C)c([N+](=O)[O-])c2)c1.[Pd]>>Cc1ccnc(-c2ccc(C)c(N)c2)c1 | CCO.Cc1ccnc(-c2ccc(C)c([N+](=O)[O-])c2)c1.[Pd]>>Cc1ccnc(-c2ccc(C)c(N)c2)c1 | US06521643B1_grants | f080c4efaf319530baf1127a4b26cf242bd900cee1ddbd20d1ee7570 | CCO.O=[N+:13]([O-])[c:12]1[c:10]([CH3:11])[cH:9][cH:8][c:7](-[c:6]2[n:5][cH:4][cH:3][c:2]([CH3:1])[cH:15]2)[cH:14]1.[Pd] | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[c:12]([NH2:13])[cH:14]2)[cH:15]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.[Pd] | 1 |
302,081 | 982,656 | 1,655,531 | Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[N:3]=1.[O:16]1[CH2:22][C@@H:21]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C>>[CH3:8][N:7]1[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[N:3]=[C:2]1[N:19]1[CH2:20][C@H:21]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH2:22][O:16][CH2:17][CH2:18]1 | null | US09108957B2_0144 | 2,015 | CCN(CC)CC.Cl[c:3]1[n:2]([CH3:1])[c:28](=[O:29])[cH:27][c:20](-[c:21]2[cH:22][cH:23][n:24][cH:25][n:26]2)[n:19]1.[NH:4]1[CH2:5][CH2:6][O:7][CH2:8][C@@H:9]([c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]2)[CH2:18]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][O:7][CH2:8][C@@H:9]([c:10]3[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]3)[CH2:18]2)[n:19][c:20](-[c:21]2[cH:22][cH:23][n:24][cH:25][n:26]2)[cH:27][c:28]1=[O:29] | 0.949205 | CCN(CC)CC.Cn1c(Cl)nc(-c2ccncn2)cc1=O.N#Cc1ccc([C@H]2CNCCOC2)cc1>>Cn1c(N2CCOC[C@@H](c3ccc(C#N)cc3)C2)nc(-c2ccncn2)cc1=O | CCN(CC)CC.Cn1c(Cl)nc(-c2ccncn2)cc1=O.N#Cc1ccc([C@H]2CNCCOC2)cc1>>Cn1c(N2CCOC[C@@H](c3ccc(C#N)cc3)C2)nc(-c2ccncn2)cc1=O | US09108957B2_0144grants | 173d3bef75317d98212421cf21a0decd14f0f1c1d6a2e77c73801278 | CCN(CC)CC.Cl[c:3]1[n:2]([CH3:1])[c:28](=[O:29])[cH:27][c:20](-[c:21]2[cH:22][cH:23][n:24][cH:25][n:26]2)[n:19]1.[NH:4]1[CH2:5][CH2:6][O:7][CH2:8][C@@H:9]([c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]2)[CH2:18]1 | [CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][O:7][CH2:8][C@@H:9]([c:10]3[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]3)[CH2:18]2)[n:19][c:20](-[c:21]2[cH:22][cH:23][n:24][cH:25][n:26]2)[cH:27][c:28]1=[O:29] | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | b57905a5bce8517a4e40b0e20794e889407f66a0ae3d7a09e7fbb00e | 1 | 1 | CCN(CC)CC | 36 |
212,103 | 715,395 | 1,178,061 | [CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]([C:19]1[S:23][N:22]=[CH:21][N:20]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13](F)=[CH:12][C:11]=1[F:18])(=[O:9])=[O:8].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C:38]2[N:42]([CH:43]3[CH2:46][N:45]([CH:47]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[CH2:44]3)[N:41]=[CH:40][CH:39]=2)[CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:13]2[C:14]([F:16])=[CH:15][C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:3]=3[O:2][CH3:1])[C:19]3[S:23][N:22]=[CH:21][N:20]=3)(=[O:9])=[O:8])=[C:11]([F:18])[CH:12]=2)=[C:33]([C:38]2[N:42]([CH:43]3[CH2:46][N:45]([CH:47]([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[CH2:44]3)[N:41]=[CH:40][CH:39]=2)[CH:32]=1 | |f:2.3.4| | US08153814B2_1183 | 2,012 | CS(C)=O.F[c:21]1[c:19]([F:20])[cH:18][c:17]([S:14]([N:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:58][c:55]2[O:56][CH3:57])[c:9]2[n:10][cH:11][n:12][s:13]2)(=[O:15])=[O:16])[c:53]([F:54])[cH:52]1.O=C([O-])[O-].[K+].[K+].[OH:22][c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]1-[c:30]1[cH:31][cH:32][n:33][n:34]1[CH:35]1[CH2:36][N:37]([CH:38]([c:39]2[cH:40][cH:41][cH:42][cH:43][cH:44]2)[c:45]2[cH:46][cH:47][cH:48][cH:49][cH:50]2)[CH2:51]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([c:9]2[n:10][cH:11][n:12][s:13]2)[S:14](=[O:15])(=[O:16])[c:17]2[cH:18][c:19]([F:20])[c:21]([O:22][c:23]3[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]3-[c:30]3[cH:31][cH:32][n:33][n:34]3[CH:35]3[CH2:36][N:37]([CH:38]([c:39]4[cH:40][cH:41][cH:42][cH:43][cH:44]4)[c:45]4[cH:46][cH:47][cH:48][cH:49][cH:50]4)[CH2:51]3)[cH:52][c:53]2[F:54])[c:55]([O:56][CH3:57])[cH:58]1 | 0.248735 | COc1ccc(CN(c2ncns2)S(=O)(=O)c2cc(F)c(F)cc2F)c(OC)c1.CS(C)=O.O=C([O-])[O-]~[K+]~[K+].Oc1ccc(Cl)cc1-c1ccnn1C1CN(C(c2ccccc2)c2ccccc2)C1>>COc1ccc(CN(c2ncns2)S(=O)(=O)c2cc(F)c(Oc3ccc(Cl)cc3-c3ccnn3C3CN(C(c4ccccc4)c4ccccc4)C3)cc2F)c(OC)c1 | COc1ccc(CN(c2ncns2)S(=O)(=O)c2cc(F)c(F)cc2F)c(OC)c1.CS(C)=O.O=C([O-])[O-].Oc1ccc(Cl)cc1-c1ccnn1C1CN(C(c2ccccc2)c2ccccc2)C1.[K+].[K+]>>COc1ccc(CN(c2ncns2)S(=O)(=O)c2cc(F)c(Oc3ccc(Cl)cc3-c3ccnn3C3CN(C(c4ccccc4)c4ccccc4)C3)cc2F)c(OC)c1 | US08153814B2_1183grants | e997902982731640eda2338dc5a1aab602fd83e5f18f771c0c5cd1e2 | CS(C)=O.F[c:21]1[c:19]([F:20])[cH:18][c:17]([S:14]([N:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:58][c:55]2[O:56][CH3:57])[c:9]2[n:10][cH:11][n:12][s:13]2)(=[O:15])=[O:16])[c:53]([F:54])[cH:52]1.O=C([O-])[O-].[K+].[K+].[OH:22][c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]1-[c:30]1[cH:31][cH:32][n:33][n:34]1[CH:35]1[CH2:36][N:37]([CH:38]([c:39]2[cH:40][cH:41][cH:42][cH:43][cH:44]2)[c:45]2[cH:46][cH:47][cH:48][cH:49][cH:50]2)[CH2:51]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([c:9]2[n:10][cH:11][n:12][s:13]2)[S:14](=[O:15])(=[O:16])[c:17]2[cH:18][c:19]([F:20])[c:21]([O:22][c:23]3[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]3-[c:30]3[cH:31][cH:32][n:33][n:34]3[CH:35]3[CH2:36][N:37]([CH:38]([c:39]4[cH:40][cH:41][cH:42][cH:43][cH:44]4)[c:45]4[cH:46][cH:47][cH:48][cH:49][cH:50]4)[CH2:51]3)[cH:52][c:53]2[F:54])[c:55]([O:56][CH3:57])[cH:58]1 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[O;H0;D2;+0:4]-[c:5])>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]).([OH;D1;+0:4]-[c:5]) | 699454af32c1dcb65df79638d1d0d44f5818d2b11a2a1ca9e88190c9 | 0.5 | 2 | CS(C)=O.O=C([O-])[O-].[K+].[K+] | 564 |
145,923 | 523,369 | 877,234 | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:10]=1)[CH2:7][NH:8][CH3:9].CCN(CC)CC.[C:35](O[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>C(Cl)Cl.[OH-].[Na+]>[C:38]([O:37][C:35](=[O:36])[N:8]([CH2:7][C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[CH3:9])([CH3:39])([CH3:40])[CH3:41] | |f:4.5| | US07479493B2_0132 | 2,009 | CC(C)(C)OC(=O)O[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26].CCN(CC)CC.ClCCl.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1.[Na+].[OH-]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1)[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26] | 0.323295 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCN(CC)CC.CNCc1cc(Br)ccc1Oc1ccc(Cl)c(Cl)c1.ClCCl.[Na+]~[OH-]>>CN(Cc1cc(Br)ccc1Oc1ccc(Cl)c(Cl)c1)C(=O)OC(C)(C)C | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCN(CC)CC.CNCc1cc(Br)ccc1Oc1ccc(Cl)c(Cl)c1.ClCCl.[Na+].[OH-]>>CN(Cc1cc(Br)ccc1Oc1ccc(Cl)c(Cl)c1)C(=O)OC(C)(C)C | US07479493B2_0132grants | ce693ecdd0b274a093c1d2fbe8fb47bf4645201485af886d162f82bd | CC(C)(C)OC(=O)O[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26].CCN(CC)CC.ClCCl.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1.[Na+].[OH-] | [CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1)[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26] | ([C;D1;H3:8]-[N;H0;D3;+0:9](-[C:10]-[c:11]1:[c:12]:[c:13]:[c:14]:[c:15]:[c:16]:1)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])>>(C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7]).([C;D1;H3:8]-[NH;D2;+0:9]-[C:10]-[c:11]1:[c:12]:[c:13]:[c:14]:[c:15]:[c:16]:1) | f0314fa92a644df99bc06279ded7328315bdecbd6db57d426bb7839b | 1 | 1 | CCN(CC)CC.ClCCl.[Na+].[OH-] | 867 |
