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
|
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
422,129 | 1,775,497 | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[C:19]([CH3:22])=[N:20][N:21]=[C:11]3[CH:10]([CH2:23][C:24]([OH:26])=O)[CH:9]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[O:59]([CH:66]1[CH2:69][NH:68][CH2:67]1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[C:19]([CH3:22])=[N:20][N:21]=[C:11]3[CH:10]([CH2:23][C:24]([N:68]3[CH2:67][CH:66]([O:59][C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)[CH2:69]3)=[O:26])[CH:9]=2)=[CH:6][CH:7]=1 | |f:1.2,4.5| | US20150299201A1_0654 | 2,015 | CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:24]([CH2:23][CH:22]1[c:5]2[n:4][n:3][c:2]([CH3:1])[n:6]2-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]([c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)=[CH:21]1)=[O:25].[NH:26]1[CH2:27][CH:28]([O:29][c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[CH2:36]1>>[CH3:1][c:2]1[n:3][n:4][c:5]2[n:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]([c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1)=[CH:21][CH:22]2[CH2:23][C:24](=[O:25])[N:26]1[CH2:27][CH:28]([O:29][c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[CH2:36]1 | 0.655721 | CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.Cc1nnc2n1-c1ccccc1C(c1ccc(Cl)cc1)=CC2CC(=O)O.Cl~c1ccc(OC2CNC2)cc1>>Cc1nnc2n1-c1ccccc1C(c1ccc(Cl)cc1)=CC2CC(=O)N1CC(Oc2ccccc2)C1 | CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cc1nnc2n1-c1ccccc1C(c1ccc(Cl)cc1)=CC2CC(=O)O.Cl.F[P-](F)(F)(F)(F)F.c1ccc(OC2CNC2)cc1>>Cc1nnc2n1-c1ccccc1C(c1ccc(Cl)cc1)=CC2CC(=O)N1CC(Oc2ccccc2)C1 | US20150299201A1_0654apps | 92a4a6fb90e272842d8a633da050162ed79cf5cb3df7070e397a3490 | CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:24]([CH2:23][CH:22]1[c:5]2[n:4][n:3][c:2]([CH3:1])[n:6]2-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]([c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)=[CH:21]1)=[O:25].[NH:26]1[CH2:27][CH:28]([O:29][c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[CH2:36]1 | [CH3:1][c:2]1[n:3][n:4][c:5]2[n:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]([c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1)=[CH:21][CH:22]2[CH2:23][C:24](=[O:25])[N:26]1[CH2:27][CH:28]([O:29][c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[CH2:36]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 | CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F | 146 |
151,235 | 540,320 | 904,731 | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][OH:16])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][O:16][S:24]([CH3:23])(=[O:26])=[O:25])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2] | null | US07547691B2_0105 | 2,009 | ClCCl.Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C:2]1([CH2:3][OH:4])[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.c1ccncc1>>[CH3:1][C:2]1([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1 | 0.217955 | CC1(CO)CCN(C(=O)OC(C)(C)C)CC1.CS(=O)(=O)Cl.ClCCl.c1ccncc1>>CC1(COS(C)(=O)=O)CCN(C(=O)OC(C)(C)C)CC1 | CC1(CO)CCN(C(=O)OC(C)(C)C)CC1.CS(=O)(=O)Cl.ClCCl.c1ccncc1>>CC1(COS(C)(=O)=O)CCN(C(=O)OC(C)(C)C)CC1 | US07547691B2_0105grants | 4dc1aa9d0b84959892744dbbbe0f085afdc571a054771125fae3687c | ClCCl.Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C:2]1([CH2:3][OH:4])[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.c1ccncc1 | [CH3:1][C:2]1([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | ClCCl.c1ccncc1 | 0 |
3,511 | 18,429 | 24,014 | O.Cl.C1(C)C=CC=CC=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=O)[CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:19][CH:18]=2)=[CH:13][C:12]=1[Br:30]>[Zn].O1CCOCC1>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:21][CH:22]=2)=[CH:13][C:12]=1[Br:30] | null | US04021479_ | 1,977 | C1COCCO1.Cc1ccccc1.Cl.O.O=[C:10]([c:9]1[cH:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([NH2:1])[c:19]([Br:20])[cH:18]2)[cH:17][cH:16]1)[CH2:11][CH2:12][C:13](=[O:14])[OH:15].[Zn]>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([CH2:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH:17]2)[cH:18][c:19]1[Br:20] | 0.927233 | C1COCCO1.Cc1ccccc1.Cl.Nc1ccc(-c2ccc(C(=O)CCC(=O)O)cc2)cc1Br.O.[Zn]>>Nc1ccc(-c2ccc(CCCC(=O)O)cc2)cc1Br | C1COCCO1.Cc1ccccc1.Cl.Nc1ccc(-c2ccc(C(=O)CCC(=O)O)cc2)cc1Br.O.[Zn]>>Nc1ccc(-c2ccc(CCCC(=O)O)cc2)cc1Br | US04021479_grants | b5d17943f63d731a16ca5c3cb0e2dc73b37a28d792f32f8cf656eb86 | C1COCCO1.Cc1ccccc1.Cl.O.O=[C:10]([c:9]1[cH:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([NH2:1])[c:19]([Br:20])[cH:18]2)[cH:17][cH:16]1)[CH2:11][CH2:12][C:13](=[O:14])[OH:15].[Zn] | [NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([CH2:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH:17]2)[cH:18][c:19]1[Br:20] | ([C:2]-[CH2;D2;+0:1]-[c:3])>>(O=[C;H0;D3;+0:1](-[C:2])-[c:3]) | 874f533cb23b97c467028e6036fbaafdbd21166dcb2c66b52ef718e1 | 1 | 1 | C1COCCO1.Cc1ccccc1.Cl.O.[Zn] | 92 |
428,119 | 1,823,133 | null | [Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]([CH3:13])[CH2:10][C:11]#[N:12])[C:5]([N+:14]([O-])=O)=[CH:4][N:3]=1.[Cl-].[NH4+].O>C(O)C.[Fe]>[NH2:14][C:5]1[C:6]([NH:8][CH:9]([CH3:13])[CH2:10][C:11]#[N:12])=[CH:7][C:2]([Br:1])=[N:3][CH:4]=1 | |f:1.2| | US20160016948A1_1468 | 2,016 | CCO.O.O=[N+:14]([O-])[c:13]1[c:7]([NH:6][CH:2]([CH3:1])[CH2:3][C:4]#[N:5])[cH:8][c:9]([Br:10])[n:11][cH:12]1.[Cl-].[Fe].[NH4+]>>[CH3:1][CH:2]([CH2:3][C:4]#[N:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[n:11][cH:12][c:13]1[NH2:14] | 0.996115 | CC(CC#N)Nc1cc(Br)ncc1[N+](=O)[O-].CCO.O.[Cl-]~[NH4+].[Fe]>>CC(CC#N)Nc1cc(Br)ncc1N | CC(CC#N)Nc1cc(Br)ncc1[N+](=O)[O-].CCO.O.[Cl-].[Fe].[NH4+]>>CC(CC#N)Nc1cc(Br)ncc1N | US20160016948A1_1468apps | 843f517076990eaa5ccf3cd3c8a610e22999c0f5af4e20b226f47d82 | CCO.O.O=[N+:14]([O-])[c:13]1[c:7]([NH:6][CH:2]([CH3:1])[CH2:3][C:4]#[N:5])[cH:8][c:9]([Br:10])[n:11][cH:12]1.[Cl-].[Fe].[NH4+] | [CH3:1][CH:2]([CH2:3][C:4]#[N:5])[NH:6][c:7]1[cH:8][c:9]([Br:10])[n:11][cH:12][c:13]1[NH2:14] | ([#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 | CCO.O.[Cl-].[Fe].[NH4+] | 269 |
283,769 | 928,431 | 1,554,278 | F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:17]=2)[N:10]=1.[F:27][C:28]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:29]=1[CH2:30][OH:31]>>[F:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:17]=3)[N:10]=2)=[C:2]([O:31][CH2:30][C:29]2[CH:32]=[C:33]([F:37])[C:34]([F:36])=[CH:35][C:28]=2[F:27])[CH:7]=1 | null | US08916557B2_1035 | 2,014 | F[c:23]1[c:17](-[c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[cH:9][cH:8][cH:7][c:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:36]3)[n:35]2)[cH:18][cH:19][c:20]([F:21])[cH:22]1.[OH:24][CH2:25][c:26]1[cH:27][c:28]([F:29])[c:30]([F:31])[cH:32][c:33]1[F:34]>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][n:15][c:16](-[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][c:23]3[O:24][CH2:25][c:26]3[cH:27][c:28]([F:29])[c:30]([F:31])[cH:32][c:33]3[F:34])[n:35]2)[cH:36]1 | 0.53665 | CS(=O)(=O)Cc1cccc(Nc2ncnc(-c3ccc(F)cc3F)n2)c1.OCc1cc(F)c(F)cc1F>>CS(=O)(=O)Cc1cccc(Nc2ncnc(-c3ccc(F)cc3OCc3cc(F)c(F)cc3F)n2)c1 | CS(=O)(=O)Cc1cccc(Nc2ncnc(-c3ccc(F)cc3F)n2)c1.OCc1cc(F)c(F)cc1F>>CS(=O)(=O)Cc1cccc(Nc2ncnc(-c3ccc(F)cc3OCc3cc(F)c(F)cc3F)n2)c1 | US08916557B2_1035grants | b8907d867d3cb8e3419a41e78669c44564e80a89c0c663155ede8e2d | F[c:23]1[c:17](-[c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[cH:9][cH:8][cH:7][c:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:36]3)[n:35]2)[cH:18][cH:19][c:20]([F:21])[cH:22]1.[OH:24][CH2:25][c:26]1[cH:27][c:28]([F:29])[c:30]([F:31])[cH:32][c:33]1[F:34] | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][n:15][c:16](-[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][c:23]3[O:24][CH2:25][c:26]3[cH:27][c:28]([F:29])[c:30]([F:31])[cH:32][c:33]3[F:34])[n:35]2)[cH:36]1 | ([C:4]-[O;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[OH;D1;+0:5]) | 5e910f78c09147f95443e74bed5b26e7557d68f73dba61bcb03d2b4e | 1 | 1 | null | 485 |
92,530 | 362,868 | 618,719 | [OH:1][C@H:2]1[C@@H:6]([OH:7])[CH2:5][O:4][CH2:3]1.Br[CH2:9][CH:10]1[CH2:12][CH2:11]1.[H-].[Na+]>CN(C=O)C>[CH:10]1([CH2:9][O:1][C@H:2]2[C@@H:6]([OH:7])[CH2:5][O:4][CH2:3]2)[CH2:12][CH2:11]1 | |f:2.3| | US06610692B1_ | 2,003 | Br[CH2:8][CH:9]1[CH2:10][CH2:11]1.CN(C)C=O.[H-].[Na+].[OH:1][C@H:2]1[CH2:3][O:4][CH2:5][C@H:6]1[OH:7]>>[OH:1][C@H:2]1[CH2:3][O:4][CH2:5][C@H:6]1[O:7][CH2:8][CH:9]1[CH2:10][CH2:11]1 | 0.788071 | BrCC1CC1.CN(C)C=O.O[C@H]1COC[C@H]1O.[H-]~[Na+]>>O[C@H]1COC[C@H]1OCC1CC1 | BrCC1CC1.CN(C)C=O.O[C@H]1COC[C@H]1O.[H-].[Na+]>>O[C@H]1COC[C@H]1OCC1CC1 | US06610692B1_grants | a1e7ae64c00f7bdd0153f55434200e40f29d037722f3d74c642efd63 | Br[CH2:8][CH:9]1[CH2:10][CH2:11]1.CN(C)C=O.[H-].[Na+].[OH:1][C@H:2]1[CH2:3][O:4][CH2:5][C@H:6]1[OH:7] | [OH:1][C@H:2]1[CH2:3][O:4][CH2:5][C@H:6]1[O:7][CH2:8][CH:9]1[CH2:10][CH2:11]1 | ([C:3]-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2])>>(Br-[CH2;D2;+0:1]-[C:2]).([C:3]-[OH;D1;+0:4]) | a4c3d230363503c3cdd0e8b3bb15c888472ef0fddbf2cfc06e03712b | 0.333333 | 3 | CN(C)C=O.[H-].[Na+] | 95 |
113,288 | 425,668 | 725,907 | Cl.[NH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:13].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[C:23](O)=[O:24]>>[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[C:23]([NH:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:13])=[O:24] | |f:0.1| | US07057046B2_0399 | 2,006 | Cl.O[C:2](=[O:1])[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[nH:23]1.[NH2:3][CH:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14])[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[nH:23]1 | 0.86863 | Cl~NC1Cc2ccccc2NC1=O.O=C(O)c1cc2ccccc2[nH]1>>O=C(NC1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | Cl.NC1Cc2ccccc2NC1=O.O=C(O)c1cc2ccccc2[nH]1>>O=C(NC1Cc2ccccc2NC1=O)c1cc2ccccc2[nH]1 | US07057046B2_0399grants | 3cba5e3af3176aefd8d272d228826bc144c831222d8e5e71c1eeb80b | Cl.O[C:2](=[O:1])[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[nH:23]1.[NH2:3][CH:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14] | [O:1]=[C:2]([NH:3][CH:4]1[CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]1=[O:14])[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[nH:23]1 | ([#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4]).([#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH2;D1;+0:9]) | 546a55c3d78e1abfb45a6fd70c1258135f9210dbe24a516c25687c81 | 1 | 1 | Cl | 738 |
97,499 | 377,498 | 646,295 | I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[C:11](=[O:14])([O-])[O-].[K+].[K+]>N1CCCC1=O.O.[Cu]>[N+:8]([C:4]1[CH:3]=[C:2]([N:8]2[CH2:4][CH2:3][CH2:2][C:11]2=[O:14])[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9] | |f:1.2.3| | US06723735B1_ | 2,004 | I[c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1.O.O=C([O-])[O-].[Cu].[K+].[K+].[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][NH:6]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | 0.960621 | O.O=C([O-])[O-]~[K+]~[K+].O=C1CCCN1.O=[N+]([O-])c1cccc(I)c1.[Cu]>>O=C1CCCN1c1cccc([N+](=O)[O-])c1 | O.O=C([O-])[O-].O=C1CCCN1.O=[N+]([O-])c1cccc(I)c1.[Cu].[K+].[K+]>>O=C1CCCN1c1cccc([N+](=O)[O-])c1 | US06723735B1_grants | b403361c6134d979b85b9f140d5e0695e55ee403ea391ba6b4a10980 | I[c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1.O.O=C([O-])[O-].[Cu].[K+].[K+].[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][NH:6]1 | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | ([C:4]-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7](-[C:8])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(I-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]) | ab9b05ecea2fd8d462198cc8d25e942aaadbafd65ede50c12e758706 | 1 | 1 | O.O=C([O-])[O-].[Cu].[K+].[K+] | 921 |
185,422 | 641,734 | 1,061,480 | [CH2:1]([N:3]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[CH:25]=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C>[CH2:1]([N:3]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:17][C:16]=1[CH2:25][OH:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2] | |f:1.2,3.4| | US07906517B2_0511 | 2,011 | CCO.CCOC(C)=O.Cc1ccccc1.[BH4-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[c:15]1[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24]1[CH:25]=[O:26].[Cl-].[NH4+].[Na+]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[c:15]1[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24]1[CH2:25][OH:26] | 0.259976 | CCO.CCOC(=O)CCCCCCN(CC)c1ccc(C(F)(F)F)cc1C=O.CCOC(C)=O.Cc1ccccc1.[BH4-]~[Na+].[Cl-]~[NH4+]>>CCOC(=O)CCCCCCN(CC)c1ccc(C(F)(F)F)cc1CO | CCO.CCOC(=O)CCCCCCN(CC)c1ccc(C(F)(F)F)cc1C=O.CCOC(C)=O.Cc1ccccc1.[BH4-].[Cl-].[NH4+].[Na+]>>CCOC(=O)CCCCCCN(CC)c1ccc(C(F)(F)F)cc1CO | US07906517B2_0511grants | cd823d19427e8a01295e0b3d433708371b500fe0aa0b102c3dc8c28d | CCO.CCOC(C)=O.Cc1ccccc1.[BH4-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[c:15]1[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24]1[CH:25]=[O:26].[Cl-].[NH4+].[Na+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[c:15]1[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24]1[CH2:25][OH:26] | ([OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3])>>([O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]) | 840c26c06ae3d1e03b5c3844632a3543b6d18e6db9d7ee28fbdda31c | 1 | 1 | CCO.CCOC(C)=O.Cc1ccccc1.[BH4-].[Cl-].[NH4+].[Na+] | 356 |