97,534 | 377,602 | 646,445 | [I:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([I:11])[C:5]([N+:12]([O-])=O)=[C:4]([I:15])[C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.[Sn].Cl>>[I:1][C:2]1[C:7]([NH2:8])=[C:6]([I:11])[C:5]([NH2:12])=[C:4]([I:15])[C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1 | |^3:22| | US06723746B2_ | 2,004 | Cl.O=[N+:10]([O-])[c:9]1[c:7]([I:8])[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]2)[c:15]([I:16])[c:13]([N+:14](=O)[O-])[c:11]1[I:12].[Sn]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([I:8])[c:9]([NH2:10])[c:11]([I:12])[c:13]([NH2:14])[c:15]2[I:16])[cH:17][cH:18]1 | 0.779771 | Cc1ccc(-c2c(I)c([N+](=O)[O-])c(I)c([N+](=O)[O-])c2I)cc1.Cl.[Sn]>>Cc1ccc(-c2c(I)c(N)c(I)c(N)c2I)cc1 | Cc1ccc(-c2c(I)c([N+](=O)[O-])c(I)c([N+](=O)[O-])c2I)cc1.Cl.[Sn]>>Cc1ccc(-c2c(I)c(N)c(I)c(N)c2I)cc1 | US06723746B2_grants | 0f26aa55b5d39b103b583bb9e8e0517a6438fe06697b1f9acd327bb0 | Cl.O=[N+:10]([O-])[c:9]1[c:7]([I:8])[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]2)[c:15]([I:16])[c:13]([N+:14](=O)[O-])[c:11]1[I:12].[Sn] | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([I:8])[c:9]([NH2:10])[c:11]([I:12])[c:13]([NH2:14])[c:15]2[I:16])[cH:17][cH:18]1 | ([NH2;D1;+0:1]-[c:2].[NH2;D1;+0:3]-[c:4])>>(O=[N+;H0;D3:1](-[O-])-[c:2].O=[N+;H0;D3:3](-[O-])-[c:4]) | b52918586402c60354cd21a5a3d4340b19906d8e64b7776a6c1f9378 | 0 | 1 | Cl.[Sn] | 204 |
294,924 | 960,358 | 1,615,395 | [C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].S(Cl)(Cl)=O.[CH3:17]N(C)C=O.O>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:17])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2] | null | US09029531B2_0730 | 2,015 | CN(C)C=O.O.O=S(Cl)Cl.O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13]1.[CH3:1][OH:2]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13]1 | 0.678629 | CN(C)C=O.CO.N#Cc1cccc(CC(=O)O)c1.O.O=S(Cl)Cl>>COC(=O)Cc1cccc(C#N)c1 | CN(C)C=O.CO.N#Cc1cccc(CC(=O)O)c1.O.O=S(Cl)Cl>>COC(=O)Cc1cccc(C#N)c1 | US09029531B2_0730grants | 63a616ffb67e250bd06a25fed9d9f5b8f3c1eab574d4d3cccb1ff7d6 | CN(C)C=O.O.O=S(Cl)Cl.O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13]1.[CH3:1][OH:2] | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:5]-[C;D1;H3:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C;D1;H3:4]-[OH;D1;+0:5]) | a6871142fd86a88cf89e8dce15586c0c2325bd32f2c5592778c4dcb1 | 1 | 1 | CN(C)C=O.O.O=S(Cl)Cl | 17 |
220,603 | 740,782 | 1,220,493 | [CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-])=O)=[CH:10][C:5]=2[N:4]=[C:3]1[C:14]([F:17])([F:16])[F:15]>CO.[Pd]>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[N:4]=[C:3]1[C:14]([F:16])([F:15])[F:17] | null | US08247556B2_0696 | 2,012 | CO.O=[N+:12]([O-])[c:11]1[cH:10][c:9]2[n:8][c:3]([C:4]([F:5])([F:6])[F:7])[n:2]([CH3:1])[c:15]2[cH:14][cH:13]1.[Pd]>>[CH3:1][n:2]1[c:3]([C:4]([F:5])([F:6])[F:7])[n:8][c:9]2[cH:10][c:11]([NH2:12])[cH:13][cH:14][c:15]12 | 0.327135 | CO.Cn1c(C(F)(F)F)nc2cc([N+](=O)[O-])ccc21.[Pd]>>Cn1c(C(F)(F)F)nc2cc(N)ccc21 | CO.Cn1c(C(F)(F)F)nc2cc([N+](=O)[O-])ccc21.[Pd]>>Cn1c(C(F)(F)F)nc2cc(N)ccc21 | US08247556B2_0696grants | 34893e444c8616d5a6854287338d0aac1b3ad3a182e9cc1c95eeb770 | CO.O=[N+:12]([O-])[c:11]1[cH:10][c:9]2[n:8][c:3]([C:4]([F:5])([F:6])[F:7])[n:2]([CH3:1])[c:15]2[cH:14][cH:13]1.[Pd] | [CH3:1][n:2]1[c:3]([C:4]([F:5])([F:6])[F:7])[n:8][c:9]2[cH:10][c:11]([NH2:12])[cH:13][cH:14][c:15]12 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pd] | 1 |
136,380 | 494,379 | 833,013 | [F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1.[C:23](Cl)(=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)(O)[O-].[Na+]>O1CCCC1.N1C=CC=CC=1>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[O:20][C:23](=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1 | |f:2.3| | US07361645B2_0128 | 2,008 | C1CCOC1.Cl[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8].O=C([O-])O.[Na+].[OH:9][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C@H:14]3[C@H:15]([C@@H:16]([F:17])[CH2:18][C@:19]12[CH3:20])[C@H:21]1[CH2:22][CH2:23][C:24](=[O:25])[CH:26]=[C:27]1[CH2:28][C@H:29]3[CH3:30].c1ccncc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[O:9][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C@H:14]3[C@H:15]([C@@H:16]([F:17])[CH2:18][C@:19]12[CH3:20])[C@H:21]1[CH2:22][CH2:23][C:24](=[O:25])[CH:26]=[C:27]1[CH2:28][C@H:29]3[CH3:30] | 0.9004 | C1CCOC1.CCCCCCC(=O)Cl.C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@H](O)[C@@]1(C)C[C@@H]2F.O=C([O-])O~[Na+].c1ccncc1>>CCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3[C@H](C)CC4=CC(=O)CC[C@@H]4[C@H]3[C@@H](F)C[C@]12C | C1CCOC1.CCCCCCC(=O)Cl.C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@H](O)[C@@]1(C)C[C@@H]2F.O=C([O-])O.[Na+].c1ccncc1>>CCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3[C@H](C)CC4=CC(=O)CC[C@@H]4[C@H]3[C@@H](F)C[C@]12C | US07361645B2_0128grants | dc1a62883fa60ba94af7d1cc673a06b2ae9161244d2a70fb5bafb4fd | C1CCOC1.Cl[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8].O=C([O-])O.[Na+].[OH:9][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C@H:14]3[C@H:15]([C@@H:16]([F:17])[CH2:18][C@:19]12[CH3:20])[C@H:21]1[CH2:22][CH2:23][C:24](=[O:25])[CH:26]=[C:27]1[CH2:28][C@H:29]3[CH3:30].c1ccncc1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[O:9][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C@H:14]3[C@H:15]([C@@H:16]([F:17])[CH2:18][C@:19]12[CH3:20])[C@H:21]1[CH2:22][CH2:23][C:24](=[O:25])[CH:26]=[C:27]1[CH2:28][C@H:29]3[CH3:30] | ([C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[OH;D1;+0:5]) | dd95e42df91c7014b8bb61b2fcc1694968b310b2018cb51dbcc5f881 | 1 | 1 | C1CCOC1.O=C([O-])O.[Na+].c1ccncc1 | 126 |
241,219 | 803,731 | 1,331,037 | [CH2:1]([N:3]([CH2:33][CH3:34])[C:4](=[O:32])[CH:5]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=1)[C:6]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])=[O:7])[CH3:2].C(OCC)(=O)C>C(O)C.[Pd]>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH:5]([C:6]([NH:8][S:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)(=[O:11])=[O:10])=[O:7])[C:4]([N:3]([CH2:1][CH3:2])[CH2:33][CH3:34])=[O:32])=[CH:24][CH:25]=1 | null | US08461209B2_0307 | 2,013 | CCO.CCOC(C)=O.O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]([CH2:9][CH:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[C:17](=[O:18])[NH:19][S:20](=[O:21])(=[O:22])[c:23]2[cH:24][cH:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]3[cH:32]2)[cH:16][cH:15]1.[Pd]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]1)[C:17](=[O:18])[NH:19][S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[cH:32]1 | 0.43327 | CCN(CC)C(=O)C(Cc1ccc([N+](=O)[O-])cc1)C(=O)NS(=O)(=O)c1ccc2ccccc2c1.CCO.CCOC(C)=O.[Pd]>>CCN(CC)C(=O)C(Cc1ccc(N)cc1)C(=O)NS(=O)(=O)c1ccc2ccccc2c1 | CCN(CC)C(=O)C(Cc1ccc([N+](=O)[O-])cc1)C(=O)NS(=O)(=O)c1ccc2ccccc2c1.CCO.CCOC(C)=O.[Pd]>>CCN(CC)C(=O)C(Cc1ccc(N)cc1)C(=O)NS(=O)(=O)c1ccc2ccccc2c1 | US08461209B2_0307grants | 15f574fea0de3389cb4977dde69dbd008ad407d4e8dc628c94abd77c | CCO.CCOC(C)=O.O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]([CH2:9][CH:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[C:17](=[O:18])[NH:19][S:20](=[O:21])(=[O:22])[c:23]2[cH:24][cH:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]3[cH:32]2)[cH:16][cH:15]1.[Pd] | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]1)[C:17](=[O:18])[NH:19][S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[cH:32]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.CCOC(C)=O.[Pd] | 1 |
198,088 | 678,098 | 1,119,576 | [C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>CN(C(OC)OC)C>[CH3:8][N:10]([CH3:12])/[CH:11]=[CH:2]/[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([N:10]([CH3:11])[CH3:12])=[O:9])=[CH:6][CH:5]=1)=[O:3] | null | US08034940B2_0782 | 2,011 | CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[CH3:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[cH:17][cH:18]1>>[CH3:1][N:2]([CH3:3])/[CH:4]=[CH:5]/[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[cH:17][cH:18]1 | 0.322869 | CC(=O)c1ccc(C(=O)N(C)C)cc1.COC(OC)N(C)C>>CN(C)/C=C/C(=O)c1ccc(C(=O)N(C)C)cc1 | CC(=O)c1ccc(C(=O)N(C)C)cc1.COC(OC)N(C)C>>CN(C)/C=C/C(=O)c1ccc(C(=O)N(C)C)cc1 | US08034940B2_0782grants | a33eda2362582d5a7623f03e3889df3375a31dee3431d2c7df917ffd | CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[CH3:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[cH:17][cH:18]1 | [CH3:1][N:2]([CH3:3])/[CH:4]=[CH:5]/[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[cH:17][cH:18]1 | ([#7:2]/[CH;D2;+0:1]=[CH;D2;+0:3]/[C:4]=[O;D1;H0:5])>>(C-O-[CH;D3;+0:1](-[#7:2])-O-C).([CH3;D1;+0:3]-[C:4]=[O;D1;H0:5]) | 9dca329e006dfe13f815a162d5d29103ed84ffa590942bc45e34d517 | 1 | 1 | null | 898 |
437,797 | 1,892,948 | null | [Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:15]([OH:17])=O)=[CH:5][N:6]2[CH:11]1[CH2:14][O:13][CH2:12]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:43][CH2:44][C:45]1([OH:53])[CH2:50][CH2:49][C:48]([F:52])([F:51])[CH2:47][CH2:46]1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:15]([NH:43][CH2:44][C:45]1([OH:53])[CH2:46][CH2:47][C:48]([F:52])([F:51])[CH2:49][CH2:50]1)=[O:17])=[CH:5][N:6]2[CH:11]1[CH2:12][O:13][CH2:14]1 | |f:1.2,3.4| | US20160168090A1_0582 | 2,016 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:2](=[O:1])[c:14]1[cH:15][n:16]([CH:17]2[CH2:18][O:19][CH2:20]2)[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[c:27]12.[NH2:3][CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][C:9]([F:10])([F:11])[CH2:12][CH2:13]1>>[O:1]=[C:2]([NH:3][CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][C:9]([F:10])([F:11])[CH2:12][CH2:13]1)[c:14]1[cH:15][n:16]([CH:17]2[CH2:18][O:19][CH2:20]2)[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[c:27]12 | 0.433766 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.Cl~NCC1(O)CCC(F)(F)CC1.O=C(O)c1cn(C2COC2)c2cccc(Cl)c12>>O=C(NCC1(O)CCC(F)(F)CC1)c1cn(C2COC2)c2cccc(Cl)c12 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.NCC1(O)CCC(F)(F)CC1.O=C(O)c1cn(C2COC2)c2cccc(Cl)c12>>O=C(NCC1(O)CCC(F)(F)CC1)c1cn(C2COC2)c2cccc(Cl)c12 | US20160168090A1_0582apps | 3c3716b262aa804eca4d2cf5cd007b57fb6011215c2e500637fdf6cd | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:2](=[O:1])[c:14]1[cH:15][n:16]([CH:17]2[CH2:18][O:19][CH2:20]2)[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[c:27]12.[NH2:3][CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][C:9]([F:10])([F:11])[CH2:12][CH2:13]1 | [O:1]=[C:2]([NH:3][CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][C:9]([F:10])([F:11])[CH2:12][CH2:13]1)[c:14]1[cH:15][n:16]([CH:17]2[CH2:18][O:19][CH2:20]2)[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[c:27]12 | ([#7;a:5]:[c:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[c:4]:[#7;a:5]).([C:6]-[NH2;D1;+0:7]) | c8d3e8be644ca37fe3075935d6d9f9515443e1dc5a5fca512a1988ac | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F | 674 |
365,385 | 686,597 | null | [C:1]([C:3]1[C:4]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:5][C:6]([CH3:23])=[C:7]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[C:8]([O:10]C(C)(C)C)=[O:9])#[N:2]>FC(F)(F)C(O)=O>[C:1]([C:3]1[C:4]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:5][C:6]([CH3:23])=[C:7]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[C:8]([OH:10])=[O:9])#[N:2] | null | US20090088419A1_0348 | 2,009 | CC(C)(C)[O:22][C:20]([c:19]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]2)[c:7]([C:8]#[N:9])[c:10]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][c:17]1[CH3:18])=[O:21].O=C(O)C(F)(F)F>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([C:8]#[N:9])[c:10]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][c:17]([CH3:18])[c:19]2[C:20](=[O:21])[OH:22])[cH:23][cH:24]1 | 0.402175 | Cc1ccc(-c2c(C#N)c(CC(C)(C)C)nc(C)c2C(=O)OC(C)(C)C)cc1.O=C(O)C(F)(F)F>>Cc1ccc(-c2c(C#N)c(CC(C)(C)C)nc(C)c2C(=O)O)cc1 | Cc1ccc(-c2c(C#N)c(CC(C)(C)C)nc(C)c2C(=O)OC(C)(C)C)cc1.O=C(O)C(F)(F)F>>Cc1ccc(-c2c(C#N)c(CC(C)(C)C)nc(C)c2C(=O)O)cc1 | US20090088419A1_0348apps | 557df568177114ea744545cd66befca9b41c8f0f0cdf59bdf0ada102 | CC(C)(C)[O:22][C:20]([c:19]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]2)[c:7]([C:8]#[N:9])[c:10]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][c:17]1[CH3:18])=[O:21].O=C(O)C(F)(F)F | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([C:8]#[N:9])[c:10]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][c:17]([CH3:18])[c:19]2[C:20](=[O:21])[OH:22])[cH:23][cH:24]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | fe3c3299a6a9df7b3c1701ce67d84c72d884241ba1e583122581dc1b | 1 | 1 | O=C(O)C(F)(F)F | 569 |
388,433 | 1,089,635 | null | [CH3:1][O:2][C:3]1[C:8]2[NH:9][C:10]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)=[N:11][C:7]=2[C:6]([C:17]([OH:19])=O)=[CH:5][CH:4]=1.[NH2:20][CH2:21][CH2:22][NH:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([S:24]([NH:23][CH2:22][CH2:21][NH:20][C:17]([C:6]2[C:7]3[N:11]=[C:10]([C:12]4[S:13][CH:14]=[CH:15][CH:16]=4)[NH:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:19])(=[O:25])=[O:26])=[CH:32][CH:31]=1 | null | US20110190351A1_0260 | 2,011 | O[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:32]2[c:23]1[n:24][c:25](-[c:26]1[cH:27][cH:28][cH:29][s:30]1)[nH:31]2)=[O:8].[NH2:9][CH2:10][CH2:11][NH:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][CH2:11][NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[c:23]2[n:24][c:25](-[c:26]3[cH:27][cH:28][cH:29][s:30]3)[nH:31][c:32]12 | 0.506425 | COc1ccc(C(=O)O)c2nc(-c3cccs3)[nH]c12.NCCNS(=O)(=O)c1ccc(Cl)cc1>>COc1ccc(C(=O)NCCNS(=O)(=O)c2ccc(Cl)cc2)c2nc(-c3cccs3)[nH]c12 | COc1ccc(C(=O)O)c2nc(-c3cccs3)[nH]c12.NCCNS(=O)(=O)c1ccc(Cl)cc1>>COc1ccc(C(=O)NCCNS(=O)(=O)c2ccc(Cl)cc2)c2nc(-c3cccs3)[nH]c12 | US20110190351A1_0260apps | 878d17f2ceb07d16a6130a9fd060bf49614352e17b36e601faa7f1c2 | O[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:32]2[c:23]1[n:24][c:25](-[c:26]1[cH:27][cH:28][cH:29][s:30]1)[nH:31]2)=[O:8].[NH2:9][CH2:10][CH2:11][NH:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][CH2:11][NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[c:23]2[n:24][c:25](-[c:26]3[cH:27][cH:28][cH:29][s:30]3)[nH:31][c:32]12 | ([#7;a:5]:[c:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[c:4]:[#7;a:5]).([C:6]-[NH2;D1;+0:7]) | c8d3e8be644ca37fe3075935d6d9f9515443e1dc5a5fca512a1988ac | 1 | 1 | null | 674 |