191,485 | 659,659 | 1,091,933 | C(N(CC)CC)C.[CH2:8]([N:11]=[C:12]=[O:13])[CH2:9][CH3:10].[NH2:14][C:15]([NH:17][C:18]1[NH:19][C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[OH:32])=[CH:21][C:22]=1[C:23]([NH2:25])=[O:24])=[O:16]>CN(C)C=O>[NH2:14][C:15]([NH:17][C:18]1[NH:19][C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][C:12]([NH:11][CH2:8][CH2:9][CH3:10])=[O:13])=[CH:21][C:22]=1[C:23]([NH2:25])=[O:24])=[O:16] | null | US07977371B2_0378 | 2,011 | CCN(CC)CC.CN(C)C=O.[CH3:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[OH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1-[c:14]1[cH:15][c:16]([C:17]([NH2:18])=[O:19])[c:20]([NH:21][C:22]([NH2:23])=[O:24])[nH:25]1>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1-[c:14]1[cH:15][c:16]([C:17]([NH2:18])=[O:19])[c:20]([NH:21][C:22]([NH2:23])=[O:24])[nH:25]1 | 0.970843 | CCCN=C=O.CCN(CC)CC.CN(C)C=O.NC(=O)Nc1[nH]c(-c2ccccc2O)cc1C(N)=O>>CCCNC(=O)Oc1ccccc1-c1cc(C(N)=O)c(NC(N)=O)[nH]1 | CCCN=C=O.CCN(CC)CC.CN(C)C=O.NC(=O)Nc1[nH]c(-c2ccccc2O)cc1C(N)=O>>CCCNC(=O)Oc1ccccc1-c1cc(C(N)=O)c(NC(N)=O)[nH]1 | US07977371B2_0378grants | 16b1faadbc96ddae19f6fd838f2c8673562a7b873856135f45e5f5b7 | CCN(CC)CC.CN(C)C=O.[CH3:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[OH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1-[c:14]1[cH:15][c:16]([C:17]([NH2:18])=[O:19])[c:20]([NH:21][C:22]([NH2:23])=[O:24])[nH:25]1 | [CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1-[c:14]1[cH:15][c:16]([C:17]([NH2:18])=[O:19])[c:20]([NH:21][C:22]([NH2:23])=[O:24])[nH:25]1 | ([C:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[c:6])>>([C:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4]).([OH;D1;+0:5]-[c:6]) | 117aac3b9c4fbb4e956ceb6389df5b638b95774fadf9bbcae7874889 | 1 | 1 | CCN(CC)CC.CN(C)C=O | 104 |
138,305 | 500,179 | 841,002 | [NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[C:13](O[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O>C(Cl)Cl>[C:16]([O:15][C:13]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17] | null | US07384952B2_0536 | 2,008 | CC(C)(C)OC(=O)O[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].ClCCl.O.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH2:10])[cH:18][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19]1 | 0.289083 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.COC(=O)c1ccc(CN)cc1.ClCCl.O>>COC(=O)c1ccc(CNC(=O)OC(C)(C)C)cc1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.COC(=O)c1ccc(CN)cc1.ClCCl.O>>COC(=O)c1ccc(CNC(=O)OC(C)(C)C)cc1 | US07384952B2_0536grants | 0d8cf4e2685ae8763ee75686586c413772a0b0c8bcb1e957cfd28d3f | CC(C)(C)OC(=O)O[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].ClCCl.O.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH2:10])[cH:18][cH:19]1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19]1 | ([C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[c:14]:[c:15]:1)>>(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]).([NH2;D1;+0:8]-[C:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[c:14]:[c:15]:1) | 99fbb0070a9da6d11e987da55ba5465058f85284f4cc3723d6e3da97 | 1 | 1 | ClCCl.O | 686 |
413,885 | 1,692,493 | null | S(=O)(=O)(O)O.[Cl:6][C:7]1[C:8]([CH:37]2OCC[O:38]2)=[C:9]([O:32][C:33]([F:36])([F:35])[F:34])[CH:10]=[C:11]2[C:16]=1[NH:15][C:14](=[O:17])[N:13]([CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])[C:12]2=[O:31]>CN1C(=O)CCC1.O>[Cl:6][C:7]1[C:8]([CH:37]=[O:38])=[C:9]([O:32][C:33]([F:34])([F:36])[F:35])[CH:10]=[C:11]2[C:16]=1[NH:15][C:14](=[O:17])[N:13]([CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[S:26]([CH2:29][CH3:30])(=[O:27])=[O:28])[C:12]2=[O:31] | null | US20150141400A1_0411 | 2,015 | C1C[O:23][CH:22]([c:21]2[c:19]([Cl:20])[c:18]3[nH:17][c:15](=[O:16])[n:14]([CH2:13][c:12]4[c:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:7][cH:8][c:9]([Cl:10])[cH:11]4)[c:32](=[O:33])[c:31]3[cH:30][c:24]2[O:25][C:26]([F:27])([F:28])[F:29])O1.CN1CCCC1=O.O.O=S(=O)(O)O>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[CH2:13][n:14]1[c:15](=[O:16])[nH:17][c:18]2[c:19]([Cl:20])[c:21]([CH:22]=[O:23])[c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30][c:31]2[c:32]1=[O:33] | 0.092028 | CCS(=O)(=O)c1ccc(Cl)cc1Cn1c(=O)[nH]c2c(Cl)c(C3OCCO3)c(OC(F)(F)F)cc2c1=O.CN1CCCC1=O.O.O=S(=O)(O)O>>CCS(=O)(=O)c1ccc(Cl)cc1Cn1c(=O)[nH]c2c(Cl)c(C=O)c(OC(F)(F)F)cc2c1=O | CCS(=O)(=O)c1ccc(Cl)cc1Cn1c(=O)[nH]c2c(Cl)c(C3OCCO3)c(OC(F)(F)F)cc2c1=O.CN1CCCC1=O.O.O=S(=O)(O)O>>CCS(=O)(=O)c1ccc(Cl)cc1Cn1c(=O)[nH]c2c(Cl)c(C=O)c(OC(F)(F)F)cc2c1=O | US20150141400A1_0411apps | 256c6c613f0bcc4b60b6dc14e854cea5f9162d89ad8236a058def692 | C1C[O:23][CH:22]([c:21]2[c:19]([Cl:20])[c:18]3[nH:17][c:15](=[O:16])[n:14]([CH2:13][c:12]4[c:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:7][cH:8][c:9]([Cl:10])[cH:11]4)[c:32](=[O:33])[c:31]3[cH:30][c:24]2[O:25][C:26]([F:27])([F:28])[F:29])O1.CN1CCCC1=O.O.O=S(=O)(O)O | [CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[CH2:13][n:14]1[c:15](=[O:16])[nH:17][c:18]2[c:19]([Cl:20])[c:21]([CH:22]=[O:23])[c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30][c:31]2[c:32]1=[O:33] | ([O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1)>>(C1-C-[O;H0;D2;+0:1]-[CH;D3;+0:2](-[c:3]2:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:2)-O-1) | 260a276baaaafdec880b5432fe6997842a3d47310c01fb3061496f27 | 1 | 1 | CN1CCCC1=O.O.O=S(=O)(O)O | 655 |
92,537 | 362,887 | 618,931 | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.[CH:28]1([CH2:33][CH:34]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=2)[C:35]([OH:37])=O)[CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:46][C:47]1[CH:54]=[CH:53][C:50]([C:51]#[N:52])=[CH:49][N:48]=1.N1C=CC=CC=1>C(Cl)Cl.O>[C:51]([C:50]1[CH:53]=[CH:54][C:47]([NH:46][C:35](=[O:37])[CH:34]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=2)[CH2:33][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)=[N:48][CH:49]=1)#[N:52] | null | US06610846B1_ | 2,003 | ClCCl.O.O=C1CCC(=O)N1Br.O[C:8](=[O:9])[CH:10]([CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:25][cH:26]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccncc1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]2[cH:18][cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]2)[n:25][cH:26]1 | 0.822953 | ClCCl.N#Cc1ccc(N)nc1.O.O=C(O)C(CC1CCCC1)c1ccc(Cl)c(Cl)c1.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccncc1>>N#Cc1ccc(NC(=O)C(CC2CCCC2)c2ccc(Cl)c(Cl)c2)nc1 | ClCCl.N#Cc1ccc(N)nc1.O.O=C(O)C(CC1CCCC1)c1ccc(Cl)c(Cl)c1.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccncc1>>N#Cc1ccc(NC(=O)C(CC2CCCC2)c2ccc(Cl)c(Cl)c2)nc1 | US06610846B1_grants | b324bf85e8815a4cdffdfadb88b98e588ba5d9e4eb6cb09e8cf4c003 | ClCCl.O.O=C1CCC(=O)N1Br.O[C:8](=[O:9])[CH:10]([CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:25][cH:26]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccncc1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]2[cH:18][cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]2)[n:25][cH:26]1 | ([#7;a:4]:[c:5]-[NH;D2;+0:6]-[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]:[c:5]-[NH2;D1;+0:6]) | 66a1af7030b76915ceb0ef4051d4ecefc5703f73df43b291fa25ac95 | 1 | 1 | ClCCl.O.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccncc1 | 368 |
26,328 | 123,203 | 199,141 | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[CH3:20][N:21]([CH3:26])[S:22](Cl)(=[O:24])=[O:23].Cl>N1C=CC=CC=1>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[O:11][C:3]1[CH:4]=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[NH:1][S:22](=[O:24])(=[O:23])[N:21]([CH3:26])[CH3:20] | null | US04866091_ | 1,989 | Cl.Cl[S:9](=[O:10])(=[O:11])[N:12]([CH3:13])[CH3:14].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:15]([O:16][c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][c:23]2[F:24])[cH:25]1.c1ccncc1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[N:12]([CH3:13])[CH3:14])[c:15]([O:16][c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][c:23]2[F:24])[cH:25]1 | 0.36446 | CC(=O)c1ccc(N)c(Oc2ccc(F)cc2F)c1.CN(C)S(=O)(=O)Cl.Cl.c1ccncc1>>CC(=O)c1ccc(NS(=O)(=O)N(C)C)c(Oc2ccc(F)cc2F)c1 | CC(=O)c1ccc(N)c(Oc2ccc(F)cc2F)c1.CN(C)S(=O)(=O)Cl.Cl.c1ccncc1>>CC(=O)c1ccc(NS(=O)(=O)N(C)C)c(Oc2ccc(F)cc2F)c1 | US04866091_grants | e624c4bc2338f9dc02874a11ff4fa604540bc85079a656ec17689abf | Cl.Cl[S:9](=[O:10])(=[O:11])[N:12]([CH3:13])[CH3:14].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:15]([O:16][c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][c:23]2[F:24])[cH:25]1.c1ccncc1 | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[N:12]([CH3:13])[CH3:14])[c:15]([O:16][c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][c:23]2[F:24])[cH:25]1 | ([#7:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6])>>(Cl-[S;H0;D4;+0:1](-[#7:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([NH2;D1;+0:5]-[c:6]) | 788489906bba5b68fc89247772f025cc40715a74429ca9eadd92fec4 | 1 | 1 | Cl.c1ccncc1 | 395 |
152,204 | 543,481 | 909,808 | [C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)([OH:3])=O.[F:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)[NH2:28]>>[F:21][C@@H:19]1[CH2:20][N:16]([C:14](=[O:15])[CH2:13][NH:12][C:7]23[CH2:8][CH2:9][C:4]([C:1]([NH:28][C:27]4[CH:29]=[CH:30][C:31]([N:32]5[CH2:33][CH2:34][O:35][CH2:36][CH2:37]5)=[C:25]([F:24])[CH:26]=4)=[O:3])([CH2:11][CH2:10]2)[CH2:5][CH2:6]3)[C@H:17]([C:22]#[N:23])[CH2:18]1 | null | US07560569B2_0589 | 2,009 | O[C:17]([C:16]12[CH2:15][CH2:14][C:13]([NH:12][CH2:11][C:9]([N:8]3[C@H:3]([C:2]#[N:1])[CH2:4][C@H:5]([F:6])[CH2:7]3)=[O:10])([CH2:34][CH2:33]1)[CH2:36][CH2:35]2)=[O:18].[NH2:19][c:20]1[cH:21][cH:22][c:23]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[c:30]([F:31])[cH:32]1>>[N:1]#[C:2][C@@H:3]1[CH2:4][C@H:5]([F:6])[CH2:7][N:8]1[C:9](=[O:10])[CH2:11][NH:12][C:13]12[CH2:14][CH2:15][C:16]([C:17](=[O:18])[NH:19][c:20]3[cH:21][cH:22][c:23]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[c:30]([F:31])[cH:32]3)([CH2:33][CH2:34]1)[CH2:35][CH2:36]2 | 0.640086 | N#C[C@@H]1C[C@H](F)CN1C(=O)CNC12CCC(C(=O)O)(CC1)CC2.Nc1ccc(N2CCOCC2)c(F)c1>>N#C[C@@H]1C[C@H](F)CN1C(=O)CNC12CCC(C(=O)Nc3ccc(N4CCOCC4)c(F)c3)(CC1)CC2 | N#C[C@@H]1C[C@H](F)CN1C(=O)CNC12CCC(C(=O)O)(CC1)CC2.Nc1ccc(N2CCOCC2)c(F)c1>>N#C[C@@H]1C[C@H](F)CN1C(=O)CNC12CCC(C(=O)Nc3ccc(N4CCOCC4)c(F)c3)(CC1)CC2 | US07560569B2_0589grants | 3d18ff0b8e3a69f981e7b1c46a70171fabcce5ecd4c2613e06db9cf6 | O[C:17]([C:16]12[CH2:15][CH2:14][C:13]([NH:12][CH2:11][C:9]([N:8]3[C@H:3]([C:2]#[N:1])[CH2:4][C@H:5]([F:6])[CH2:7]3)=[O:10])([CH2:34][CH2:33]1)[CH2:36][CH2:35]2)=[O:18].[NH2:19][c:20]1[cH:21][cH:22][c:23]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[c:30]([F:31])[cH:32]1 | [N:1]#[C:2][C@@H:3]1[CH2:4][C@H:5]([F:6])[CH2:7][N:8]1[C:9](=[O:10])[CH2:11][NH:12][C:13]12[CH2:14][CH2:15][C:16]([C:17](=[O:18])[NH:19][c:20]3[cH:21][cH:22][c:23]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[c:30]([F:31])[cH:32]3)([CH2:33][CH2:34]1)[CH2:35][CH2:36]2 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | 993a80a34f6acdc22e1630fbdadc440460d93877c75dd17e7db680f0 | 1 | 1 | null | 365 |