238,266 | 795,188 | 1,316,205 | [C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:30][NH:31][O:32][CH3:33]>C1COCC1.CCOC(C)=O>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[N:31]([O:32][CH3:33])[CH3:30])[CH2:12][CH2:13]1)=[O:2])([CH3:5])([CH3:6])[CH3:7] | |f:2.3| | US08431695B2_1369 | 2,013 | C1CCOC1.CCOC(C)=O.Cl.O=C(n1ccnc1)n1ccnc1.O[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1.[CH3:1][O:2][NH:3][CH3:4]>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | 0.23405 | C1CCOC1.CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1.CCOC(C)=O.CNOC~Cl.O=C(n1ccnc1)n1ccnc1>>CON(C)C(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | C1CCOC1.CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1.CCOC(C)=O.CNOC.Cl.O=C(n1ccnc1)n1ccnc1>>CON(C)C(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | US08431695B2_1369grants | 6cde77efeb6d89490f706afff9a581fd8ba1f0f183094197b19d04b1 | C1CCOC1.CCOC(C)=O.Cl.O=C(n1ccnc1)n1ccnc1.O[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1.[CH3:1][O:2][NH:3][CH3:4] | [CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | ([#8:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#8:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | e12e17c16fdd82cb71a098517c68119425dd3668f93c08def7cb5247 | 1 | 1 | C1CCOC1.CCOC(C)=O.Cl.O=C(n1ccnc1)n1ccnc1 | 54 |
168,062 | 590,643 | 979,601 | Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]([CH3:13])([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)[CH3:6].[CH:15](O)=O.C=O>[OH-].[Na+]>[CH3:2][O:3][C:4](=[O:14])[C:5]([CH3:6])([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH3:15])[CH2:8]1)[CH3:13] | |f:0.1,4.5| | US07718675B2_0322 | 2,010 | Cl.O=CO.O=[CH2:13].[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH:8]1[CH2:9][CH2:10][CH2:11][NH:12][CH2:14]1.[Na+].[OH-]>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH:8]1[CH2:9][CH2:10][CH2:11][N:12]([CH3:13])[CH2:14]1 | 0.625919 | C=O.COC(=O)C(C)(C)C1CCCNC1~Cl.O=CO.[Na+]~[OH-]>>COC(=O)C(C)(C)C1CCCN(C)C1 | C=O.COC(=O)C(C)(C)C1CCCNC1.Cl.O=CO.[Na+].[OH-]>>COC(=O)C(C)(C)C1CCCN(C)C1 | US07718675B2_0322grants | 4166a4c0efe62608398154ea8f81b2186638e6d3c3c3a1ddccf62d97 | Cl.O=CO.O=[CH2:13].[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH:8]1[CH2:9][CH2:10][CH2:11][NH:12][CH2:14]1.[Na+].[OH-] | [CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH:8]1[CH2:9][CH2:10][CH2:11][N:12]([CH3:13])[CH2:14]1 | ([C:2]-[N;H0;D3;+0:3](-[C:4])-[CH3;D1;+0:1])>>(O=[CH2;D1;+0:1]).([C:2]-[NH;D2;+0:3]-[C:4]) | fb44fedb5e2cc8d07bdd0b6fb6f327584934b65e8fb8e97e63bb7532 | 1 | 1 | Cl.O=CO.[Na+].[OH-] | 217 |
308,075 | 1,001,516 | 1,693,444 | [CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[CH:21]1([CH2:24][NH:25][CH2:26][C:27]2[NH:28][C:29](=[O:38])[C:30]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C:31]=3[N:32]=2)[CH2:23][CH2:22]1>>[CH:21]1([CH2:24][N:25]([CH2:26][C:27]2[NH:28][C:29](=[O:38])[C:30]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C:31]=3[N:32]=2)[C:16](=[O:18])[CH2:15][N:12]2[CH2:11][CH2:10][CH:9]([C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)[CH2:23][CH2:22]1 | null | US09181266B2_0602 | 2,015 | O[C:14]([CH2:13][N:12]1[CH2:11][CH2:10][CH:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]2)=[O:8])[CH2:35][CH2:34]1)=[O:15].[NH:16]([CH2:17][c:18]1[n:19][c:20]2[c:21]([c:22](=[O:23])[nH:24]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:30][CH:31]1[CH2:32][CH2:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][N:12]([CH2:13][C:14](=[O:15])[N:16]([CH2:17][c:18]3[n:19][c:20]4[c:21]([c:22](=[O:23])[nH:24]3)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)[CH2:30][CH:31]3[CH2:32][CH2:33]3)[CH2:34][CH2:35]2)[cH:36][cH:37]1 | 0.86451 | COc1ccc(C(=O)C2CCN(CC(=O)O)CC2)cc1.O=c1[nH]c(CNCC2CC2)nc2c1CCCCC2>>COc1ccc(C(=O)C2CCN(CC(=O)N(Cc3nc4c(c(=O)[nH]3)CCCCC4)CC3CC3)CC2)cc1 | COc1ccc(C(=O)C2CCN(CC(=O)O)CC2)cc1.O=c1[nH]c(CNCC2CC2)nc2c1CCCCC2>>COc1ccc(C(=O)C2CCN(CC(=O)N(Cc3nc4c(c(=O)[nH]3)CCCCC4)CC3CC3)CC2)cc1 | US09181266B2_0602grants | 9d3064643d5e7279a15b0398dd7756ca577225af864ebe11638bdcd8 | O[C:14]([CH2:13][N:12]1[CH2:11][CH2:10][CH:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]2)=[O:8])[CH2:35][CH2:34]1)=[O:15].[NH:16]([CH2:17][c:18]1[n:19][c:20]2[c:21]([c:22](=[O:23])[nH:24]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:30][CH:31]1[CH2:32][CH2:33]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][N:12]([CH2:13][C:14](=[O:15])[N:16]([CH2:17][c:18]3[n:19][c:20]4[c:21]([c:22](=[O:23])[nH:24]3)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)[CH2:30][CH:31]3[CH2:32][CH2:33]3)[CH2:34][CH2:35]2)[cH:36][cH:37]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | null | 146 |
9,384 | 47,752 | 77,069 | [N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10]([CH2:12][C:13]([OH:15])=O)=[O:11].[NH2:16][CH:17]1[C:35](=[O:36])[N:19]2[C:20]([C:32]([OH:34])=[O:33])=[C:21]([CH2:24][S:25][C:26]3[S:30][C:29]([CH3:31])=[N:28][N:27]=3)[CH2:22][S:23][C@H:18]12>>[N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:1][C:2]=1[S:10]([CH2:12][C:13]([NH:16][CH:17]1[C:35](=[O:36])[N:19]2[C:20]([C:32]([OH:34])=[O:33])=[C:21]([CH2:24][S:25][C:26]3[S:30][C:29]([CH3:31])=[N:28][N:27]=3)[CH2:22][S:23][C@H:18]12)=[O:15])=[O:11] | null | US04245107_ | 1,981 | O[C:18](=[O:19])[CH2:20][S:21](=[O:22])[c:23]1[n:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[nH:31]1.[CH3:1][c:2]1[n:3][n:4][c:5]([S:6][CH2:7][C:8]2=[C:9]([C:10](=[O:11])[OH:12])[N:13]3[C:14](=[O:15])[CH:16]([NH2:17])[C@H:32]3[S:33][CH2:34]2)[s:35]1>>[CH3:1][c:2]1[n:3][n:4][c:5]([S:6][CH2:7][C:8]2=[C:9]([C:10](=[O:11])[OH:12])[N:13]3[C:14](=[O:15])[CH:16]([NH:17][C:18](=[O:19])[CH2:20][S:21](=[O:22])[c:23]4[n:24][c:25]5[cH:26][cH:27][cH:28][cH:29][c:30]5[nH:31]4)[C@H:32]3[S:33][CH2:34]2)[s:35]1 | 0.832073 | Cc1nnc(SCC2=C(C(=O)O)N3C(=O)C(N)[C@H]3SC2)s1.O=C(O)CS(=O)c1nc2ccccc2[nH]1>>Cc1nnc(SCC2=C(C(=O)O)N3C(=O)C(NC(=O)CS(=O)c4nc5ccccc5[nH]4)[C@H]3SC2)s1 | Cc1nnc(SCC2=C(C(=O)O)N3C(=O)C(N)[C@H]3SC2)s1.O=C(O)CS(=O)c1nc2ccccc2[nH]1>>Cc1nnc(SCC2=C(C(=O)O)N3C(=O)C(NC(=O)CS(=O)c4nc5ccccc5[nH]4)[C@H]3SC2)s1 | US04245107_grants | b89a0d00bed11fa9022eb4578188fb290c7176027cd69aa983ef0875 | O[C:18](=[O:19])[CH2:20][S:21](=[O:22])[c:23]1[n:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[nH:31]1.[CH3:1][c:2]1[n:3][n:4][c:5]([S:6][CH2:7][C:8]2=[C:9]([C:10](=[O:11])[OH:12])[N:13]3[C:14](=[O:15])[CH:16]([NH2:17])[C@H:32]3[S:33][CH2:34]2)[s:35]1 | [CH3:1][c:2]1[n:3][n:4][c:5]([S:6][CH2:7][C:8]2=[C:9]([C:10](=[O:11])[OH:12])[N:13]3[C:14](=[O:15])[CH:16]([NH:17][C:18](=[O:19])[CH2:20][S:21](=[O:22])[c:23]4[n:24][c:25]5[cH:26][cH:27][cH:28][cH:29][c:30]5[nH:31]4)[C@H:32]3[S:33][CH2:34]2)[s:35]1 | ([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH2;D1;+0:8]) | 09e961e4c21b1adcf2f8d3b116773699ab5020ae114ca5b853caf10a | 1 | 1 | null | 133 |