196,951 | 674,602 | 1,114,448 | [CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][N:8]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=5[F:38])[CH:33]=O)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[C:50]([N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)(=[O:52])[CH3:51]>>[C:50]([N:53]1[CH2:58][CH2:57][N:56]([CH2:33][C:32]2[CH:35]=[CH:36][C:37]([F:38])=[C:30]([N:27]3[C:17]4[N:18]=[C:19]([N:21]5[CH2:22][CH2:23][O:24][CH2:25][CH2:26]5)[N:20]=[C:15]([C:12]5[CH:11]=[N:10][C:9]([N:8]([CH2:39][C:40]6[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=6)[CH2:7][C:6]6[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:49][CH:48]=6)=[N:14][CH:13]=5)[C:16]=4[CH2:29][CH2:28]3)[CH:31]=2)[CH2:55][CH2:54]1)(=[O:52])[CH3:51] | null | US08022205B2_2589 | 2,011 | O=[CH:40][c:39]1[cH:38][c:37]([N:36]2[c:32]3[n:31][c:24]([N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)[n:23][c:22](-[c:21]4[cH:20][n:19][c:18]([N:8]([CH2:7][c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:57][cH:56]5)[CH2:9][c:10]5[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]5)[n:55][cH:54]4)[c:33]3[CH2:34][CH2:35]2)[c:52]([F:53])[cH:51][cH:50]1.[NH:41]1[CH2:42][CH2:43][N:44]([C:45]([CH3:46])=[O:47])[CH2:48][CH2:49]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[c:18]2[n:19][cH:20][c:21](-[c:22]3[n:23][c:24]([N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)[n:31][c:32]4[c:33]3[CH2:34][CH2:35][N:36]4[c:37]3[cH:38][c:39]([CH2:40][N:41]4[CH2:42][CH2:43][N:44]([C:45]([CH3:46])=[O:47])[CH2:48][CH2:49]4)[cH:50][cH:51][c:52]3[F:53])[cH:54][n:55]2)[cH:56][cH:57]1 | 0.841361 | CC(=O)N1CCNCC1.COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4c3cc(C=O)ccc3F)cn2)cc1>>COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4c3cc(CN4CCN(C(C)=O)CC4)ccc3F)cn2)cc1 | CC(=O)N1CCNCC1.COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4c3cc(C=O)ccc3F)cn2)cc1>>COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4c3cc(CN4CCN(C(C)=O)CC4)ccc3F)cn2)cc1 | US08022205B2_2589grants | 1b52ecd78afcf199ea613f0598f35ddd6879de004359d82fb9de5e10 | O=[CH:40][c:39]1[cH:38][c:37]([N:36]2[c:32]3[n:31][c:24]([N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)[n:23][c:22](-[c:21]4[cH:20][n:19][c:18]([N:8]([CH2:7][c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:57][cH:56]5)[CH2:9][c:10]5[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]5)[n:55][cH:54]4)[c:33]3[CH2:34][CH2:35]2)[c:52]([F:53])[cH:51][cH:50]1.[NH:41]1[CH2:42][CH2:43][N:44]([C:45]([CH3:46])=[O:47])[CH2:48][CH2:49]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[c:18]2[n:19][cH:20][c:21](-[c:22]3[n:23][c:24]([N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)[n:31][c:32]4[c:33]3[CH2:34][CH2:35][N:36]4[c:37]3[cH:38][c:39]([CH2:40][N:41]4[CH2:42][CH2:43][N:44]([C:45]([CH3:46])=[O:47])[CH2:48][CH2:49]4)[cH:50][cH:51][c:52]3[F:53])[cH:54][n:55]2)[cH:56][cH:57]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[c:2])>>(O=[CH;D2;+0:1]-[c:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | e4209383939f49c0378a8859c2af8829f35179fef3a6302d2bd2297e | 1 | 1 | null | 567 |
429,894 | 1,835,473 | null | [H-].[Na+].[CH3:3][C@@H:4]([OH:7])[CH2:5][OH:6].F[C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:16]([CH3:34])=[N:17][CH:18]=[C:19]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH:20]=2)=[CH:11][C:10]=1[N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>CC(N(C)C)=O>[OH:7][C@H:4]([CH3:3])[CH2:5][O:6][C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:16]([CH3:34])=[N:17][CH:18]=[C:19]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[CH:24]=3)[CH:20]=2)=[CH:11][C:10]=1[N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1 | |f:0.1| | US20160038504A1_3040 | 2,016 | CC(=O)N(C)C.F[c:24]1[n:23][cH:22][c:21](-[c:20]2[c:2]([CH3:1])[n:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]3)[cH:19]2)[cH:37][c:30]1[N:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1.[H-].[Na+].[OH:25][CH2:26][C@@H:27]([CH3:28])[OH:29]>>[CH3:1][c:2]1[n:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]2)[cH:19][c:20]1-[c:21]1[cH:22][n:23][c:24]([O:25][CH2:26][C@@H:27]([CH3:28])[OH:29])[c:30]([N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[cH:37]1 | 0.266075 | CC(=O)N(C)C.C[C@@H](O)CO.Cc1ncc(NC(=O)c2cccc(C(F)(F)F)c2)cc1-c1cnc(F)c(N2CCOCC2)c1.[H-]~[Na+]>>Cc1ncc(NC(=O)c2cccc(C(F)(F)F)c2)cc1-c1cnc(OC[C@@H](C)O)c(N2CCOCC2)c1 | CC(=O)N(C)C.C[C@@H](O)CO.Cc1ncc(NC(=O)c2cccc(C(F)(F)F)c2)cc1-c1cnc(F)c(N2CCOCC2)c1.[H-].[Na+]>>Cc1ncc(NC(=O)c2cccc(C(F)(F)F)c2)cc1-c1cnc(OC[C@@H](C)O)c(N2CCOCC2)c1 | US20160038504A1_3040apps | 3d8996c12c8091ed4d440f29cc2a4d89581b6ea7b79cea06a0f432ea | CC(=O)N(C)C.F[c:24]1[n:23][cH:22][c:21](-[c:20]2[c:2]([CH3:1])[n:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]3)[cH:19]2)[cH:37][c:30]1[N:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1.[H-].[Na+].[OH:25][CH2:26][C@@H:27]([CH3:28])[OH:29] | [CH3:1][c:2]1[n:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]2)[cH:19][c:20]1-[c:21]1[cH:22][n:23][c:24]([O:25][CH2:26][C@@H:27]([CH3:28])[OH:29])[c:30]([N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[cH:37]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[O;H0;D2;+0:5]-[C:4])>>(F-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[OH;D1;+0:5]) | 4f4196eaedab9f578e0f926ce0f35097e0cee160f25356f5bf20e051 | 1 | 1 | CC(=O)N(C)C.[H-].[Na+] | 541 |
27,693 | 128,690 | 207,662 | [Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH2:16][CH2:17][F:18])[C:11]([CH3:19])=[N:10]2)=[C:4]([F:20])[CH:3]=1.[CH2:21](Br)[C:22]#[CH:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([O:8][CH2:23][C:22]#[CH:21])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH2:16][CH2:17][F:18])[C:11]([CH3:19])=[N:10]2)=[C:4]([F:20])[CH:3]=1 | |f:2.3.4| | US04906284_ | 1,990 | Br[CH2:3][C:2]#[CH:1].CC(C)=O.O=C([O-])[O-].[K+].[K+].[OH:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]([CH3:11])[n:12]([CH2:13][CH2:14][CH2:15][F:16])[c:17]2=[O:18])[c:19]([F:20])[cH:21][c:22]1[Cl:23]>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]([CH3:11])[n:12]([CH2:13][CH2:14][CH2:15][F:16])[c:17]2=[O:18])[c:19]([F:20])[cH:21][c:22]1[Cl:23] | 0.981367 | C#CCBr.CC(C)=O.Cc1nn(-c2cc(O)c(Cl)cc2F)c(=O)n1CCCF.O=C([O-])[O-]~[K+]~[K+]>>C#CCOc1cc(-n2nc(C)n(CCCF)c2=O)c(F)cc1Cl | C#CCBr.CC(C)=O.Cc1nn(-c2cc(O)c(Cl)cc2F)c(=O)n1CCCF.O=C([O-])[O-].[K+].[K+]>>C#CCOc1cc(-n2nc(C)n(CCCF)c2=O)c(F)cc1Cl | US04906284_grants | d0bca20f9891b0d20b46912deb3d8ae067078c487242d6d4905d8621 | Br[CH2:3][C:2]#[CH:1].CC(C)=O.O=C([O-])[O-].[K+].[K+].[OH:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]([CH3:11])[n:12]([CH2:13][CH2:14][CH2:15][F:16])[c:17]2=[O:18])[c:19]([F:20])[cH:21][c:22]1[Cl:23] | [CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[n:8]2[n:9][c:10]([CH3:11])[n:12]([CH2:13][CH2:14][CH2:15][F:16])[c:17]2=[O:18])[c:19]([F:20])[cH:21][c:22]1[Cl:23] | ([C;D1;H1:3]#[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5])>>(Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3]).([OH;D1;+0:4]-[c:5]) | 453079804e4903e3e1f939e654eef9c80f76da9eb6fc2297af45057e | 1 | 1 | CC(C)=O.O=C([O-])[O-].[K+].[K+] | 154 |
296,796 | 966,088 | 1,626,298 | [F:1][C:2]1[C:3]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:4][N:5]([C:7]2[N:28]=[CH:27][CH:26]=[CH:25][C:8]=2[C:9]([NH:11][CH:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]([OH:17])[C:14](O)=[O:15])=[O:10])[CH:6]=1.Cl.[CH3:36][O:37][NH2:38]>>[F:1][C:2]1[C:3]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:4][N:5]([C:7]2[N:28]=[CH:27][CH:26]=[CH:25][C:8]=2[C:9]([NH:11][CH:12]([CH:13]([OH:17])[C:14]([NH:38][O:37][CH3:36])=[O:15])[CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:10])[CH:6]=1 | |f:1.2| | US09051304B2_0457 | 2,015 | Cl.O[C:4](=[O:5])[CH:6]([OH:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][c:24]1-[n:25]1[cH:26][c:27]([F:28])[c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[n:36]1.[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[CH:6]([OH:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][c:24]1-[n:25]1[cH:26][c:27]([F:28])[c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[n:36]1 | 0.883014 | CON~Cl.O=C(NC(Cc1ccccc1)C(O)C(=O)O)c1cccnc1-n1cc(F)c(-c2ccccc2)n1>>CONC(=O)C(O)C(Cc1ccccc1)NC(=O)c1cccnc1-n1cc(F)c(-c2ccccc2)n1 | CON.Cl.O=C(NC(Cc1ccccc1)C(O)C(=O)O)c1cccnc1-n1cc(F)c(-c2ccccc2)n1>>CONC(=O)C(O)C(Cc1ccccc1)NC(=O)c1cccnc1-n1cc(F)c(-c2ccccc2)n1 | US09051304B2_0457grants | 06072c5c24a1ea724e506e5adff2109a2d7f7eba13adbf1cd1ff4f07 | Cl.O[C:4](=[O:5])[CH:6]([OH:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][c:24]1-[n:25]1[cH:26][c:27]([F:28])[c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[n:36]1.[CH3:1][O:2][NH2:3] | [CH3:1][O:2][NH:3][C:4](=[O:5])[CH:6]([OH:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][c:24]1-[n:25]1[cH:26][c:27]([F:28])[c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[n:36]1 | ([#8:4]-[NH;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]).([#8:4]-[NH2;D1;+0:5]) | bb17b2474db6567051c9e73388e21331add7eb7dbfcb74057fdc2fde | 1 | 1 | Cl | 480 |
224,462 | 753,097 | 1,240,657 | [N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]([OH:11])=O)=[CH:3][CH:2]=1.ON1C2C=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=N1.CN(C)CCCN=C=NCC.N1CCCC1>C(Cl)(Cl)Cl.ClCCl>[N:1]1[CH:2]=[CH:3][C:4](/[CH:7]=[CH:8]/[C:9]([N:15]2[CH2:16][CH2:21][CH2:20][CH2:19]2)=[O:11])=[CH:5][CH:6]=1 | null | US08288556B2_1186 | 2,012 | CCN=C=NCCCN(C)C.ClC(Cl)Cl.ClCCl.O[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1.On1nnc2ccccc21.[NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1>>[O:1]=[C:2](/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1 | 0.767419 | C1CCNC1.CCN=C=NCCCN(C)C.ClC(Cl)Cl.ClCCl.O=C(O)C=Cc1ccncc1.On1nnc2ccccc21>>O=C(/C=C/c1ccncc1)N1CCCC1 | C1CCNC1.CCN=C=NCCCN(C)C.ClC(Cl)Cl.ClCCl.O=C(O)C=Cc1ccncc1.On1nnc2ccccc21>>O=C(/C=C/c1ccncc1)N1CCCC1 | US08288556B2_1186grants | c93c756de02268dfbe5303f048467eb6567fb391e0f205e0f6d7221f | CCN=C=NCCCN(C)C.ClC(Cl)Cl.ClCCl.O[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1.On1nnc2ccccc21.[NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1 | [O:1]=[C:2](/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1 | ([C:5]-[N;H0;D3;+0:6](-[C:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | aa652d94b121d286aac4e204b5e4c42fbb5c1f75c74602b849eaeaab | 1 | 1 | CCN=C=NCCCN(C)C.ClC(Cl)Cl.ClCCl.On1nnc2ccccc21 | 517 |
357,762 | 593,404 | null | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[CH:13][C:12]=2[C:27]#[N:28])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:28][CH2:27][C:12]1[CH:13]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=2)[CH:15]=[CH:16][C:11]=1[NH:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1 | |f:1.2.3.4.5.6| | US20080176830A1_0383 | 2,008 | C1CCOC1.[Al+3].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]3)[cH:23][c:24]2[C:25]#[N:26])[cH:27][cH:28]1.[H-].[H-].[H-].[H-].[Li+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]3)[cH:23][c:24]2[CH2:25][NH2:26])[cH:27][cH:28]1 | 0.248944 | C1CCOC1.COc1ccc(CNc2ccc(-c3ccc(C(F)(F)F)cc3)cc2C#N)cc1.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>COc1ccc(CNc2ccc(-c3ccc(C(F)(F)F)cc3)cc2CN)cc1 | C1CCOC1.COc1ccc(CNc2ccc(-c3ccc(C(F)(F)F)cc3)cc2C#N)cc1.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>COc1ccc(CNc2ccc(-c3ccc(C(F)(F)F)cc3)cc2CN)cc1 | US20080176830A1_0383apps | 4258ac92434a1dd5274d6d996daa9d76c5e47b9c5e7b7b0849e448d4 | C1CCOC1.[Al+3].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]3)[cH:23][c:24]2[C:25]#[N:26])[cH:27][cH:28]1.[H-].[H-].[H-].[H-].[Li+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]3)[cH:23][c:24]2[CH2:25][NH2:26])[cH:27][cH:28]1 | ([NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3])>>([N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]) | 35e65afef8055e95e791906e7b199974efd87c632e3445dab6183229 | 1 | 1 | C1CCOC1.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 175 |
385,598 | 1,023,889 | null | F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>CN1C(=O)CCC1.O.C1(C)C=CC=CC=1>[F:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([O:32][C:29]2[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:31][CH:30]=2)[CH:9]=1)[C:5]#[N:6] | |f:1.2.3| | US20110059941A1_0486 | 2,011 | CN(C)C=O.CN1CCCC1=O.Cc1ccccc1.F[c:10]1[cH:11][c:12]([F:13])[cH:14][c:15]([C:16]#[N:17])[cH:18]1.O.O=C([O-])[O-].[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:19][cH:20]1.[K+].[K+]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][c:12]([F:13])[cH:14][c:15]([C:16]#[N:17])[cH:18]2)[cH:19][cH:20]1 | 0.40406 | CN(C)C=O.CN1CCCC1=O.CS(=O)(=O)c1ccc(O)cc1.Cc1ccccc1.N#Cc1cc(F)cc(F)c1.O.O=C([O-])[O-]~[K+]~[K+]>>CS(=O)(=O)c1ccc(Oc2cc(F)cc(C#N)c2)cc1 | CN(C)C=O.CN1CCCC1=O.CS(=O)(=O)c1ccc(O)cc1.Cc1ccccc1.N#Cc1cc(F)cc(F)c1.O.O=C([O-])[O-].[K+].[K+]>>CS(=O)(=O)c1ccc(Oc2cc(F)cc(C#N)c2)cc1 | US20110059941A1_0486apps | c713703f5c9ac74749857e7dfe78b9f5eb7e555aa496039d218211be | CN(C)C=O.CN1CCCC1=O.Cc1ccccc1.F[c:10]1[cH:11][c:12]([F:13])[cH:14][c:15]([C:16]#[N:17])[cH:18]1.O.O=C([O-])[O-].[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:19][cH:20]1.[K+].[K+] | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][c:12]([F:13])[cH:14][c:15]([C:16]#[N:17])[cH:18]2)[cH:19][cH:20]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 | CN(C)C=O.CN1CCCC1=O.Cc1ccccc1.O.O=C([O-])[O-].[K+].[K+] | 564 |
127,333 | 467,797 | 792,065 | [OH:1][CH2:2][C:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:30])[CH:13]([NH:17][CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[C:21]([F:29])[CH:22]=[C:23]([F:28])[CH:24]=3)[CH2:19]2)[CH2:14][CH2:15][CH3:16])=[N:8][N:7]=1)([CH3:5])[CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CS(C)=O>C(Cl)Cl>[CH3:4][C:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:30])[CH:13]([NH:17][CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[C:21]([F:29])[CH:22]=[C:23]([F:28])[CH:24]=3)[CH2:19]2)[CH2:14][CH2:15][CH3:16])=[N:8][N:7]=1)([CH3:5])[CH:2]=[O:1] | null | US07232820B2_0188 | 2,007 | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CS(C)=O.ClCCl.[CH3:1][CH2:2][CH2:3][CH:4]([NH:5][CH:6]1[CH2:7][CH2:8][c:9]2[cH:10][c:11]([F:12])[cH:13][c:14]([F:15])[c:16]2[CH2:17]1)[C:18](=[O:19])[NH:20][c:21]1[n:22][n:23][c:24]([C:25]([CH3:26])([CH3:27])[CH2:28][OH:29])[s:30]1>>[CH3:1][CH2:2][CH2:3][CH:4]([NH:5][CH:6]1[CH2:7][CH2:8][c:9]2[cH:10][c:11]([F:12])[cH:13][c:14]([F:15])[c:16]2[CH2:17]1)[C:18](=[O:19])[NH:20][c:21]1[n:22][n:23][c:24]([C:25]([CH3:26])([CH3:27])[CH:28]=[O:29])[s:30]1 | 0.678201 | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CCCC(NC1CCc2cc(F)cc(F)c2C1)C(=O)Nc1nnc(C(C)(C)CO)s1.CS(C)=O.ClCCl>>CCCC(NC1CCc2cc(F)cc(F)c2C1)C(=O)Nc1nnc(C(C)(C)C=O)s1 | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CCCC(NC1CCc2cc(F)cc(F)c2C1)C(=O)Nc1nnc(C(C)(C)CO)s1.CS(C)=O.ClCCl>>CCCC(NC1CCc2cc(F)cc(F)c2C1)C(=O)Nc1nnc(C(C)(C)C=O)s1 | US07232820B2_0188grants | 75210eede90ab13b0e6952cdcca348ae442646b008670c8b15a25b00 | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CS(C)=O.ClCCl.[CH3:1][CH2:2][CH2:3][CH:4]([NH:5][CH:6]1[CH2:7][CH2:8][c:9]2[cH:10][c:11]([F:12])[cH:13][c:14]([F:15])[c:16]2[CH2:17]1)[C:18](=[O:19])[NH:20][c:21]1[n:22][n:23][c:24]([C:25]([CH3:26])([CH3:27])[CH2:28][OH:29])[s:30]1 | [CH3:1][CH2:2][CH2:3][CH:4]([NH:5][CH:6]1[CH2:7][CH2:8][c:9]2[cH:10][c:11]([F:12])[cH:13][c:14]([F:15])[c:16]2[CH2:17]1)[C:18](=[O:19])[NH:20][c:21]1[n:22][n:23][c:24]([C:25]([CH3:26])([CH3:27])[CH:28]=[O:29])[s:30]1 | ([C:1]-[CH;D2;+0:2]=[O;H0;D1;+0:3])>>([C:1]-[CH2;D2;+0:2]-[OH;D1;+0:3]) | 61df3886a0291f08a9e9f8293588d04d916daa376a54f86534b439c2 | 1 | 1 | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.CS(C)=O.ClCCl | 142 |
130,950 | 478,240 | 806,627 | [F:1][C:2]([F:8])=[C:3]([CH3:7])[CH2:4][CH2:5][OH:6].[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C>O1CCCC1>[CH3:9][S:10]([O:6][CH2:5][CH2:4][C:3]([CH3:7])=[C:2]([F:8])[F:1])(=[O:12])=[O:11] | null | US07273878B2_0641 | 2,007 | C1CCOC1.CCN(CC)CC.Cl[S:6]([CH3:7])(=[O:8])=[O:9].[CH3:1][C:2]([CH2:3][CH2:4][OH:5])=[C:10]([F:11])[F:12]>>[CH3:1][C:2]([CH2:3][CH2:4][O:5][S:6]([CH3:7])(=[O:8])=[O:9])=[C:10]([F:11])[F:12] | 0.390628 | C1CCOC1.CC(CCO)=C(F)F.CCN(CC)CC.CS(=O)(=O)Cl>>CC(CCOS(C)(=O)=O)=C(F)F | C1CCOC1.CC(CCO)=C(F)F.CCN(CC)CC.CS(=O)(=O)Cl>>CC(CCOS(C)(=O)=O)=C(F)F | US07273878B2_0641grants | 885cdac282ec12eb96282693563ef048a24db3ef259ae58380af6243 | C1CCOC1.CCN(CC)CC.Cl[S:6]([CH3:7])(=[O:8])=[O:9].[CH3:1][C:2]([CH2:3][CH2:4][OH:5])=[C:10]([F:11])[F:12] | [CH3:1][C:2]([CH2:3][CH2:4][O:5][S:6]([CH3:7])(=[O:8])=[O:9])=[C:10]([F:11])[F:12] | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | C1CCOC1.CCN(CC)CC | 0 |
22,653 | 107,882 | 174,604 | [Cl:1][C:2]1[C:7]([O:8]C)=[CH:6][C:5]([N:10]2[C:14](=[O:15])[N:13]([CH:16]([F:18])[F:17])[C:12]([CH3:19])=[N:11]2)=[C:4]([F:20])[CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:10]2[C:14](=[O:15])[N:13]([CH:16]([F:17])[F:18])[C:12]([CH3:19])=[N:11]2)=[C:4]([F:20])[CH:3]=1 | null | US04743291_ | 1,988 | BrB(Br)Br.C[O:8][c:7]1[cH:6][c:5](-[n:4]2[n:3][c:2]([CH3:1])[n:16]([CH:17]([F:18])[F:19])[c:14]2=[O:15])[c:12]([F:13])[cH:11][c:9]1[Cl:10].ClCCl.O>>[CH3:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][c:7]([OH:8])[c:9]([Cl:10])[cH:11][c:12]2[F:13])[c:14](=[O:15])[n:16]1[CH:17]([F:18])[F:19] | 0.649956 | BrB(Br)Br.COc1cc(-n2nc(C)n(C(F)F)c2=O)c(F)cc1Cl.ClCCl.O>>Cc1nn(-c2cc(O)c(Cl)cc2F)c(=O)n1C(F)F | BrB(Br)Br.COc1cc(-n2nc(C)n(C(F)F)c2=O)c(F)cc1Cl.ClCCl.O>>Cc1nn(-c2cc(O)c(Cl)cc2F)c(=O)n1C(F)F | US04743291_grants | 923317f8b05a9761f34b4015716a59461a3a9f370e95db06139e93b8 | BrB(Br)Br.C[O:8][c:7]1[cH:6][c:5](-[n:4]2[n:3][c:2]([CH3:1])[n:16]([CH:17]([F:18])[F:19])[c:14]2=[O:15])[c:12]([F:13])[cH:11][c:9]1[Cl:10].ClCCl.O | [CH3:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][c:7]([OH:8])[c:9]([Cl:10])[cH:11][c:12]2[F:13])[c:14](=[O:15])[n:16]1[CH:17]([F:18])[F:19] | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | BrB(Br)Br.ClCCl.O | 48 |
223,615 | 750,124 | 1,234,924 | [CH2:1]([O:8][C:9]([N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:20][OH:21])[CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.[Cl-].[Na+].O>[CH2:1]([O:8][C:9]([N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:20][O:21][S:30]([CH3:29])(=[O:32])=[O:31])[CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | |f:3.4,7.8.9| | US08277807B2_1608 | 2,012 | C1CCOC1.CCN(CC)CC.CCOC(C)=O.Cl[S:2]([CH3:1])(=[O:3])=[O:4].O.O=C([O-])O.[Cl-].[Na+].[Na+].[OH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25]2>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25]2 | 0.475765 | C1CCOC1.CCN(CC)CC.CCOC(C)=O.CS(=O)(=O)Cl.O=C(OCc1ccccc1)N1Cc2ccc(CO)cc2C1.O=C([O-])O~[Na+].O~[Cl-]~[Na+]>>CS(=O)(=O)OCc1ccc2c(c1)CN(C(=O)OCc1ccccc1)C2 | C1CCOC1.CCN(CC)CC.CCOC(C)=O.CS(=O)(=O)Cl.O.O=C(OCc1ccccc1)N1Cc2ccc(CO)cc2C1.O=C([O-])O.[Cl-].[Na+].[Na+]>>CS(=O)(=O)OCc1ccc2c(c1)CN(C(=O)OCc1ccccc1)C2 | US08277807B2_1608grants | df0490c8c46951df0901f53462cf30d74ce7587727ad7dd16973b536 | C1CCOC1.CCN(CC)CC.CCOC(C)=O.Cl[S:2]([CH3:1])(=[O:3])=[O:4].O.O=C([O-])O.[Cl-].[Na+].[Na+].[OH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25]2 | [CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25]2 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | C1CCOC1.CCN(CC)CC.CCOC(C)=O.O.O=C([O-])O.[Cl-].[Na+].[Na+] | 0 |
279,617 | 915,996 | 1,532,168 | C(OC([N+](C(OC(C)C)=O)=[N-])=O)(C)C.[CH3:15][C:16]1([CH3:40])[O:20][CH:19]([CH2:21][N:22]2[C:34]3[C:33]4[CH:32]=[CH:31][C:30]([OH:35])=[CH:29][C:28]=4[N:27]=[CH:26][C:25]=3[N:24]=[C:23]2[CH2:36][O:37][CH2:38][CH3:39])[CH2:18][O:17]1.O[CH:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:15][C:16]1([CH3:40])[O:20][CH:19]([CH2:21][N:22]2[C:34]3[C:33]4[CH:32]=[CH:31][C:30]([O:35][CH:42]5[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]5)=[CH:29][C:28]=4[N:27]=[CH:26][C:25]=3[N:24]=[C:23]2[CH2:36][O:37][CH2:38][CH3:39])[CH2:18][O:17]1 | null | US08871782B2_1222 | 2,014 | C1CCOC1.CC(C)OC(=O)[N+](=[N-])C(=O)OC(C)C.O[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1.[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([OH:13])[cH:27][cH:28][c:29]3[c:30]2[n:31]1[CH2:32][CH:33]1[CH2:34][O:35][C:36]([CH3:37])([CH3:38])[O:39]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([O:13][CH:14]4[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]4)[cH:27][cH:28][c:29]3[c:30]2[n:31]1[CH2:32][CH:33]1[CH2:34][O:35][C:36]([CH3:37])([CH3:38])[O:39]1 | 0.249722 | C1CCOC1.CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)OC(=O)[N+](=[N-])C(=O)OC(C)C.CCOCc1nc2cnc3cc(O)ccc3c2n1CC1COC(C)(C)O1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CCOCc1nc2cnc3cc(OC4CCN(C(=O)OC(C)(C)C)CC4)ccc3c2n1CC1COC(C)(C)O1 | C1CCOC1.CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)OC(=O)[N+](=[N-])C(=O)OC(C)C.CCOCc1nc2cnc3cc(O)ccc3c2n1CC1COC(C)(C)O1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CCOCc1nc2cnc3cc(OC4CCN(C(=O)OC(C)(C)C)CC4)ccc3c2n1CC1COC(C)(C)O1 | US08871782B2_1222grants | b12e868ba0ce9d94c6c7f51c452eca425aa040b9e6b9fba183edb29b | C1CCOC1.CC(C)OC(=O)[N+](=[N-])C(=O)OC(C)C.O[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1.[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([OH:13])[cH:27][cH:28][c:29]3[c:30]2[n:31]1[CH2:32][CH:33]1[CH2:34][O:35][C:36]([CH3:37])([CH3:38])[O:39]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([O:13][CH:14]4[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]4)[cH:27][cH:28][c:29]3[c:30]2[n:31]1[CH2:32][CH:33]1[CH2:34][O:35][C:36]([CH3:37])([CH3:38])[O:39]1 | ([C:2]-[CH;D3;+0:1](-[C:3])-[O;H0;D2;+0:4]-[c:5])>>(O-[CH;D3;+0:1](-[C:2])-[C:3]).([OH;D1;+0:4]-[c:5]) | 43620c32f8b93f015b6fc9bd771a775fe633bcb65de62b65962f4ba1 | 1 | 1 | C1CCOC1.CC(C)OC(=O)[N+](=[N-])C(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 846 |
431,585 | 1,850,687 | null | [N+:1]([C:4]1[C:5]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][C:9]=1[NH2:10])([O-])=O.[NH4+].[Cl-]>CO.[Fe]>[N:6]1[CH:7]=[CH:8][C:9]([NH2:10])=[C:4]([NH2:1])[C:5]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1 | |f:1.2| | US20160068547A1_0872 | 2,016 | CO.O=[N+:14]([O-])[c:13]1[c:2]([NH2:1])[cH:3][cH:4][n:5][c:6]1-[c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1.[Cl-].[Fe].[NH4+]>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[c:13]1[NH2:14] | 0.955852 | CO.Nc1ccnc(-c2ccncc2)c1[N+](=O)[O-].[Cl-]~[NH4+].[Fe]>>Nc1ccnc(-c2ccncc2)c1N | CO.Nc1ccnc(-c2ccncc2)c1[N+](=O)[O-].[Cl-].[Fe].[NH4+]>>Nc1ccnc(-c2ccncc2)c1N | US20160068547A1_0872apps | 4160144aa8a49d6b39b8282c49d4dffcaeb5b9b14fe5f0d2bdd74320 | CO.O=[N+:14]([O-])[c:13]1[c:2]([NH2:1])[cH:3][cH:4][n:5][c:6]1-[c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1.[Cl-].[Fe].[NH4+] | [NH2:1][c:2]1[cH:3][cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[c:13]1[NH2:14] | ([#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 | CO.[Cl-].[Fe].[NH4+] | 269 |
272,590 | 894,075 | 1,490,927 | [C:1]([N:3]1[C:11]2[CH:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[C:5]2[CH2:13][N:14]([CH3:17])[CH2:15][CH2:16][C:4]1=2)#[CH:2].Br[C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][N:23]=[CH:24]2.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[CH:24]1[C:25]2[C:20](=[C:19]([C:2]#[C:1][N:3]3[C:11]4[CH:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=4[C:5]4[CH2:13][N:14]([CH3:17])[CH2:15][CH2:16][C:4]3=4)[CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:22][N:23]=1 | |f:2.3| | US08791132B2_1517 | 2,014 | Br[c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][n:19][cH:20][cH:21][c:22]12.CCCC[N+](CCCC)(CCCC)CCCC.O.[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[c:9]([n:10]2[C:11]#[CH:12])[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27]1.[F-]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[c:9]([n:10]2[C:11]#[C:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][n:19][cH:20][cH:21][c:22]23)[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27]1 | 0.966702 | Brc1cccc2cnccc12.C#Cn1c2c(c3cc(C)ccc31)CN(C)CC2.CCCC[N+](CCCC)(CCCC)CCCC~[F-].O>>Cc1ccc2c(c1)c1c(n2C#Cc2cccc3cnccc23)CCN(C)C1 | Brc1cccc2cnccc12.C#Cn1c2c(c3cc(C)ccc31)CN(C)CC2.CCCC[N+](CCCC)(CCCC)CCCC.O.[F-]>>Cc1ccc2c(c1)c1c(n2C#Cc2cccc3cnccc23)CCN(C)C1 | US08791132B2_1517grants | 6f00669ce4fa3183f68f1d21359028c8fd1eade85b4e088aea78211f | Br[c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][n:19][cH:20][cH:21][c:22]12.CCCC[N+](CCCC)(CCCC)CCCC.O.[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[c:9]([n:10]2[C:11]#[CH:12])[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27]1.[F-] | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[c:9]([n:10]2[C:11]#[C:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][n:19][cH:20][cH:21][c:22]23)[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27]1 | ([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 | CCCC[N+](CCCC)(CCCC)CCCC.O.[F-] | 659 |
434,908 | 1,871,940 | null | [F:1][C:2]1([F:17])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([OH:16])=O)[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.C(Cl)(=O)C(Cl)=O.[NH2:24][C@@H:25]1[CH2:30][CH2:29][O:28][C@@H:27]([C:31]2[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=2)[C:34]([O:36][CH3:37])=[O:35])[CH2:26]1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[F:17][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:24][C@@H:25]4[CH2:30][CH2:29][O:28][C@@H:27]([C:31]5[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=5)[C:34]([O:36][CH3:37])=[O:35])[CH2:26]4)=[O:16])[CH2:12][CH2:13]3)=[CH:10][C:4]=2[O:3]1 | null | US20160122331A1_1408 | 2,016 | CCN(CC)CC.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.O[C:14](=[O:15])[C:16]1([c:17]2[cH:18][cH:19][c:20]3[c:21]([cH:22]2)[O:23][C:24]([F:25])([F:26])[O:27]3)[CH2:28][CH2:29]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C@H:10]2[CH2:11][C@H:12]([NH2:13])[CH2:30][CH2:31][O:32]2)[cH:33]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C@H:10]2[CH2:11][C@H:12]([NH:13][C:14](=[O:15])[C:16]3([c:17]4[cH:18][cH:19][c:20]5[c:21]([cH:22]4)[O:23][C:24]([F:25])([F:26])[O:27]5)[CH2:28][CH2:29]3)[CH2:30][CH2:31][O:32]2)[cH:33]1 | 0.527377 | CCN(CC)CC.CN(C)C=O.COC(=O)c1cccc([C@H]2C[C@H](N)CCO2)c1.ClCCl.O=C(Cl)C(=O)Cl.O=C(O)C1(c2ccc3c(c2)OC(F)(F)O3)CC1>>COC(=O)c1cccc([C@H]2C[C@H](NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)CCO2)c1 | CCN(CC)CC.CN(C)C=O.COC(=O)c1cccc([C@H]2C[C@H](N)CCO2)c1.ClCCl.O=C(Cl)C(=O)Cl.O=C(O)C1(c2ccc3c(c2)OC(F)(F)O3)CC1>>COC(=O)c1cccc([C@H]2C[C@H](NC(=O)C3(c4ccc5c(c4)OC(F)(F)O5)CC3)CCO2)c1 | US20160122331A1_1408apps | 2f0215848350045cf606b25d52b4c8e848767c8c2b164284a8ac3fc9 | CCN(CC)CC.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.O[C:14](=[O:15])[C:16]1([c:17]2[cH:18][cH:19][c:20]3[c:21]([cH:22]2)[O:23][C:24]([F:25])([F:26])[O:27]3)[CH2:28][CH2:29]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C@H:10]2[CH2:11][C@H:12]([NH2:13])[CH2:30][CH2:31][O:32]2)[cH:33]1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C@H:10]2[CH2:11][C@H:12]([NH:13][C:14](=[O:15])[C:16]3([c:17]4[cH:18][cH:19][c:20]5[c:21]([cH:22]4)[O:23][C:24]([F:25])([F:26])[O:27]5)[CH2:28][CH2:29]3)[CH2:30][CH2:31][O:32]2)[cH:33]1 | ([C:4]-[NH;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]-[NH2;D1;+0:5]) | 9700dfbbea18932b10f40ed49527a6efd0b261364d0b5e3b1e240441 | 1 | 1 | CCN(CC)CC.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl | 230 |