264,777 | 871,577 | 1,451,066 | [O:1]1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][NH:10][C:9]3=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Br[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1.CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C>[F:24][C:23]([F:26])([F:25])[C:20]1[CH:21]=[CH:22][C:17]([N:10]2[CH2:11][CH2:12][C:8]3([CH2:14][CH2:15][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:6][CH2:7]3)[C:9]2=[O:13])=[CH:18][CH:19]=1 | |f:3.4.5.6| | US08703807B2_0151 | 2,014 | Br[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]1.CN(C)C=O.CNCCNC.O=P([O-])([O-])[O-].[K+].[K+].[K+].[O:1]=[C:2]1[NH:3][CH2:14][CH2:15][C:16]12[CH2:17][CH2:18][C:19]1([CH2:20][CH2:21]2)[O:22][CH2:23][CH2:24][O:25]1>>[O:1]=[C:2]1[N:3]([c:4]2[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]2)[CH2:14][CH2:15][C:16]12[CH2:17][CH2:18][C:19]1([CH2:20][CH2:21]2)[O:22][CH2:23][CH2:24][O:25]1 | 0.260011 | CN(C)C=O.CNCCNC.FC(F)(F)c1ccc(Br)cc1.O=C1NCCC12CCC1(CC2)OCCO1.O=P([O-])([O-])[O-]~[K+]~[K+]~[K+]>>O=C1N(c2ccc(C(F)(F)F)cc2)CCC12CCC1(CC2)OCCO1 | CN(C)C=O.CNCCNC.FC(F)(F)c1ccc(Br)cc1.O=C1NCCC12CCC1(CC2)OCCO1.O=P([O-])([O-])[O-].[K+].[K+].[K+]>>O=C1N(c2ccc(C(F)(F)F)cc2)CCC12CCC1(CC2)OCCO1 | US08703807B2_0151grants | bd114442b8583fc88bb80c9d5c53867fb0994015f867c6d4bb76d39b | Br[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]1.CN(C)C=O.CNCCNC.O=P([O-])([O-])[O-].[K+].[K+].[K+].[O:1]=[C:2]1[NH:3][CH2:14][CH2:15][C:16]12[CH2:17][CH2:18][C:19]1([CH2:20][CH2:21]2)[O:22][CH2:23][CH2:24][O:25]1 | [O:1]=[C:2]1[N:3]([c:4]2[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]2)[CH2:14][CH2:15][C:16]12[CH2:17][CH2:18][C:19]1([CH2:20][CH2:21]2)[O:22][CH2:23][CH2:24][O:25]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6](-[C:7])=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[NH;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]) | 274fc64807648e92ab4ee19c6473e9c734530b7b5f51c59d812e9906 | 1 | 1 | CN(C)C=O.CNCCNC.O=P([O-])([O-])[O-].[K+].[K+].[K+] | 809 |
238,756 | 796,675 | 1,318,483 | [Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[N+:23]([O-])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)(=O)C.CO.[Fe]>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[NH2:23])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2] | null | US08436178B2_0385 | 2,013 | CC(=O)O.CO.O=[N+:15]([O-])[c:14]1[c:13]([NH:12][CH2:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:23]2[c:18]([n:17][cH:16]1)[cH:19][cH:20][cH:21][cH:22]2.[Fe]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][NH:12][c:13]1[c:14]([NH2:15])[cH:16][n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12 | 0.380473 | CC(=O)O.CC(C)(C)[Si](C)(C)OCCCNc1c([N+](=O)[O-])cnc2ccccc12.CO.[Fe]>>CC(C)(C)[Si](C)(C)OCCCNc1c(N)cnc2ccccc12 | CC(=O)O.CC(C)(C)[Si](C)(C)OCCCNc1c([N+](=O)[O-])cnc2ccccc12.CO.[Fe]>>CC(C)(C)[Si](C)(C)OCCCNc1c(N)cnc2ccccc12 | US08436178B2_0385grants | 2a086b103d777845c49c4b89a464afa34748723aac51a5e90976e372 | CC(=O)O.CO.O=[N+:15]([O-])[c:14]1[c:13]([NH:12][CH2:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:23]2[c:18]([n:17][cH:16]1)[cH:19][cH:20][cH:21][cH:22]2.[Fe] | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][NH:12][c:13]1[c:14]([NH2:15])[cH:16][n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12 | ([#7;a:4]:[c:3]:[c:2]-[NH2;D1;+0:1])>>(O=[N+;H0;D3:1](-[O-])-[c:2]:[c:3]:[#7;a:4]) | e69a09e0931e7bc26f571c5e2ed13b773c90943f0f6753349e287e32 | 1 | 1 | CC(=O)O.CO.[Fe] | 269 |
137,936 | 499,472 | 840,061 | [Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[S:11][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8] | null | US07381736B2_0447 | 2,008 | CCO.O=[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[CH2:16]Br.[Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7]([NH2:8])=[S:17])[cH:18][c:19]1[Cl:20]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][s:17]2)[cH:18][c:19]1[Cl:20] | 0.89168 | CCO.NC(=S)Nc1ccc(Cl)c(Cl)c1.O=C(CBr)c1ccccc1>>Clc1ccc(Nc2nc(-c3ccccc3)cs2)cc1Cl | CCO.NC(=S)Nc1ccc(Cl)c(Cl)c1.O=C(CBr)c1ccccc1>>Clc1ccc(Nc2nc(-c3ccccc3)cs2)cc1Cl | US07381736B2_0447grants | 99447675360d0b48d7f975b6b80879b60801b991d23a5c13e3e28b4e | CCO.O=[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[CH2:16]Br.[Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7]([NH2:8])=[S:17])[cH:18][c:19]1[Cl:20] | [Cl:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][s:17]2)[cH:18][c:19]1[Cl:20] | ([#7:6]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]):[c:5]):[cH;D2;+0:1]:[s;H0;D2;+0:9]:1)>>(Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]):[c:5]).([#7:6]-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[S;H0;D1;+0:9]) | 64963d06c8f8237f33aad050224f9b1e3b455f539326102d0d1b70e9 | 1 | 1 | CCO | 716 |
79,390 | 321,514 | 544,966 | [CH3:1][CH2:2][C@@:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=[CH:20]2)=[O:11]>[Fe].Cl>[CH3:1][CH2:2][C@@:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24]([C:23]([NH2:26])=[CH:22][CH:21]=[CH:20]2)=[CH:25][C:14]=1[CH2:13]3)=[O:11] | null | US06352996B1_ | 2,002 | Cl.O=[N+:21]([O-])[c:20]1[c:19]2[cH:18][c:17]3[c:27]([n:26][c:25]2[cH:24][cH:23][cH:22]1)-[c:12]1[cH:11][c:10]2[c:9]([c:14](=[O:15])[n:13]1[CH2:16]3)[CH2:8][O:7][C:5](=[O:6])[C@@:3]2([CH2:2][CH3:1])[OH:4].[Fe]>>[CH3:1][CH2:2][C@@:3]1([OH:4])[C:5](=[O:6])[O:7][CH2:8][c:9]2[c:10]1[cH:11][c:12]1[n:13]([c:14]2=[O:15])[CH2:16][c:17]2[cH:18][c:19]3[c:20]([NH2:21])[cH:22][cH:23][cH:24][c:25]3[n:26][c:27]2-1 | 0.992933 | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c([N+](=O)[O-])cccc3nc2-1.Cl.[Fe]>>CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(N)cccc3nc2-1 | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c([N+](=O)[O-])cccc3nc2-1.Cl.[Fe]>>CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(N)cccc3nc2-1 | US06352996B1_grants | 6f07cedaa75ad26830efc04b0424ce8347f3ba6903314a15aa003c1a | Cl.O=[N+:21]([O-])[c:20]1[c:19]2[cH:18][c:17]3[c:27]([n:26][c:25]2[cH:24][cH:23][cH:22]1)-[c:12]1[cH:11][c:10]2[c:9]([c:14](=[O:15])[n:13]1[CH2:16]3)[CH2:8][O:7][C:5](=[O:6])[C@@:3]2([CH2:2][CH3:1])[OH:4].[Fe] | [CH3:1][CH2:2][C@@:3]1([OH:4])[C:5](=[O:6])[O:7][CH2:8][c:9]2[c:10]1[cH:11][c:12]1[n:13]([c:14]2=[O:15])[CH2:16][c:17]2[cH:18][c:19]3[c:20]([NH2:21])[cH:22][cH:23][cH:24][c:25]3[n:26][c:27]2-1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | Cl.[Fe] | 1 |