130,238 | 476,108 | 803,467 | [CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([S:38][CH2:39][C:40]5[N:44]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:43]([S:49][CH2:50][CH3:51])=[N:42][N:41]=5)=[CH:34][CH:33]=4)=[O:30])=[CH:20][C:19]=3[CH:52]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:61])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:33]=[CH:34][C:35]([S:38]([CH2:39][C:40]5[N:44]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:43]([S:49][CH2:50][CH3:51])=[N:42][N:41]=5)=[O:61])=[CH:36][CH:37]=4)=[O:30])=[CH:20][C:19]=3[CH:52]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4] | |f:2.3.4| | US07262185B2_0859 | 2,007 | ClCCl.O=C(O[OH:29])c1cccc(Cl)c1.O=S([O-])([O-])=S.[CH3:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[CH:19]=[C:20]([C:21](=[O:22])[NH:23][c:24]2[cH:25][cH:26][c:27]([S:28][CH2:30][c:31]4[n:32][n:33][c:34]([S:35][CH2:36][CH3:37])[n:38]4[CH2:39][CH:40]([CH3:41])[CH3:42])[cH:43][cH:44]2)[CH2:45][CH2:46][N:47]3[CH2:48][CH:49]([CH3:50])[CH3:51])[cH:52][cH:53]1.[Na+].[Na+]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[CH:19]=[C:20]([C:21](=[O:22])[NH:23][c:24]2[cH:25][cH:26][c:27]([S:28](=[O:29])[CH2:30][c:31]4[n:32][n:33][c:34]([S:35][CH2:36][CH3:37])[n:38]4[CH2:39][CH:40]([CH3:41])[CH3:42])[cH:43][cH:44]2)[CH2:45][CH2:46][N:47]3[CH2:48][CH:49]([CH3:50])[CH3:51])[cH:52][cH:53]1 | 0.329493 | CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(SCc4nnc(SCC)n4CC(C)C)cc2)CCN3CC(C)C)cc1.ClCCl.O=C(OO)c1cccc(Cl)c1.O=S([O-])([O-])=S~[Na+]~[Na+]>>CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(S(=O)Cc4nnc(SCC)n4CC(C)C)cc2)CCN3CC(C)C)cc1 | CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(SCc4nnc(SCC)n4CC(C)C)cc2)CCN3CC(C)C)cc1.ClCCl.O=C(OO)c1cccc(Cl)c1.O=S([O-])([O-])=S.[Na+].[Na+]>>CCCCOCCOc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(S(=O)Cc4nnc(SCC)n4CC(C)C)cc2)CCN3CC(C)C)cc1 | US07262185B2_0859grants | 60a620ce58bb48fb5d21e84b0c1e6ff31841eb6a8541a703bcf40950 | ClCCl.O=C(O[OH:29])c1cccc(Cl)c1.O=S([O-])([O-])=S.[CH3:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[CH:19]=[C:20]([C:21](=[O:22])[NH:23][c:24]2[cH:25][cH:26][c:27]([S:28][CH2:30][c:31]4[n:32][n:33][c:34]([S:35][CH2:36][CH3:37])[n:38]4[CH2:39][CH:40]([CH3:41])[CH3:42])[cH:43][cH:44]2)[CH2:45][CH2:46][N:47]3[CH2:48][CH:49]([CH3:50])[CH3:51])[cH:52][cH:53]1.[Na+].[Na+] | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]3[c:17]([cH:18]2)[CH:19]=[C:20]([C:21](=[O:22])[NH:23][c:24]2[cH:25][cH:26][c:27]([S:28](=[O:29])[CH2:30][c:31]4[n:32][n:33][c:34]([S:35][CH2:36][CH3:37])[n:38]4[CH2:39][CH:40]([CH3:41])[CH3:42])[cH:43][cH:44]2)[CH2:45][CH2:46][N:47]3[CH2:48][CH:49]([CH3:50])[CH3:51])[cH:52][cH:53]1 | ([C:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4])>>(Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1).([C:2]-[S;H0;D2;+0:3]-[c:4]) | 3eca0f9955a304f24f0e70d3d79ae37309609db264458c56921bc8cd | 1 | 1 | ClCCl.O=S([O-])([O-])=S.[Na+].[Na+] | 500 |
297,351 | 967,587 | 1,628,868 | [N:1]1([C:6]2[N:11]=[C:10]([CH2:12][C:13]([O:15]C)=[O:14])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Li+]>C1COCC1>[N:1]1([C:6]2[N:11]=[C:10]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1 | |f:1.2| | US09056859B2_0642 | 2,015 | C1CCOC1.C[O:3][C:2](=[O:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][n:13][n:14]2)[n:15]1.[Li+].[OH-]>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][n:13][n:14]2)[n:15]1 | 0.942174 | C1CCOC1.COC(=O)Cc1cccc(-n2cnnn2)n1.[Li+]~[OH-]>>O=C(O)Cc1cccc(-n2cnnn2)n1 | C1CCOC1.COC(=O)Cc1cccc(-n2cnnn2)n1.[Li+].[OH-]>>O=C(O)Cc1cccc(-n2cnnn2)n1 | US09056859B2_0642grants | c6cf3882f24e9b301d2fd12687ed2feb2b16b47fdf073dea0a624a68 | C1CCOC1.C[O:3][C:2](=[O:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][n:13][n:14]2)[n:15]1.[Li+].[OH-] | [O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][n:13][n:14]2)[n:15]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 | C1CCOC1.[Li+].[OH-] | 88 |
289,848 | 944,406 | 1,585,064 | [Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[O:6].C(N(CC)C(C)C)(C)C.[CH3:21][O:22][CH2:23]Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[C:3]([O:11][CH2:21][O:22][CH3:23])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[O:6] | null | US08962674B2_0702 | 2,015 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)c1ccncc1.Cl.ClCCl.Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[CH:13]=[O:14]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[CH:13]=[O:14] | 0.971954 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)c1ccncc1.COCCl.Cl.ClCCl.O=Cc1cc(Cl)cc(Cl)c1O>>COCOc1c(Cl)cc(Cl)cc1C=O | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)c1ccncc1.COCCl.Cl.ClCCl.O=Cc1cc(Cl)cc(Cl)c1O>>COCOc1c(Cl)cc(Cl)cc1C=O | US08962674B2_0702grants | 6bb6f5d4051eb854cfaf97be3599bf4bf01f7834ddbe42f467496456 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)c1ccncc1.Cl.ClCCl.Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[CH:13]=[O:14] | [CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[CH:13]=[O:14] | ([#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(Cl-[CH2;D2;+0:1]-[#8:2]).([OH;D1;+0:3]-[c:4]) | fc6fab65fb339dbd7dfcd04c121911749ca2392ca0b8fedb59c018a1 | 1 | 1 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)c1ccncc1.Cl.ClCCl | 375 |
61,326 | 259,079 | 438,585 | [O:1]=[C:2]1[NH:7][C:6]2[C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([CH2:15][C:16]([OH:18])=O)[C:13]=3[CH2:14][C:5]=2[N:4]2[CH:19]=[CH:20][N:21]=[C:3]12.Cl.CN(C)CCCN=C=NCC.O[C:35]1[C:43]2N=N[NH:40][C:39]=2[CH:38]=[CH:37][CH:36]=1.NC1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O.Cl.O>[C:39]1([NH:40][C:16](=[O:18])[CH2:15][C:12]2[C:13]3[CH2:14][C:5]4[N:4]5[CH:19]=[CH:20][N:21]=[C:3]5[C:2](=[O:1])[NH:7][C:6]=4[C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH:43]=[CH:35][CH:36]=[CH:37][CH:38]=1 | |f:1.2,5.6| | US05902803_ | 1,999 | CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.O=C([O-])O.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[CH2:10][c:11]1[c:12]-2[nH:13][c:14](=[O:15])[c:16]2[n:17][cH:18][cH:19][n:20]12.Oc1cccc2[nH]nnc12.[NH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[Na+]>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[CH2:10][c:11]1[c:12]-2[nH:13][c:14](=[O:15])[c:16]2[n:17][cH:18][cH:19][n:20]12)[NH:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1 | 0.862343 | CCN=C=NCCCN(C)C~Cl.CN(C)C=O.Cl.Nc1ccccc1.O.O=C(O)Cc1cccc2c1Cc1c-2[nH]c(=O)c2nccn12.O=C([O-])O~[Na+].Oc1cccc2[nH]nnc12>>O=C(Cc1cccc2c1Cc1c-2[nH]c(=O)c2nccn12)Nc1ccccc1 | CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.Nc1ccccc1.O.O=C(O)Cc1cccc2c1Cc1c-2[nH]c(=O)c2nccn12.O=C([O-])O.Oc1cccc2[nH]nnc12.[Na+]>>O=C(Cc1cccc2c1Cc1c-2[nH]c(=O)c2nccn12)Nc1ccccc1 | US05902803_grants | f5de9c21823269ff4323384c06110188cdf7e86c23019b22108c6df4 | CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.O=C([O-])O.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[CH2:10][c:11]1[c:12]-2[nH:13][c:14](=[O:15])[c:16]2[n:17][cH:18][cH:19][n:20]12.Oc1cccc2[nH]nnc12.[NH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[Na+] | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[CH2:10][c:11]1[c:12]-2[nH:13][c:14](=[O:15])[c:16]2[n:17][cH:18][cH:19][n:20]12)[NH:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | 993a80a34f6acdc22e1630fbdadc440460d93877c75dd17e7db680f0 | 1 | 1 | CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.O=C([O-])O.Oc1cccc2[nH]nnc12.[Na+] | 365 |
82,395 | 331,463 | 563,937 | N1C=CC=CC=1.[NH2:7][C:8]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[CH2:17]([O:19][P:20]([CH2:25][C:26](Cl)=[O:27])(=[O:24])[O:21][CH2:22][CH3:23])[CH3:18]>C1(C)C=CC=CC=1>[CH2:22]([O:21][P:20]([CH2:25][C:26](=[O:27])[NH:7][C:8]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11])(=[O:24])[O:19][CH2:17][CH3:18])[CH3:23] | null | US06420386B1_ | 2,002 | Cc1ccccc1.Cl[C:7]([CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:19][CH2:20][CH3:21])=[O:8].[NH2:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]1[CH:17]=[O:18].c1ccncc1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][C:7](=[O:8])[NH:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]1[CH:17]=[O:18])[O:19][CH2:20][CH3:21] | 0.862636 | CCOP(=O)(CC(=O)Cl)OCC.Cc1ccccc1.Nc1cc(Cl)ccc1C=O.c1ccncc1>>CCOP(=O)(CC(=O)Nc1cc(Cl)ccc1C=O)OCC | CCOP(=O)(CC(=O)Cl)OCC.Cc1ccccc1.Nc1cc(Cl)ccc1C=O.c1ccncc1>>CCOP(=O)(CC(=O)Nc1cc(Cl)ccc1C=O)OCC | US06420386B1_grants | cf2c34b153812b4ebc08a0a91cd738920eb624f329b0bf6243bb9183 | Cc1ccccc1.Cl[C:7]([CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:19][CH2:20][CH3:21])=[O:8].[NH2:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]1[CH:17]=[O:18].c1ccncc1 | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][C:7](=[O:8])[NH:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]1[CH:17]=[O:18])[O:19][CH2:20][CH3:21] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | 3c2f9ebaf4afd5ac92b5ac7c3ff0ba51ecfcd4d148a3c3aad01989cb | 1 | 1 | Cc1ccccc1.c1ccncc1 | 9 |
219,109 | 736,325 | 1,213,008 | Br[Mg][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[C:13]1([C:19]2[C:28]([CH:29]=[O:30])=[C:27]([CH:31]([CH3:33])[CH3:32])[CH:26]=[C:25]3[C:20]=2[C:21](=[O:36])[CH2:22][C:23]([CH3:35])([CH3:34])[O:24]3)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:13]1([C:19]2[C:28]([CH:29]([OH:30])[C:3]3[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=3)=[C:27]([CH:31]([CH3:32])[CH3:33])[CH:26]=[C:25]3[C:20]=2[C:21](=[O:36])[CH2:22][C:23]([CH3:34])([CH3:35])[O:24]3)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1 | |f:2.3| | US08227511B2_0504 | 2,012 | Br[Mg][c:18]1[cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]1.C1CCOC1.O=C([O-])O.[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([c:8]([C:9]3=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]1[CH:16]=[O:17])[C:28](=[O:29])[CH2:30][C:31]([CH3:32])([CH3:33])[O:34]2.[Na+]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([c:8]([C:9]3=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]1[CH:16]([OH:17])[c:18]1[cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]1)[C:28](=[O:29])[CH2:30][C:31]([CH3:32])([CH3:33])[O:34]2 | 0.14287 | C1CCOC1.CC(C)c1cc2c(c(C3=CCCCC3)c1C=O)C(=O)CC(C)(C)O2.FC(F)(F)c1ccc([Mg]Br)cc1.O=C([O-])O~[Na+]>>CC(C)c1cc2c(c(C3=CCCCC3)c1C(O)c1ccc(C(F)(F)F)cc1)C(=O)CC(C)(C)O2 | C1CCOC1.CC(C)c1cc2c(c(C3=CCCCC3)c1C=O)C(=O)CC(C)(C)O2.FC(F)(F)c1ccc([Mg]Br)cc1.O=C([O-])O.[Na+]>>CC(C)c1cc2c(c(C3=CCCCC3)c1C(O)c1ccc(C(F)(F)F)cc1)C(=O)CC(C)(C)O2 | US08227511B2_0504grants | dcc7aa508dd6eb968ce8bbd86fef702821cc001658902d7c041e7906 | Br[Mg][c:18]1[cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]1.C1CCOC1.O=C([O-])O.[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([c:8]([C:9]3=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]1[CH:16]=[O:17])[C:28](=[O:29])[CH2:30][C:31]([CH3:32])([CH3:33])[O:34]2.[Na+] | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([c:8]([C:9]3=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15]1[CH:16]([OH:17])[c:18]1[cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]1)[C:28](=[O:29])[CH2:30][C:31]([CH3:32])([CH3:33])[O:34]2 | ([OH;D1;+0:4]-[CH;D3;+0:5](-[c:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[Mg]-[c;H0;D3;+0:1](:[c:2]):[c:3]).([O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6]) | 208d590b1b13f5d83224c2951149faab88b35b838d225abcf107a762 | 0.5 | 2 | C1CCOC1.O=C([O-])O.[Na+] | 309 |