136,389 | 494,424 | 833,085 | [Cl:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[CH:3]=1.[CH:11]1([CH2:14]Br)[CH2:13][CH2:12]1>>[Cl:1][C:2]1[N:7]([CH2:14][CH:11]2[CH2:13][CH2:12]2)[C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[CH:3]=1 | null | US07361660B2_0544 | 2,008 | Br[CH2:9][CH:10]1[CH2:11][CH2:12]1.[CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([Cl:7])[nH:8][c:13]1=[O:14]>>[CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([Cl:7])[n:8]([CH2:9][CH:10]2[CH2:11][CH2:12]2)[c:13]1=[O:14] | 0.95657 | BrCC1CC1.Cn1c(=O)cc(Cl)[nH]c1=O>>Cn1c(=O)cc(Cl)n(CC2CC2)c1=O | BrCC1CC1.Cn1c(=O)cc(Cl)[nH]c1=O>>Cn1c(=O)cc(Cl)n(CC2CC2)c1=O | US07361660B2_0544grants | 06aa12639d187bf011e7372786e4627cf10ca6a7aeba3887d7b89d05 | Br[CH2:9][CH:10]1[CH2:11][CH2:12]1.[CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([Cl:7])[nH:8][c:13]1=[O:14] | [CH3:1][n:2]1[c:3](=[O:4])[cH:5][c:6]([Cl:7])[n:8]([CH2:9][CH:10]2[CH2:11][CH2:12]2)[c:13]1=[O:14] | ([#7;a:3]:[c:4]:[n;H0;D3;+0:5](:[c:6])-[CH2;D2;+0:1]-[C:2])>>(Br-[CH2;D2;+0:1]-[C:2]).([#7;a:3]:[c:4]:[nH;D2;+0:5]:[c:6]) | 3d3a5dfcf98f4af06ca5f681e43e435d0d9351afbe8c8af873fee756 | 1 | 1 | null | 327 |
134,957 | 490,183 | 825,738 | [CH:1]1([CH2:4][O:5][CH2:6][C:7]([OH:9])=O)[CH2:3][CH2:2]1.[NH2:10][C:11]1[N:16]=[N:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[O:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1>>[CH:1]1([CH2:4][O:5][CH2:6][C:7]([NH:10][C:11]2[N:16]=[N:15][C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:23](=[O:24])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])[CH2:21][CH2:22]3)=[CH:13][CH:12]=2)=[O:9])[CH2:2][CH2:3]1 | null | US07335658B2_0371 | 2,008 | O[C:2](=[O:1])[CH2:3][O:4][CH2:5][CH:6]1[CH2:7][CH2:8]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[C:26]([F:27])([F:28])[F:29])[CH2:30][CH2:31]2)[n:32][n:33]1>>[O:1]=[C:2]([CH2:3][O:4][CH2:5][CH:6]1[CH2:7][CH2:8]1)[NH:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[C:26]([F:27])([F:28])[F:29])[CH2:30][CH2:31]2)[n:32][n:33]1 | 0.300048 | Nc1ccc(N2CCN(C(=O)c3ccccc3C(F)(F)F)CC2)nn1.O=C(O)COCC1CC1>>O=C(COCC1CC1)Nc1ccc(N2CCN(C(=O)c3ccccc3C(F)(F)F)CC2)nn1 | Nc1ccc(N2CCN(C(=O)c3ccccc3C(F)(F)F)CC2)nn1.O=C(O)COCC1CC1>>O=C(COCC1CC1)Nc1ccc(N2CCN(C(=O)c3ccccc3C(F)(F)F)CC2)nn1 | US07335658B2_0371grants | ca0cb1e0df0b2be8429afaef7d2b703e31ad5d28b1d3a511660c153d | O[C:2](=[O:1])[CH2:3][O:4][CH2:5][CH:6]1[CH2:7][CH2:8]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[C:26]([F:27])([F:28])[F:29])[CH2:30][CH2:31]2)[n:32][n:33]1 | [O:1]=[C:2]([CH2:3][O:4][CH2:5][CH:6]1[CH2:7][CH2:8]1)[NH:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[C:26]([F:27])([F:28])[F:29])[CH2:30][CH2:31]2)[n:32][n:33]1 | ([#7;a:4]:[#7;a:5]:[c:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7;a:4]:[#7;a:5]:[c:6]-[NH2;D1;+0:7]) | ac6bdb904c3bb8bbc59a5a6dd19b3afc2fd26ad6ace0ef77a514568f | 1 | 1 | null | 795 |
130,812 | 477,702 | 805,727 | [NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[O:4]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[O:4] | null | US07270808B2_0387 | 2,007 | CC(C)(C)OC(=O)[NH:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][C:7](=[O:8])[NH:9][CH2:10][C:11](=[O:12])[OH:13].ClCCl.O=C(O)C(F)(F)F>>[NH2:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][C:7](=[O:8])[NH:9][CH2:10][C:11](=[O:12])[OH:13] | 0.817592 | CC(C)(C)OC(=O)NCC(=O)NCC(=O)NCC(=O)O.ClCCl.O=C(O)C(F)(F)F>>NCC(=O)NCC(=O)NCC(=O)O | CC(C)(C)OC(=O)NCC(=O)NCC(=O)NCC(=O)O.ClCCl.O=C(O)C(F)(F)F>>NCC(=O)NCC(=O)NCC(=O)O | US07270808B2_0387grants | f79ef46031c629a8611b1b18ba964c2e93473ef0a88a0e6d5989a1db | CC(C)(C)OC(=O)[NH:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][C:7](=[O:8])[NH:9][CH2:10][C:11](=[O:12])[OH:13].ClCCl.O=C(O)C(F)(F)F | [NH2:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][C:7](=[O:8])[NH:9][CH2:10][C:11](=[O:12])[OH:13] | ([#7:4]-[C:3](=[O;D1;H0:5])-[C:2]-[NH2;D1;+0:1])>>(C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](-[#7:4])=[O;D1;H0:5]) | 140717369b6c661d32f428907ffcecf2a0f3702c28cc263bfa3ac1c3 | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 431 |
191,731 | 660,240 | 1,092,983 | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[F:10][CH2:11][CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][F:10])=[CH:4][C:3]=1[CH3:9] | |f:5.6| | US07977387B2_0606 | 2,011 | C1CCOC1.CCOC(=O)N=NC(=O)OCC.CCOC(C)=O.O.O[CH2:6][CH2:7][F:8].[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:9][cH:10][c:11]1[Br:12].c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][F:8])[cH:9][cH:10][c:11]1[Br:12] | 0.977617 | C1CCOC1.CCOC(=O)N=NC(=O)OCC.CCOC(C)=O~O.Cc1cc(O)ccc1Br.OCCF.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Cc1cc(OCCF)ccc1Br | C1CCOC1.CCOC(=O)N=NC(=O)OCC.CCOC(C)=O.Cc1cc(O)ccc1Br.O.OCCF.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Cc1cc(OCCF)ccc1Br | US07977387B2_0606grants | f6e5175e0354aec878394dee6efc6dc37f135e39fad97efa77d977d9 | C1CCOC1.CCOC(=O)N=NC(=O)OCC.CCOC(C)=O.O.O[CH2:6][CH2:7][F:8].[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:9][cH:10][c:11]1[Br:12].c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][F:8])[cH:9][cH:10][c:11]1[Br:12] | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(O-[CH2;D2;+0:1]-[C:2]).([OH;D1;+0:3]-[c:4]) | 6b5437625f42979eb76da5582165cd62b5dfeb41d76ac0fbed0bf4a3 | 1 | 1 | C1CCOC1.CCOC(=O)N=NC(=O)OCC.CCOC(C)=O.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 478 |
416,475 | 1,726,669 | null | [C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([C:22](O)=[O:23])=[CH:17][CH:16]=3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:26][C:27]12[CH2:34][CH2:33][C:30]([C:35]([O:37][CH3:38])=[O:36])([CH2:31][CH2:32]1)[CH2:29][CH2:28]2.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([C:22]([NH:26][C:27]24[CH2:28][CH2:29][C:30]([C:35]([O:37][CH3:38])=[O:36])([CH2:33][CH2:34]2)[CH2:31][CH2:32]4)=[O:23])=[CH:17][CH:16]=3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3] | |f:1.2,4.5| | US20150210647A1_1068 | 2,015 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.Cl.ClCCl.F[P-](F)(F)(F)(F)F.O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]2[cH:16][n:17][c:18]([NH:19][C@H:20]3[CH2:21][CH2:22][C@H:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]3)[cH:30][c:31]2[cH:32]1.[CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([NH2:9])([CH2:33][CH2:34]1)[CH2:35][CH2:36]2>>[CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([NH:9][C:10](=[O:11])[c:12]3[cH:13][cH:14][c:15]4[cH:16][n:17][c:18]([NH:19][C@H:20]5[CH2:21][CH2:22][C@H:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]5)[cH:30][c:31]4[cH:32]3)([CH2:33][CH2:34]1)[CH2:35][CH2:36]2 | 0.307107 | CC(C)(C)[C@@H]1CC[C@@H](Nc2cc3cc(C(=O)O)ccc3cn2)CC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.COC(=O)C12CCC(N)(CC1)CC2~Cl.ClCCl>>COC(=O)C12CCC(NC(=O)c3ccc4cnc(N[C@@H]5CC[C@@H](C(C)(C)C)CC5)cc4c3)(CC1)CC2 | CC(C)(C)[C@@H]1CC[C@@H](Nc2cc3cc(C(=O)O)ccc3cn2)CC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.COC(=O)C12CCC(N)(CC1)CC2.Cl.ClCCl.F[P-](F)(F)(F)(F)F>>COC(=O)C12CCC(NC(=O)c3ccc4cnc(N[C@@H]5CC[C@@H](C(C)(C)C)CC5)cc4c3)(CC1)CC2 | US20150210647A1_1068apps | c927f726bfe500ff2595e28cb48d3c280bcbbd3f2f97a74cd3430781 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.Cl.ClCCl.F[P-](F)(F)(F)(F)F.O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]2[cH:16][n:17][c:18]([NH:19][C@H:20]3[CH2:21][CH2:22][C@H:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]3)[cH:30][c:31]2[cH:32]1.[CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([NH2:9])([CH2:33][CH2:34]1)[CH2:35][CH2:36]2 | [CH3:1][O:2][C:3](=[O:4])[C:5]12[CH2:6][CH2:7][C:8]([NH:9][C:10](=[O:11])[c:12]3[cH:13][cH:14][c:15]4[cH:16][n:17][c:18]([NH:19][C@H:20]5[CH2:21][CH2:22][C@H:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]5)[cH:30][c:31]4[cH:32]3)([CH2:33][CH2:34]1)[CH2:35][CH2:36]2 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.Cl.ClCCl.F[P-](F)(F)(F)(F)F | 334 |