361,359 | 636,835 | null | [N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH2:25])=[CH:19][CH:18]=1>>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH:25][C:12]([C:10]2[S:11][C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[CH:8][CH:9]=2)=[O:14])=[CH:19][CH:18]=1 | null | US20080293716A1_0401 | 2,008 | O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[s:22]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH2:9])[cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][n:19][cH:20][cH:21]3)[s:22]2)[cH:23][cH:24]1 | 0.798961 | COc1ccc(CCN)cc1.O=C(O)c1ccc(-c2ccncc2)s1>>COc1ccc(CCNC(=O)c2ccc(-c3ccncc3)s2)cc1 | COc1ccc(CCN)cc1.O=C(O)c1ccc(-c2ccncc2)s1>>COc1ccc(CCNC(=O)c2ccc(-c3ccncc3)s2)cc1 | US20080293716A1_0401apps | e3948f736a27e2984a601a5f2a3214f0e0c5087ff50a51e5c762c3a1 | O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[s:22]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH2:9])[cH:23][cH:24]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][n:19][cH:20][cH:21]3)[s:22]2)[cH:23][cH:24]1 | ([#16;a:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#16;a:4]).([C:5]-[NH2;D1;+0:6]) | 5bb56310c7e4f3afa8eb9f308cf2a936bbefe860ff713537ff3aa57d | 1 | 1 | null | 736 |
130,952 | 478,243 | 806,630 | CN(C)[CH:3]=[O:4].[O:6]=[C:7]([CH3:14])[CH2:8][CH2:9][CH2:10][C:11](O)=[O:12].C(=O)([O-])[O-].[K+].[K+].CI>O>[O:6]=[C:7]([CH3:14])[CH2:8][CH2:9][CH2:10][C:11]([O:4][CH3:3])=[O:12] | |f:2.3.4| | US07273878B2_0653 | 2,007 | CN(C)C=O.I[CH3:1].O.O=C([O-])[O-].[K+].[K+].[OH:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8]([CH3:9])=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8]([CH3:9])=[O:10] | 0.960077 | CC(=O)CCCC(=O)O.CI.CN(C)C=O.O.O=C([O-])[O-]~[K+]~[K+]>>COC(=O)CCCC(C)=O | CC(=O)CCCC(=O)O.CI.CN(C)C=O.O.O=C([O-])[O-].[K+].[K+]>>COC(=O)CCCC(C)=O | US07273878B2_0653grants | 12d458ee457b772b15b8d73c9dbd4d6c4358ab74450b3c9a6270267f | CN(C)C=O.I[CH3:1].O.O=C([O-])[O-].[K+].[K+].[OH:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8]([CH3:9])=[O:10] | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8]([CH3:9])=[O:10] | ([CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3]=[O;D1;H0:2])>>(I-[CH3;D1;+0:1]).([O;D1;H0:2]=[C:3]-[OH;D1;+0:4]) | c91e9563765e4a2f601b40326fcc9cfad1b5d00e212254922455906b | 1 | 1 | CN(C)C=O.O.O=C([O-])[O-].[K+].[K+] | 415 |
217,172 | 730,633 | 1,203,645 | [Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([F:26])[CH:20]=1)[CH3:16]>CC(C)=O>[CH2:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[C:21]([F:26])[CH:20]=1)[CH3:16] | |f:1.2.3,4.5| | US08202858B2_0310 | 2,012 | Br[CH2:11][CH2:12][CH2:13][CH2:14][Br:15].CC(C)=O.O=C([O-])[O-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:16]([F:17])[cH:18]1.[I-].[K+].[K+].[K+]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[c:16]([F:17])[cH:18]1 | 0.733959 | BrCCCCBr.CC(C)=O.CCOC(=O)c1ccc(O)c(F)c1.O=C([O-])[O-]~[K+]~[K+].[I-]~[K+]>>CCOC(=O)c1ccc(OCCCCBr)c(F)c1 | BrCCCCBr.CC(C)=O.CCOC(=O)c1ccc(O)c(F)c1.O=C([O-])[O-].[I-].[K+].[K+].[K+]>>CCOC(=O)c1ccc(OCCCCBr)c(F)c1 | US08202858B2_0310grants | 48e85a5aa9a33ddd7b43204c8244b6cebb8ceeed446b90c83240aa96 | Br[CH2:11][CH2:12][CH2:13][CH2:14][Br:15].CC(C)=O.O=C([O-])[O-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:16]([F:17])[cH:18]1.[I-].[K+].[K+].[K+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[c:16]([F:17])[cH:18]1 | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:10]1:[c:9]:[c:8]:[c:7](-[C:5](=[O;D1;H0:6])-[#8:4]-[C:3]):[c:13]:[c:12]:1)>>(Br-[CH2;D2;+0:1]-[C:2]).([C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]:[c:13]:1) | bf8199b7fc4d160a7c6a5a135fbc9cdd06237d1ce4b30f71a6cb6bc5 | 1 | 1 | CC(C)=O.O=C([O-])[O-].[I-].[K+].[K+].[K+] | 385 |
418,447 | 1,743,167 | null | [F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([OH:24])=[O:23])=[O:19])=[N:13]1>[Pd].CO>[NH2:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N:12]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[O:19])=[N:13]2)=[C:4]([F:11])[CH:5]=1 | null | US20150239847A1_0629 | 2,015 | CO.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[c:6](-[n:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[C:20](=[O:21])[OH:22])[n:23]2)[c:24]([F:25])[cH:26]1.[Pd]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6](-[n:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[C:20](=[O:21])[OH:22])[n:23]2)[c:24]([F:25])[cH:26]1 | 0.812672 | CO.O=C(O)c1ccccc1C(=O)Nc1ccn(-c2c(F)cc([N+](=O)[O-])cc2F)n1.[Pd]>>Nc1cc(F)c(-n2ccc(NC(=O)c3ccccc3C(=O)O)n2)c(F)c1 | CO.O=C(O)c1ccccc1C(=O)Nc1ccn(-c2c(F)cc([N+](=O)[O-])cc2F)n1.[Pd]>>Nc1cc(F)c(-n2ccc(NC(=O)c3ccccc3C(=O)O)n2)c(F)c1 | US20150239847A1_0629apps | 7c024815d9cc0c5645fe8d683d1d0e9d7cc3add35331012a5caeeb7f | CO.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[c:6](-[n:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[C:20](=[O:21])[OH:22])[n:23]2)[c:24]([F:25])[cH:26]1.[Pd] | [NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6](-[n:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[C:20](=[O:21])[OH:22])[n:23]2)[c:24]([F:25])[cH:26]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pd] | 1 |
29,112 | 134,395 | 216,627 | [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:15]([CH2:16][C:17]([OH:19])=O)[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=1.[C:20](N1C=CN=C1)([N:22]1C=CN=C1)=O.CN>O1CCCC1>[CH3:20][NH:22][C:17](=[O:19])[CH2:16][N:15]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1 | null | US04948800_ | 1,990 | C1CCOC1.O=C(n1ccnc1)n1ccnc1.O[C:3](=[O:4])[CH2:5][n:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[n:14][c:15]2[cH:16][cH:17][cH:18][n:19][c:20]12.[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][n:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[n:14][c:15]2[cH:16][cH:17][cH:18][n:19][c:20]12 | 0.833711 | C1CCOC1.CN.O=C(O)Cn1c(-c2ccccn2)nc2cccnc21.O=C(n1ccnc1)n1ccnc1>>CNC(=O)Cn1c(-c2ccccn2)nc2cccnc21 | C1CCOC1.CN.O=C(O)Cn1c(-c2ccccn2)nc2cccnc21.O=C(n1ccnc1)n1ccnc1>>CNC(=O)Cn1c(-c2ccccn2)nc2cccnc21 | US04948800_grants | 4754640ec45ff777db868774d7ec87d048384ffad60404b569be684f | C1CCOC1.O=C(n1ccnc1)n1ccnc1.O[C:3](=[O:4])[CH2:5][n:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[n:14][c:15]2[cH:16][cH:17][cH:18][n:19][c:20]12.[CH3:1][NH2:2] | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][n:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[n:14][c:15]2[cH:16][cH:17][cH:18][n:19][c:20]12 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:5]-[C;D1;H3:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C;D1;H3:4]-[NH2;D1;+0:5]) | 9700dfbbea18932b10f40ed49527a6efd0b261364d0b5e3b1e240441 | 1 | 1 | C1CCOC1.O=C(n1ccnc1)n1ccnc1 | 230 |
62,602 | 263,863 | 446,418 | [CH2:1]1[O:12][C:11]2[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][C:3]=2[O:2]1.[CH3:13][O:14][C:15](=[O:34])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[C:24](Cl)[C:25]3[C:30]([CH3:31])=[C:29]([CH3:32])[S:28][C:26]=3[N:27]=2)=[CH:18][CH:17]=1>>[CH3:13][O:14][C:15](=[O:34])[C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:23]=[C:24]([NH:8][CH2:7][CH2:6][C:5]3[CH:9]=[CH:10][C:11]4[O:12][CH2:1][O:2][C:3]=4[CH:4]=3)[C:25]3[C:30]([CH3:31])=[C:29]([CH3:32])[S:28][C:26]=3[N:27]=2)=[CH:20][CH:21]=1 | null | US05948911_ | 1,999 | Cl[c:11]1[n:10][c:9](-[c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:33][cH:32]2)[n:31][c:30]2[c:24]1[c:25]([CH3:26])[c:27]([CH3:28])[s:29]2.[NH2:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][c:18]2[c:19]([cH:20]1)[O:21][CH2:22][O:23]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]([NH:12][CH2:13][CH2:14][c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O:21][CH2:22][O:23]4)[c:24]3[c:25]([CH3:26])[c:27]([CH3:28])[s:29][c:30]3[n:31]2)[cH:32][cH:33]1 | 0.956477 | COC(=O)c1ccc(-c2nc(Cl)c3c(C)c(C)sc3n2)cc1.NCCc1ccc2c(c1)OCO2>>COC(=O)c1ccc(-c2nc(NCCc3ccc4c(c3)OCO4)c3c(C)c(C)sc3n2)cc1 | COC(=O)c1ccc(-c2nc(Cl)c3c(C)c(C)sc3n2)cc1.NCCc1ccc2c(c1)OCO2>>COC(=O)c1ccc(-c2nc(NCCc3ccc4c(c3)OCO4)c3c(C)c(C)sc3n2)cc1 | US05948911_grants | 8d0fbe2b3ce2480cb72f33f334854172198a0031bc6e289b6adaa8ea | Cl[c:11]1[n:10][c:9](-[c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:33][cH:32]2)[n:31][c:30]2[c:24]1[c:25]([CH3:26])[c:27]([CH3:28])[s:29]2.[NH2:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][c:18]2[c:19]([cH:20]1)[O:21][CH2:22][O:23]2 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]([NH:12][CH2:13][CH2:14][c:15]3[cH:16][cH:17][c:18]4[c:19]([cH:20]3)[O:21][CH2:22][O:23]4)[c:24]3[c:25]([CH3:26])[c:27]([CH3:28])[s:29][c:30]3[n:31]2)[cH:32][cH:33]1 | ([#16;a:5]:[c:4](:[#7;a:6]):[c:3]:[c;H0;D3;+0:1](:[#7;a:2])-[NH;D2;+0:8]-[C:7])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]:[c:4](:[#16;a:5]):[#7;a:6]).([C:7]-[NH2;D1;+0:8]) | 02123007fbe7eb8c5b6f6664e6212d1f2d4d5727f20f4dced4fc6433 | 1 | 1 | null | 723 |
327,767 | 1,063,495 | 1,805,467 | [NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N:19]1[N:23]=[CH:22][CH:21]=[N:20]1)=[O:11].Br[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=1>>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:1][CH2:2][C@@H:3]2[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]2[C:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[N:19]2[N:23]=[CH:22][CH:21]=[N:20]2)=[O:11])=[N:26][CH:27]=1 | null | US09440982B2_1458 | 2,016 | Br[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][n:30]1.[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]2-[n:16]2[n:17][cH:18][cH:19][n:20]2)[C@@H:21]1[CH2:22][NH2:23]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]2-[n:16]2[n:17][cH:18][cH:19][n:20]2)[C@@H:21]1[CH2:22][NH:23][c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][n:30]1 | 0.981948 | C[C@@H]1CCCN(C(=O)c2cc(F)ccc2-n2nccn2)[C@@H]1CN.Clc1ccc(Br)nc1>>C[C@@H]1CCCN(C(=O)c2cc(F)ccc2-n2nccn2)[C@@H]1CNc1ccc(Cl)cn1 | C[C@@H]1CCCN(C(=O)c2cc(F)ccc2-n2nccn2)[C@@H]1CN.Clc1ccc(Br)nc1>>C[C@@H]1CCCN(C(=O)c2cc(F)ccc2-n2nccn2)[C@@H]1CNc1ccc(Cl)cn1 | US09440982B2_1458grants | c8cca5e15c973cf0df7779e077074d4510cbf793c6fbf91bfd23752c | Br[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][n:30]1.[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]2-[n:16]2[n:17][cH:18][cH:19][n:20]2)[C@@H:21]1[CH2:22][NH2:23] | [CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]2-[n:16]2[n:17][cH:18][cH:19][n:20]2)[C@@H:21]1[CH2:22][NH:23][c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][n:30]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[NH;D2;+0:5]-[C:4])>>(Br-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH2;D1;+0:5]) | 1634083d37af8240483f1cb26a22fd442589c33bcd94641f618c8df2 | 1 | 1 | null | 715 |
123,767 | 456,610 | 773,734 | [NH2:1][C@H:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([C@H:9]2[CH2:14][CH2:13][C@@H:12]([N:15]=[N+:16]=[N-:17])[CH2:11][C@H:10]2[CH2:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:3]1=[O:28].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](O)=[O:35].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[N:15]([C@@H:12]1[CH2:13][CH2:14][C@H:9]([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@H:2]([NH:1][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][CH:39]=[C:31]([C:30]([F:29])([F:40])[F:41])[CH:32]=3)[C:3]2=[O:28])[C@H:10]([CH2:18][S:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:21])[CH2:11]1)=[N+:16]=[N-:17] | |f:2.3| | US07183270B2_0743 | 2,007 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F.O[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]1.[N-:1]=[N+:2]=[N:3][C@@H:4]1[CH2:5][CH2:6][C@H:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH2:14])[C:27]2=[O:28])[C@H:29]([CH2:30][S:31](=[O:32])(=[O:33])[c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[CH2:40]1>>[N-:1]=[N+:2]=[N:3][C@@H:4]1[CH2:5][CH2:6][C@H:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:14][C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]3)[C:27]2=[O:28])[C@H:29]([CH2:30][S:31](=[O:32])(=[O:33])[c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[CH2:40]1 | 0.149127 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.O=C(O)c1cccc(C(F)(F)F)c1.[N-]=[N+]=N[C@@H]1CC[C@H](N2CCCC[C@H](N)C2=O)[C@H](CS(=O)(=O)c2ccccc2)C1>>[N-]=[N+]=N[C@@H]1CC[C@H](N2CCCC[C@H](NC(=O)c3cccc(C(F)(F)F)c3)C2=O)[C@H](CS(=O)(=O)c2ccccc2)C1 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F.O=C(O)c1cccc(C(F)(F)F)c1.[N-]=[N+]=N[C@@H]1CC[C@H](N2CCCC[C@H](N)C2=O)[C@H](CS(=O)(=O)c2ccccc2)C1>>[N-]=[N+]=N[C@@H]1CC[C@H](N2CCCC[C@H](NC(=O)c3cccc(C(F)(F)F)c3)C2=O)[C@H](CS(=O)(=O)c2ccccc2)C1 | US07183270B2_0743grants | 075047f9818c6b480974226008a213d0499f78ee86f0a2650e64fef2 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F.O[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]1.[N-:1]=[N+:2]=[N:3][C@@H:4]1[CH2:5][CH2:6][C@H:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH2:14])[C:27]2=[O:28])[C@H:29]([CH2:30][S:31](=[O:32])(=[O:33])[c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[CH2:40]1 | [N-:1]=[N+:2]=[N:3][C@@H:4]1[CH2:5][CH2:6][C@H:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:14][C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]3)[C:27]2=[O:28])[C@H:29]([CH2:30][S:31](=[O:32])(=[O:33])[c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[CH2:40]1 | ([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH2;D1;+0:8]) | a562edb175ae9dd016739a5eacbeb363249479a63537f7cc6ef16f5a | 1 | 1 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F | 718 |