160,436 | 567,673 | 946,643 | [OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:26])[CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])(=[O:16])=[O:15])[CH2:6][CH2:5]1.N1C=CC=CC=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].O>ClCCl>[C:33]([O:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10](=[O:26])[CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])(=[O:15])=[O:16])[CH2:8][CH2:9]1)(=[O:35])[CH3:34] | null | US07635684B2_0477 | 2,009 | CC(=O)O[C:2]([CH3:1])=[O:3].ClCCl.O.[OH:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[CH2:13][CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[N+:25](=[O:26])[O-:27])[CH2:28][CH2:29]1.c1ccncc1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[CH2:13][CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[N+:25](=[O:26])[O-:27])[CH2:28][CH2:29]1 | 0.301628 | CC(=O)OC(C)=O.ClCCl.O.O=C(CCNS(=O)(=O)c1ccccc1[N+](=O)[O-])N1CCN(CCO)CC1.c1ccncc1>>CC(=O)OCCN1CCN(C(=O)CCNS(=O)(=O)c2ccccc2[N+](=O)[O-])CC1 | CC(=O)OC(C)=O.ClCCl.O.O=C(CCNS(=O)(=O)c1ccccc1[N+](=O)[O-])N1CCN(CCO)CC1.c1ccncc1>>CC(=O)OCCN1CCN(C(=O)CCNS(=O)(=O)c2ccccc2[N+](=O)[O-])CC1 | US07635684B2_0477grants | 3e0666a71e09b25f171a555702ab8d4f758c0f401910b309154b0dee | CC(=O)O[C:2]([CH3:1])=[O:3].ClCCl.O.[OH:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[CH2:13][CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[N+:25](=[O:26])[O-:27])[CH2:28][CH2:29]1.c1ccncc1 | [CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[CH2:13][CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[N+:25](=[O:26])[O-:27])[CH2:28][CH2:29]1 | ([C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])>>(C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([C:4]-[OH;D1;+0:5]) | fa0bb6d907bde4c9e3e81661aedea03d23c0173afd7eccce9c8dc79b | 1 | 1 | ClCCl.O.c1ccncc1 | 254 |
309,685 | 1,007,199 | 1,703,571 | [Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([CH2:23][CH2:24]Cl)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1.[NH:28]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29]1>CC#N>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([CH2:23][CH2:24][N:28]3[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29]3)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1 | null | US09206191B2_0625 | 2,015 | CC#N.Cl[CH2:20][CH2:19][n:18]1[c:9]([CH2:8][n:7]2[n:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:32]3[c:27]2[cH:28][n:29][cH:30][cH:31]3)[n:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]21.[NH:21]1[CH2:22][CH2:23][CH:24]([OH:25])[CH2:26]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][n:7]([CH2:8][c:9]2[n:10][c:11]3[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3[n:18]2[CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([OH:25])[CH2:26]2)[c:27]2[cH:28][n:29][cH:30][cH:31][c:32]12 | 0.577316 | CC#N.CS(=O)(=O)c1nn(Cc2nc3cc(Cl)ccc3n2CCCl)c2cnccc12.OC1CCNC1>>CS(=O)(=O)c1nn(Cc2nc3cc(Cl)ccc3n2CCN2CCC(O)C2)c2cnccc12 | CC#N.CS(=O)(=O)c1nn(Cc2nc3cc(Cl)ccc3n2CCCl)c2cnccc12.OC1CCNC1>>CS(=O)(=O)c1nn(Cc2nc3cc(Cl)ccc3n2CCN2CCC(O)C2)c2cnccc12 | US09206191B2_0625grants | 9f68d3b7678e4316c1780c3476c443567aca582befeec4c84614f5ef | CC#N.Cl[CH2:20][CH2:19][n:18]1[c:9]([CH2:8][n:7]2[n:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:32]3[c:27]2[cH:28][n:29][cH:30][cH:31]3)[n:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]21.[NH:21]1[CH2:22][CH2:23][CH:24]([OH:25])[CH2:26]1 | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][n:7]([CH2:8][c:9]2[n:10][c:11]3[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3[n:18]2[CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([OH:25])[CH2:26]2)[c:27]2[cH:28][n:29][cH:30][cH:31][c:32]12 | ([C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[C:3])-[C:5])>>(Cl-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | c38df6bb72f417e54d2346e687e032ed86554f208af48effa9422912 | 0.333333 | 3 | CC#N | 138 |
259,001 | 856,495 | 1,425,189 | [CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:24])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][C:16]=2[F:23])=[N:9][N:10]([CH3:14])[C:11]=1[C:12]#[N:13].S(C)C>C(Cl)Cl.B(F)(F)F>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:24])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[F:23])=[N:9][N:10]([CH3:14])[C:11]=1[C:12]#[N:13] | null | US08653112B2_0247 | 2,014 | CSC.C[O:14][c:13]1[cH:12][cH:11][c:10](-[c:9]2[c:8](-[c:7]3[c:2]([CH3:1])[cH:3][s:4][c:5]3[CH3:6])[c:21]([C:22]#[N:23])[n:19]([CH3:20])[n:18]2)[c:16]([F:17])[cH:15]1.ClCCl.FB(F)F>>[CH3:1][c:2]1[cH:3][s:4][c:5]([CH3:6])[c:7]1-[c:8]1[c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[F:17])[n:18][n:19]([CH3:20])[c:21]1[C:22]#[N:23] | 0.975182 | COc1ccc(-c2nn(C)c(C#N)c2-c2c(C)csc2C)c(F)c1.CSC.ClCCl.FB(F)F>>Cc1csc(C)c1-c1c(-c2ccc(O)cc2F)nn(C)c1C#N | COc1ccc(-c2nn(C)c(C#N)c2-c2c(C)csc2C)c(F)c1.CSC.ClCCl.FB(F)F>>Cc1csc(C)c1-c1c(-c2ccc(O)cc2F)nn(C)c1C#N | US08653112B2_0247grants | 0b402b1be10c9aafb9e8f4256534b33595bdaf378da199723e4d9735 | CSC.C[O:14][c:13]1[cH:12][cH:11][c:10](-[c:9]2[c:8](-[c:7]3[c:2]([CH3:1])[cH:3][s:4][c:5]3[CH3:6])[c:21]([C:22]#[N:23])[n:19]([CH3:20])[n:18]2)[c:16]([F:17])[cH:15]1.ClCCl.FB(F)F | [CH3:1][c:2]1[cH:3][s:4][c:5]([CH3:6])[c:7]1-[c:8]1[c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[F:17])[n:18][n:19]([CH3:20])[c:21]1[C:22]#[N:23] | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | CSC.ClCCl.FB(F)F | 48 |