4,150 | 21,245 | 28,287 | [OH:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=1.CN(C)C=O.C[O-].[Na+].Cl.[CH3:26][N:27]([CH2:29][CH2:30]Cl)[CH3:28]>CCOCC>[CH3:26][N:27]([CH3:28])[CH2:29][CH2:30][O:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=1 | |f:2.3,4.5| | US04038396_ | 1,977 | CCOCC.CN(C)C=O.C[O-].Cl.Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[Na+].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[n:13][c:14]3[n:15][cH:16][cH:17][cH:18][c:19]3[o:20]2)[cH:21]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[n:13][c:14]3[n:15][cH:16][cH:17][cH:18][c:19]3[o:20]2)[cH:21]1 | 0.840188 | CCOCC.CN(C)C=O.CN(C)CCCl~Cl.C[O-]~[Na+].Oc1cccc(-c2nc3ncccc3o2)c1>>CN(C)CCOc1cccc(-c2nc3ncccc3o2)c1 | CCOCC.CN(C)C=O.CN(C)CCCl.C[O-].Cl.Oc1cccc(-c2nc3ncccc3o2)c1.[Na+]>>CN(C)CCOc1cccc(-c2nc3ncccc3o2)c1 | US04038396_grants | ad5479963c856b04a973a027b26461ed64c1f5aa5ddd978622f05691 | CCOCC.CN(C)C=O.C[O-].Cl.Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[Na+].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[n:13][c:14]3[n:15][cH:16][cH:17][cH:18][c:19]3[o:20]2)[cH:21]1 | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[n:13][c:14]3[n:15][cH:16][cH:17][cH:18][c:19]3[o:20]2)[cH:21]1 | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(Cl-[CH2;D2;+0:1]-[C:2]).([OH;D1;+0:3]-[c:4]) | 527560bc9018fea283f8e56075bc56b30679ebc551e8680bcfc16c9a | 1 | 1 | CCOCC.CN(C)C=O.C[O-].Cl.[Na+] | 74 |
226,692 | 759,552 | 1,251,204 | [CH3:1][O:2][C:3]1[C:12]([NH:13][C:14](=[O:18])OCC)=[N:11][C:10]2[C:5](=[CH:6][C:7]([CH3:20])=[C:8]([CH3:19])[CH:9]=2)[N:4]=1.[Br:21][C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1>>[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14]([N:31]2[CH2:30][CH2:29][N:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([Br:21])[CH:23]=3)[CH2:33][CH2:32]2)=[O:18])=[N:11][C:10]2[C:5](=[CH:6][C:7]([CH3:20])=[C:8]([CH3:19])[CH:9]=2)[N:4]=1 | null | US08314100B2_0272 | 2,012 | CCO[C:16]([NH:15][c:14]1[c:3]([O:2][CH3:1])[n:4][c:5]2[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[cH:11][c:12]2[n:13]1)=[O:17].[NH:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][cH:25][c:26]([Br:27])[cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][O:2][c:3]1[n:4][c:5]2[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[cH:11][c:12]2[n:13][c:14]1[NH:15][C:16](=[O:17])[N:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][cH:25][c:26]([Br:27])[cH:28]2)[CH2:29][CH2:30]1 | 0.740907 | Brc1cccc(N2CCNCC2)c1.CCOC(=O)Nc1nc2cc(C)c(C)cc2nc1OC>>COc1nc2cc(C)c(C)cc2nc1NC(=O)N1CCN(c2cccc(Br)c2)CC1 | Brc1cccc(N2CCNCC2)c1.CCOC(=O)Nc1nc2cc(C)c(C)cc2nc1OC>>COc1nc2cc(C)c(C)cc2nc1NC(=O)N1CCN(c2cccc(Br)c2)CC1 | US08314100B2_0272grants | 90e7c877b8ca92f8abf69e06d0c96ad77991f9c1fedb66b14c136516 | CCO[C:16]([NH:15][c:14]1[c:3]([O:2][CH3:1])[n:4][c:5]2[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[cH:11][c:12]2[n:13]1)=[O:17].[NH:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][cH:25][c:26]([Br:27])[cH:28]2)[CH2:29][CH2:30]1 | [CH3:1][O:2][c:3]1[n:4][c:5]2[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[cH:11][c:12]2[n:13][c:14]1[NH:15][C:16](=[O:17])[N:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][cH:25][c:26]([Br:27])[cH:28]2)[CH2:29][CH2:30]1 | ([#7:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(C-C-O-[C;H0;D3;+0:1](-[#7:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0ce405ae9f6740f12f87ad2b682774cf25f6af46d02f7b894c64c58b | 1 | 1 | null | 613 |
147,366 | 527,918 | 884,558 | [H-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:7][CH2:6]1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.O>C1(C)C=CC=CC=1>[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][O:3][CH2:4][CH:5]1[CH2:7][CH2:6]1 | |f:0.1| | US07498460B2_0554 | 2,009 | Br[CH2:5][CH2:4][CH2:3][CH2:2][Br:1].Cc1ccccc1.O.[H-].[Na+].[OH:6][CH2:7][CH:8]1[CH2:9][CH2:10]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH:8]1[CH2:9][CH2:10]1 | 0.762986 | BrCCCCBr.Cc1ccccc1.O.OCC1CC1.[H-]~[Na+]>>BrCCCCOCC1CC1 | BrCCCCBr.Cc1ccccc1.O.OCC1CC1.[H-].[Na+]>>BrCCCCOCC1CC1 | US07498460B2_0554grants | e3017a6c061897bfeb4885e86e5643e0fb9b81025b8cdd1126f8196e | Br[CH2:5][CH2:4][CH2:3][CH2:2][Br:1].Cc1ccccc1.O.[H-].[Na+].[OH:6][CH2:7][CH:8]1[CH2:9][CH2:10]1 | [Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH:8]1[CH2:9][CH2:10]1 | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[C:3])>>(Br-[CH2;D2;+0:1]-[C:2]).([C:3]-[OH;D1;+0:4]) | a4c3d230363503c3cdd0e8b3bb15c888472ef0fddbf2cfc06e03712b | 0.5 | 2 | Cc1ccccc1.O.[H-].[Na+] | 95 |
310,198 | 1,008,740 | 1,707,159 | [CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]1[C:24]([OH:25])=[CH:23][C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)=[C:21]([F:33])[CH:20]=1)[C:14](=[O:34])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][C:43]#[N:44].O>CN(C=O)C>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]1[CH:20]=[C:21]([F:33])[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)=[CH:23][C:24]=1[O:25][CH2:42][C:43]#[N:44])[C:14](=[O:34])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | |f:1.2.3| | US09212182B2_0618 | 2,015 | Br[CH2:3][C:2]#[N:1].CN(C)C=O.O.O=C([O-])[O-].[K+].[K+].[OH:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[cH:14]2)[c:15]([F:16])[cH:17][c:18]1-[n:19]1[c:20](=[O:21])[cH:22][cH:23][c:24]2[cH:25][c:26]([S:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[cH:35][cH:36][c:37]12>>[N:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[cH:14]2)[c:15]([F:16])[cH:17][c:18]1-[n:19]1[c:20](=[O:21])[cH:22][cH:23][c:24]2[cH:25][c:26]([S:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[cH:35][cH:36][c:37]12 | 0.922402 | CN(C)C=O.N#CCBr.O.O=C([O-])[O-]~[K+]~[K+].O=c1ccc2cc(SCc3ccccc3)ccc2n1-c1cc(F)c(-c2cccc(F)c2)cc1O>>N#CCOc1cc(-c2cccc(F)c2)c(F)cc1-n1c(=O)ccc2cc(SCc3ccccc3)ccc21 | CN(C)C=O.N#CCBr.O.O=C([O-])[O-].O=c1ccc2cc(SCc3ccccc3)ccc2n1-c1cc(F)c(-c2cccc(F)c2)cc1O.[K+].[K+]>>N#CCOc1cc(-c2cccc(F)c2)c(F)cc1-n1c(=O)ccc2cc(SCc3ccccc3)ccc21 | US09212182B2_0618grants | b15b6832c281700732138ff63872457f6cefd1cb2ed418f4ea2876a6 | Br[CH2:3][C:2]#[N:1].CN(C)C=O.O.O=C([O-])[O-].[K+].[K+].[OH:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[cH:14]2)[c:15]([F:16])[cH:17][c:18]1-[n:19]1[c:20](=[O:21])[cH:22][cH:23][c:24]2[cH:25][c:26]([S:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[cH:35][cH:36][c:37]12 | [N:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[cH:14]2)[c:15]([F:16])[cH:17][c:18]1-[n:19]1[c:20](=[O:21])[cH:22][cH:23][c:24]2[cH:25][c:26]([S:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[cH:35][cH:36][c:37]12 | ([N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5])>>(Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3]).([OH;D1;+0:4]-[c:5]) | c7c5926071d71377a7e12e3fbe40a5d5276131d814eb4c46b3d2c102 | 1 | 1 | CN(C)C=O.O.O=C([O-])[O-].[K+].[K+] | 802 |
295,717 | 962,885 | 1,619,503 | Cl.[CH3:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([SH:9])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[C:23]([Cl:24])=[C:22]([Cl:25])[CH:21]=[CH:20][C:19]=1[Cl:26].C(OCC)C>CN(C=O)C>[CH3:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([S:9][CH2:17][C:18]2[C:19]([Cl:26])=[CH:20][CH:21]=[C:22]([Cl:25])[C:23]=2[Cl:24])[N:4]=1 | |f:0.1,2.3.4| | US09040538B2_0370 | 2,015 | Br[CH2:8][c:9]1[c:10]([Cl:11])[cH:12][cH:13][c:14]([Cl:15])[c:16]1[Cl:17].CCOCC.CN(C)C=O.Cl.O=C([O-])[O-].[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([SH:7])[n:18]1.[K+].[K+]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([S:7][CH2:8][c:9]2[c:10]([Cl:11])[cH:12][cH:13][c:14]([Cl:15])[c:16]2[Cl:17])[n:18]1 | 0.938573 | CCOCC.CN(C)C=O.Cc1ccnc(S)n1~Cl.Clc1ccc(Cl)c(CBr)c1Cl.O=C([O-])[O-]~[K+]~[K+]>>Cc1ccnc(SCc2c(Cl)ccc(Cl)c2Cl)n1 | CCOCC.CN(C)C=O.Cc1ccnc(S)n1.Cl.Clc1ccc(Cl)c(CBr)c1Cl.O=C([O-])[O-].[K+].[K+]>>Cc1ccnc(SCc2c(Cl)ccc(Cl)c2Cl)n1 | US09040538B2_0370grants | dd9eaba0774b577ccd61d58282566642ae830e8bd39af7a10b8ca817 | Br[CH2:8][c:9]1[c:10]([Cl:11])[cH:12][cH:13][c:14]([Cl:15])[c:16]1[Cl:17].CCOCC.CN(C)C=O.Cl.O=C([O-])[O-].[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([SH:7])[n:18]1.[K+].[K+] | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([S:7][CH2:8][c:9]2[c:10]([Cl:11])[cH:12][cH:13][c:14]([Cl:15])[c:16]2[Cl:17])[n:18]1 | ([#7;a:3]:[c:4](:[#7;a:5])-[S;H0;D2;+0:6]-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([#7;a:3]:[c:4](:[#7;a:5])-[SH;D1;+0:6]) | f8770a92e64f7ef8445ff28321a95fe101c079ef87aed92fbdf22f6f | 1 | 1 | CCOCC.CN(C)C=O.Cl.O=C([O-])[O-].[K+].[K+] | 699 |
147,757 | 529,277 | 886,895 | [NH2:1][CH2:2][C@@H:3]([NH:21][C:22](=[O:34])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH:30]([CH3:32])[CH3:31])=[C:25]([Cl:33])[CH:24]=1)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]3[CH:20]=2)=[CH:7][CH:6]=1.[CH3:35][N:36]([CH3:41])[CH2:37][C:38](O)=[O:39]>>[Cl:33][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[O:29][CH:30]([CH3:32])[CH3:31])[C:22]([NH:21][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]3[CH:20]=2)=[CH:7][CH:6]=1)[CH2:2][NH:1][C:38](=[O:39])[CH2:37][N:36]([CH3:41])[CH3:35])=[O:34] | null | US07504413B2_0868 | 2,009 | O[C:17](=[O:18])[CH2:19][N:20]([CH3:21])[CH3:22].[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([CH2:13][C@@H:14]([CH2:15][NH2:16])[NH:23][C:24](=[O:25])[c:26]4[cH:27][cH:28][c:29]([O:30][CH:31]([CH3:32])[CH3:33])[c:34]([Cl:35])[cH:36]4)[cH:37][cH:38]3)[n:39][c:40]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([CH2:13][C@@H:14]([CH2:15][NH:16][C:17](=[O:18])[CH2:19][N:20]([CH3:21])[CH3:22])[NH:23][C:24](=[O:25])[c:26]4[cH:27][cH:28][c:29]([O:30][CH:31]([CH3:32])[CH3:33])[c:34]([Cl:35])[cH:36]4)[cH:37][cH:38]3)[n:39][c:40]12 | 0.541483 | CN(C)CC(=O)O.Cc1cccn2cc(-c3ccc(C[C@@H](CN)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12>>Cc1cccn2cc(-c3ccc(C[C@@H](CNC(=O)CN(C)C)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | CN(C)CC(=O)O.Cc1cccn2cc(-c3ccc(C[C@@H](CN)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12>>Cc1cccn2cc(-c3ccc(C[C@@H](CNC(=O)CN(C)C)NC(=O)c4ccc(OC(C)C)c(Cl)c4)cc3)nc12 | US07504413B2_0868grants | ebcb1f9b1424c78f12186ef4bd91347c6861fd4b2eee09324014ce03 | O[C:17](=[O:18])[CH2:19][N:20]([CH3:21])[CH3:22].[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([CH2:13][C@@H:14]([CH2:15][NH2:16])[NH:23][C:24](=[O:25])[c:26]4[cH:27][cH:28][c:29]([O:30][CH:31]([CH3:32])[CH3:33])[c:34]([Cl:35])[cH:36]4)[cH:37][cH:38]3)[n:39][c:40]12 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([CH2:13][C@@H:14]([CH2:15][NH:16][C:17](=[O:18])[CH2:19][N:20]([CH3:21])[CH3:22])[NH:23][C:24](=[O:25])[c:26]4[cH:27][cH:28][c:29]([O:30][CH:31]([CH3:32])[CH3:33])[c:34]([Cl:35])[cH:36]4)[cH:37][cH:38]3)[n:39][c:40]12 | ([C:4]-[NH;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]-[NH2;D1;+0:5]) | 9700dfbbea18932b10f40ed49527a6efd0b261364d0b5e3b1e240441 | 1 | 1 | null | 230 |
115,762 | 433,121 | 737,829 | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[C:12]1[N:17]2[N:18]=[C:19]([CH2:24][CH3:25])[C:20]([N+:21]([O-])=O)=[C:16]2[CH:15]=[CH:14][CH:13]=1.C(O)(=O)C>C(O)C.O.[Zn]>[CH3:11][O:10][C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C:12]1[N:17]2[N:18]=[C:19]([CH2:24][CH3:25])[C:20]([NH2:21])=[C:16]2[CH:15]=[CH:14][CH:13]=1 | null | US07091215B2_0509 | 2,006 | CC(=O)O.CCO.O.O=[N+:23]([O-])[c:22]1[c:3]([CH2:2][CH3:1])[n:4][n:5]2[c:6](-[c:7]3[c:8]([O:9][CH3:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]3[O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]21.[Zn]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([O:9][CH3:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]3[O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]2[c:22]1[NH2:23] | 0.865074 | CC(=O)O.CCO.CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1[N+](=O)[O-].O.[Zn]>>CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1N | CC(=O)O.CCO.CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1[N+](=O)[O-].O.[Zn]>>CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1N | US07091215B2_0509grants | 9f2be686fc7a13992db4ad9d0d3fdb965bfc91c9fe79dedeadf23c24 | CC(=O)O.CCO.O.O=[N+:23]([O-])[c:22]1[c:3]([CH2:2][CH3:1])[n:4][n:5]2[c:6](-[c:7]3[c:8]([O:9][CH3:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]3[O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]21.[Zn] | [CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([O:9][CH3:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]3[O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]2[c:22]1[NH2:23] | ([NH2;D1;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[#7;a:5]:[c:6]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[#7;a:4]:[#7;a:5]:[c:6]:1) | bece654e65ac1f37c15a45408df8a01ab37250629f4cb1b30c202cce | 1 | 1 | CC(=O)O.CCO.O.[Zn] | 628 |