252,963 | 838,692 | 1,392,752 | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[CH:17]=[CH:16][C:12]=2[C:13](O)=[O:14])[CH3:9])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:34]1(OC(N(C)C)=[N+](C)C)[C:38]2C=CC=CC=2N=N1.C(N(CC)CC)C.CN.O1CCCC1>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[CH:17]=[CH:16][C:12]=2[C:13]([NH:34][CH3:38])=[O:14])[CH3:9])=[CH:4][CH:3]=1 | |f:1.2,4.5| | US08586591B2_0995 | 2,013 | C1CCOC1.C1CCOC1.CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F.O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][n:12][cH:13][cH:14][n:15]2)[n:16][c:17]1[NH:18][C@@H:19]([CH3:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][n:12][cH:13][cH:14][n:15]2)[n:16][c:17]1[NH:18][C@@H:19]([CH3:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1 | 0.920789 | C1CCOC1.C1CCOC1~CN.CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.C[C@H](Nc1nc(Nc2cnccn2)ccc1C(=O)O)c1ccc(F)cc1>>CNC(=O)c1ccc(Nc2cnccn2)nc1N[C@@H](C)c1ccc(F)cc1 | C1CCOC1.C1CCOC1.CCN(CC)CC.CN.CN(C)C(On1nnc2ccccc21)=[N+](C)C.C[C@H](Nc1nc(Nc2cnccn2)ccc1C(=O)O)c1ccc(F)cc1.F[P-](F)(F)(F)(F)F>>CNC(=O)c1ccc(Nc2cnccn2)nc1N[C@@H](C)c1ccc(F)cc1 | US08586591B2_0995grants | ae5dcbbd680df40e3946bf6ef4f6d0fbb9e1309230e0a092f9d1d13b | C1CCOC1.C1CCOC1.CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F.O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][n:12][cH:13][cH:14][n:15]2)[n:16][c:17]1[NH:18][C@@H:19]([CH3:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.[CH3:1][NH2:2] | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][n:12][cH:13][cH:14][n:15]2)[n:16][c:17]1[NH:18][C@@H:19]([CH3:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1 | ([#7;a:5]:[c:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C;D1;H3:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[c:4]:[#7;a:5]).([C;D1;H3:6]-[NH2;D1;+0:7]) | c8d3e8be644ca37fe3075935d6d9f9515443e1dc5a5fca512a1988ac | 1 | 1 | C1CCOC1.C1CCOC1.CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | 674 |
187,185 | 646,701 | 1,070,079 | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:29])[C:9]([C:11]1[S:28][C:14]2[C:15]3[CH:23]=[CH:22][C:21]([C:24](OC)=[O:25])=[CH:20][C:16]=3[O:17][CH2:18][CH2:19][C:13]=2[CH:12]=1)=[O:10].[NH2:30][C:31]1([CH2:36][OH:37])[CH2:35][CH2:34][CH2:33][CH2:32]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:29])[C:9]([C:11]1[S:28][C:14]2[C:15]3[CH:23]=[CH:22][C:21]([C:24]([NH:30][C:31]4([CH2:36][OH:37])[CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:25])=[CH:20][C:16]=3[O:17][CH2:18][CH2:19][C:13]=2[CH:12]=1)=[O:10] | null | US07928248B2_0430 | 2,011 | CO[C:14]([c:13]1[cH:12][cH:11][c:10]2[c:25]([cH:24]1)[O:26][CH2:27][CH2:28][c:7]1[cH:6][c:5]([C:3]([N:2]([CH3:1])[c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]3[Cl:35])=[O:4])[s:9][c:8]1-2)=[O:15].[NH2:16][C:17]1([CH2:18][OH:19])[CH2:20][CH2:21][CH2:22][CH2:23]1>>[CH3:1][N:2]([C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([s:9]1)-[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[NH:16][C:17]3([CH2:18][OH:19])[CH2:20][CH2:21][CH2:22][CH2:23]3)[cH:24][c:25]1[O:26][CH2:27][CH2:28]2)[c:29]1[cH:30][cH:31][cH:32][cH:33][c:34]1[Cl:35] | 0.928201 | COC(=O)c1ccc2c(c1)OCCc1cc(C(=O)N(C)c3ccccc3Cl)sc1-2.NC1(CO)CCCC1>>CN(C(=O)c1cc2c(s1)-c1ccc(C(=O)NC3(CO)CCCC3)cc1OCC2)c1ccccc1Cl | COC(=O)c1ccc2c(c1)OCCc1cc(C(=O)N(C)c3ccccc3Cl)sc1-2.NC1(CO)CCCC1>>CN(C(=O)c1cc2c(s1)-c1ccc(C(=O)NC3(CO)CCCC3)cc1OCC2)c1ccccc1Cl | US07928248B2_0430grants | 7fe04723333eef160a70a842591ccae8621a3eaec9dd33af42edc636 | CO[C:14]([c:13]1[cH:12][cH:11][c:10]2[c:25]([cH:24]1)[O:26][CH2:27][CH2:28][c:7]1[cH:6][c:5]([C:3]([N:2]([CH3:1])[c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]3[Cl:35])=[O:4])[s:9][c:8]1-2)=[O:15].[NH2:16][C:17]1([CH2:18][OH:19])[CH2:20][CH2:21][CH2:22][CH2:23]1 | [CH3:1][N:2]([C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([s:9]1)-[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[NH:16][C:17]3([CH2:18][OH:19])[CH2:20][CH2:21][CH2:22][CH2:23]3)[cH:24][c:25]1[O:26][CH2:27][CH2:28]2)[c:29]1[cH:30][cH:31][cH:32][cH:33][c:34]1[Cl:35] | ([C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1)>>(C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1).([C:9]-[NH2;D1;+0:10]) | 63aaae2c5db4d72263ae8d65546a53041de19c5c119633ee758caf10 | 1 | 1 | null | 338 |
38,847 | 174,327 | 279,885 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][NH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:25][CH2:26][C:27](Cl)=[O:28]>ClCCl>[Cl:25][CH2:26][C:27]([N:12]1[C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[S:9][C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:13]1)=[O:28] | null | US05246929_ | 1,993 | CCN(CC)CC.ClCCl.Cl[C:2](=[O:1])[CH2:3][Cl:4].[NH:5]1[CH2:6][C@@H:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[O:1]=[C:2]([CH2:3][Cl:4])[N:5]1[CH2:6][C@@H:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | 0.814128 | CCN(CC)CC.ClCCl.Clc1ccc([C@@H]2CNc3ccccc3S2)cc1.O=C(Cl)CCl>>O=C(CCl)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 | CCN(CC)CC.ClCCl.Clc1ccc([C@@H]2CNc3ccccc3S2)cc1.O=C(Cl)CCl>>O=C(CCl)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 | US05246929_grants | 5b70e9be1129ead81780c28daa29aa420ed246be9741199c1a0591ea | CCN(CC)CC.ClCCl.Cl[C:2](=[O:1])[CH2:3][Cl:4].[NH:5]1[CH2:6][C@@H:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | [O:1]=[C:2]([CH2:3][Cl:4])[N:5]1[CH2:6][C@@H:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[c:6])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[c:6]) | 243d4d70ed956e3ba4e5bc0d489e1112d3a0eba27892f1d71f3a13af | 1 | 1 | CCN(CC)CC.ClCCl | 160 |
278,847 | 913,578 | 1,527,469 | [CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][C@H:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[CH2:10]2)[N:3]=1.[F:20][C:21]1[CH:22]=[C:23]([S:28](Cl)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1[F:27]>ClCCl.N1C=CC=CC=1>[F:20][C:21]1[CH:22]=[C:23]([S:28]([NH:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([N:9]3[CH2:13][CH2:12][C@H:11]([N:14]4[CH2:18][CH2:17][CH2:16][C@@H:15]4[CH3:19])[CH2:10]3)=[CH:5][CH:6]=2)(=[O:29])=[O:30])[CH:24]=[CH:25][C:26]=1[F:27] | null | US08859588B2_0217 | 2,014 | ClCCl.Cl[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:29])[cH:30]1.[CH3:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][C@H:8]([N:9]3[CH2:10][CH2:11][CH2:12][C@@H:13]3[CH3:14])[CH2:15]2)[cH:16][cH:17][c:18]1[NH2:19].c1ccncc1>>[CH3:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][C@H:8]([N:9]3[CH2:10][CH2:11][CH2:12][C@@H:13]3[CH3:14])[CH2:15]2)[cH:16][cH:17][c:18]1[NH:19][S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:29])[cH:30]1 | 0.740102 | Cc1nc(N2CC[C@H](N3CCC[C@@H]3C)C2)ccc1N.ClCCl.O=S(=O)(Cl)c1ccc(F)c(F)c1.c1ccncc1>>Cc1nc(N2CC[C@H](N3CCC[C@@H]3C)C2)ccc1NS(=O)(=O)c1ccc(F)c(F)c1 | Cc1nc(N2CC[C@H](N3CCC[C@@H]3C)C2)ccc1N.ClCCl.O=S(=O)(Cl)c1ccc(F)c(F)c1.c1ccncc1>>Cc1nc(N2CC[C@H](N3CCC[C@@H]3C)C2)ccc1NS(=O)(=O)c1ccc(F)c(F)c1 | US08859588B2_0217grants | 445450384aced8fa444fe89468b7456cb2b7000ce53bf49091c350fa | ClCCl.Cl[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:29])[cH:30]1.[CH3:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][C@H:8]([N:9]3[CH2:10][CH2:11][CH2:12][C@@H:13]3[CH3:14])[CH2:15]2)[cH:16][cH:17][c:18]1[NH2:19].c1ccncc1 | [CH3:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][C@H:8]([N:9]3[CH2:10][CH2:11][CH2:12][C@@H:13]3[CH3:14])[CH2:15]2)[cH:16][cH:17][c:18]1[NH:19][S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:29])[cH:30]1 | ([#7;a:5]:[c:6]:[c:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([#7;a:5]:[c:6]:[c:7]-[NH2;D1;+0:8]) | a9f619a0cc7a836039dce0485f1c15d38971ace6133f992047085082 | 1 | 1 | ClCCl.c1ccncc1 | 554 |