144,573 | 518,857 | 869,732 | [Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][CH2:11][OH:12]>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:12][CH2:11][CH3:10])=[CH:4][CH:3]=1 | null | US07459480B2_0213 | 2,008 | Br[CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1.[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1 | 0.967852 | BrCc1ccc(Br)cc1.CCO>>CCOCc1ccc(Br)cc1 | BrCc1ccc(Br)cc1.CCO>>CCOCc1ccc(Br)cc1 | US07459480B2_0213grants | 09d3a761f7ec2e3c108303568e1c6d82e14e1705888990921bc0e986 | Br[CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1.[CH3:1][CH2:2][OH:3] | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1 | ([C:3]-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([C:3]-[OH;D1;+0:4]) | 701cdfdda3ad4b079558ae8f26ac582ff4b30dfe8686db2b01ac2d32 | 1 | 1 | null | 464 |
49,185 | 213,675 | 346,317 | [NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[N+:8]([C:11]1[CH:21]=[CH:20][C:14]([CH2:15][O:16][C:17](Cl)=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9]>[OH-].[Na+].CCOCC>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][O:16][C:17]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:18])=[CH:20][CH:21]=1)([O-:10])=[O:9] | |f:2.3| | US05559224_ | 1,996 | CCOCC.Cl[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1.[Na+].[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][NH2:7].[OH-]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1 | 0.893257 | CCOCC.NCCCC(=O)O.O=C(Cl)OCc1ccc([N+](=O)[O-])cc1.[Na+]~[OH-]>>O=C(O)CCCNC(=O)OCc1ccc([N+](=O)[O-])cc1 | CCOCC.NCCCC(=O)O.O=C(Cl)OCc1ccc([N+](=O)[O-])cc1.[Na+].[OH-]>>O=C(O)CCCNC(=O)OCc1ccc([N+](=O)[O-])cc1 | US05559224_grants | f6ad9e5fa8a4bdc77ecd2876bbe13276f9892bf70b95896ac89cef5c | CCOCC.Cl[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1.[Na+].[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][NH2:7].[OH-] | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1 | ([C:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1)>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1).([C:11]-[NH2;D1;+0:12]) | 0700d9a1d582b4bef1511f9fb181aa1e8ef062a6c336f391def96a74 | 1 | 1 | CCOCC.[Na+].[OH-] | 479 |
20,747 | 99,788 | 161,750 | [C:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[C:6]([CH2:19][CH2:20][CH3:21])[C:5]=1[OH:22])(=[O:3])[CH3:2].[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][CH2:31][CH2:32][NH2:33]>>[C:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:33][CH2:32][CH2:31][CH2:30][CH2:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)=[O:16])=[C:6]([CH2:19][CH2:20][CH3:21])[C:5]=1[OH:22])(=[O:3])[CH3:2] | null | US04672066_ | 1,987 | O[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][c:5]1[c:4]([CH2:3][CH2:2][CH3:1])[c:31]([OH:32])[c:27]([C:28]([CH3:29])=[O:30])[cH:26][cH:25]1)=[O:13].[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[cH:25][cH:26][c:27]([C:28]([CH3:29])=[O:30])[c:31]1[OH:32] | 0.924186 | CCCc1c(OCCCCCC(=O)O)ccc(C(C)=O)c1O.NCCCCc1ccccn1>>CCCc1c(OCCCCCC(=O)NCCCCc2ccccn2)ccc(C(C)=O)c1O | CCCc1c(OCCCCCC(=O)O)ccc(C(C)=O)c1O.NCCCCc1ccccn1>>CCCc1c(OCCCCCC(=O)NCCCCc2ccccn2)ccc(C(C)=O)c1O | US04672066_grants | eaaaaf5eb87954c017bbdcc75485910e82c5c7f4940b0b682bb3fc71 | O[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][c:5]1[c:4]([CH2:3][CH2:2][CH3:1])[c:31]([OH:32])[c:27]([C:28]([CH3:29])=[O:30])[cH:26][cH:25]1)=[O:13].[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1 | [CH3:1][CH2:2][CH2:3][c:4]1[c:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[cH:25][cH:26][c:27]([C:28]([CH3:29])=[O:30])[c:31]1[OH:32] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:5]-[C:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 9700dfbbea18932b10f40ed49527a6efd0b261364d0b5e3b1e240441 | 1 | 1 | null | 230 |
21,883 | 104,511 | 168,955 | Cl[C:2]1[N:3]=[C:4]([N:14]([CH3:22])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[N:11]=[CH:10][N:9]=[C:8]([S:12][CH3:13])[C:6]=2[N:7]=1.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CS(C)=O>[CH2:15]([N:14]([CH3:22])[C:4]1[C:5]2[N:11]=[CH:10][N:9]=[C:8]([S:12][CH3:13])[C:6]=2[N:7]=[C:2]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1 | null | US04714698_ | 1,987 | CS(C)=O.Cl[c:19]1[n:18][c:8]([N:9]([CH3:10])[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:7]2[n:6][cH:5][n:4][c:3]([S:2][CH3:1])[c:27]2[n:26]1.[NH:20]1[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[c:8]([N:9]([CH3:10])[CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[n:18][c:19]([N:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[n:26][c:27]12 | 0.458242 | C1CNCCN1.CS(C)=O.CSc1ncnc2c(N(C)Cc3ccccc3)nc(Cl)nc12>>CSc1ncnc2c(N(C)Cc3ccccc3)nc(N3CCNCC3)nc12 | C1CNCCN1.CS(C)=O.CSc1ncnc2c(N(C)Cc3ccccc3)nc(Cl)nc12>>CSc1ncnc2c(N(C)Cc3ccccc3)nc(N3CCNCC3)nc12 | US04714698_grants | 4e9c8ae1f20c51300ac4325e017b2dc8068250c7a145ffc9b276d1c0 | CS(C)=O.Cl[c:19]1[n:18][c:8]([N:9]([CH3:10])[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:7]2[n:6][cH:5][n:4][c:3]([S:2][CH3:1])[c:27]2[n:26]1.[NH:20]1[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]1 | [CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[c:8]([N:9]([CH3:10])[CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[n:18][c:19]([N:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[n:26][c:27]12 | ([#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 | CS(C)=O | 36 |
153,632 | 547,086 | 915,636 | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH2:14][CH2:15][CH3:16])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.Cl[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:34]([CH3:37])([CH3:36])[CH3:35])=[C:23]([C:25]2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=2[F:33])[CH:24]=1>>[CH3:37][C:34]([C:22]1[C:23]([C:25]2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=2[F:33])=[CH:24][C:19]([CH2:18][O:1][C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]([CH2:14][CH2:15][CH3:16])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)=[CH:20][CH:21]=1)([CH3:35])[CH3:36] | null | US07572934B2_0272 | 2,009 | Cl[CH2:15][c:16]1[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[c:24](-[c:25]2[cH:26][c:27]([O:28][CH3:29])[cH:30][cH:31][c:32]2[F:33])[cH:34]1.[CH3:1][CH2:2][CH2:3][C@@H:4]([CH2:5][C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:35][cH:36]1>>[CH3:1][CH2:2][CH2:3][C@@H:4]([CH2:5][C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[c:24](-[c:25]3[cH:26][c:27]([O:28][CH3:29])[cH:30][cH:31][c:32]3[F:33])[cH:34]2)[cH:35][cH:36]1 | 0.500943 | CCC[C@@H](CC(=O)OC)c1ccc(O)cc1.COc1ccc(F)c(-c2cc(CCl)ccc2C(C)(C)C)c1>>CCC[C@@H](CC(=O)OC)c1ccc(OCc2ccc(C(C)(C)C)c(-c3cc(OC)ccc3F)c2)cc1 | CCC[C@@H](CC(=O)OC)c1ccc(O)cc1.COc1ccc(F)c(-c2cc(CCl)ccc2C(C)(C)C)c1>>CCC[C@@H](CC(=O)OC)c1ccc(OCc2ccc(C(C)(C)C)c(-c3cc(OC)ccc3F)c2)cc1 | US07572934B2_0272grants | c8ff0d8d86915ebd513866a27f6121fab8c204a000febf711b1c9b2d | Cl[CH2:15][c:16]1[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[c:24](-[c:25]2[cH:26][c:27]([O:28][CH3:29])[cH:30][cH:31][c:32]2[F:33])[cH:34]1.[CH3:1][CH2:2][CH2:3][C@@H:4]([CH2:5][C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:35][cH:36]1 | [CH3:1][CH2:2][CH2:3][C@@H:4]([CH2:5][C:6](=[O:7])[O:8][CH3:9])[c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[c:24](-[c:25]3[cH:26][c:27]([O:28][CH3:29])[cH:30][cH:31][c:32]3[F:33])[cH:34]2)[cH:35][cH:36]1 | ([c:4]-[O;H0;D2;+0:3]-[CH2;D2;+0:1]-[c:2])>>(Cl-[CH2;D2;+0:1]-[c:2]).([OH;D1;+0:3]-[c:4]) | 19ecb0c449632e1a0d99fd6d4c00076fad1615ed07bc86df1499acb5 | 1 | 1 | null | 49 |
212,463 | 716,679 | 1,180,622 | [NH:1]([C:8](=[O:32])[CH:9]([C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:21][CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:1]([C:8](=[O:32])[CH:9]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:30][CH:31]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | null | US08158825B2_0595 | 2,012 | CC(C)(C)[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.ClCCl.O=C(O)C(F)(F)F>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1 | 0.478865 | CC(C)(C)OC(=O)c1ccc(C(C(=O)Nc2ccccc2)C(=O)Nc2ccccc2)cc1.ClCCl.O=C(O)C(F)(F)F>>O=C(O)c1ccc(C(C(=O)Nc2ccccc2)C(=O)Nc2ccccc2)cc1 | CC(C)(C)OC(=O)c1ccc(C(C(=O)Nc2ccccc2)C(=O)Nc2ccccc2)cc1.ClCCl.O=C(O)C(F)(F)F>>O=C(O)c1ccc(C(C(=O)Nc2ccccc2)C(=O)Nc2ccccc2)cc1 | US08158825B2_0595grants | 2e542ca2dfb84e507f30b2099ae3b39c30b018e8ec548e7abc62a99f | CC(C)(C)[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.ClCCl.O=C(O)C(F)(F)F | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 19099d615ac8e69cee786c921f9ac0f1b45fdfafec5366cce7c8840f | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 752 |
165,660 | 582,907 | 969,055 | [CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1 | |f:1.2| | US07696193B2_0306 | 2,010 | CCO.CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH2:14][CH2:15][N:16]([CH:17]1[CH2:18][CH2:19][CH2:20]1)[CH2:21][CH2:22]2.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH2:14][CH2:15][N:16]([CH:17]1[CH2:18][CH2:19][CH2:20]1)[CH2:21][CH2:22]2 | 0.928158 | CCO.CCOC(=O)CCCOc1ccc2c(c1)CCN(C1CCC1)CC2.[Na+]~[OH-]>>O=C(O)CCCOc1ccc2c(c1)CCN(C1CCC1)CC2 | CCO.CCOC(=O)CCCOc1ccc2c(c1)CCN(C1CCC1)CC2.[Na+].[OH-]>>O=C(O)CCCOc1ccc2c(c1)CCN(C1CCC1)CC2 | US07696193B2_0306grants | faba143f9a0025044a95f0d571350e5bbcd960298e4f38c9b967c461 | CCO.CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH2:14][CH2:15][N:16]([CH:17]1[CH2:18][CH2:19][CH2:20]1)[CH2:21][CH2:22]2.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH2:14][CH2:15][N:16]([CH:17]1[CH2:18][CH2:19][CH2:20]1)[CH2:21][CH2:22]2 | ([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 | CCO.[Na+].[OH-] | 7 |
195,279 | 669,588 | 1,107,059 | [CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:11])([F:12])[F:13] | null | US08008483B2_0255 | 2,011 | ClC(Cl)(Cl)Cl.O.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C1CCC(=O)N1[Br:8].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Br:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | 0.244223 | Cc1ccc(C#N)cc1C(F)(F)F.ClC(Cl)(Cl)Cl.O.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C1CCC(=O)N1Br>>N#Cc1ccc(CBr)c(C(F)(F)F)c1 | Cc1ccc(C#N)cc1C(F)(F)F.ClC(Cl)(Cl)Cl.O.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C1CCC(=O)N1Br>>N#Cc1ccc(CBr)c(C(F)(F)F)c1 | US08008483B2_0255grants | 47ad6093e501a38bf91680f5f7f3e32b90d9831475b78b0ff7aacf4b | ClC(Cl)(Cl)Cl.O.O=C(OOC(=O)c1ccccc1)c1ccccc1.O=C1CCC(=O)N1[Br:8].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Br:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]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 | ClC(Cl)(Cl)Cl.O.O=C(OOC(=O)c1ccccc1)c1ccccc1 | 29 |
401,665 | 1,420,466 | null | Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:24][CH2:23][C:14]3([O:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH3:22])[CH2:15]3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[CH:35][C:36]3[O:40][CH:39]=[CH:38][C:37]=3[CH:41]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CO.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].C(Cl)Cl>[O:40]1[C:36]2[CH:35]=[CH:34][C:33]([C:2]3[CH:3]=[CH:4][C:5]([S:8]([N:11]4[CH2:12][CH2:13][C:14]5([O:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH3:22])[CH2:15]5)[CH2:23][CH2:24]4)(=[O:10])=[O:9])=[CH:6][CH:7]=3)=[CH:41][C:37]=2[CH:38]=[CH:39]1 | |f:2.3.4,7.8.9.10.11| | US20130237535A1_0329 | 2,013 | Br[c:15]1[cH:14][cH:13][c:12]([S:9]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:4][N:3]([CH2:2][CH3:1])[C:31](=[O:32])[CH2:30][O:29]3)[CH2:28][CH2:27]2)(=[O:10])=[O:11])[cH:26][cH:25]1.C1COCCO1.CC1(C)OB([c:16]2[cH:17][cH:18][c:19]3[o:20][cH:21][cH:22][c:23]3[cH:24]2)OC1(C)C.CO.ClCCl.Cl[Pd]Cl.O=C([O-])[O-].[Fe+2].[K+].[K+].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1>>[CH3:1][CH2:2][N:3]1[CH2:4][C:5]2([CH2:6][CH2:7][N:8]([S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15](-[c:16]4[cH:17][cH:18][c:19]5[o:20][cH:21][cH:22][c:23]5[cH:24]4)[cH:25][cH:26]3)[CH2:27][CH2:28]2)[O:29][CH2:30][C:31]1=[O:32] | 0.50898 | C1COCCO1.CC1(C)OB(c2ccc3occc3c2)OC1(C)C.CCN1CC2(CCN(S(=O)(=O)c3ccc(Br)cc3)CC2)OCC1=O.CO.ClCCl~Cl[Pd]Cl~[Fe+2]~c1ccc(P(c2ccccc2)[c-]2cccc2)cc1~c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.O=C([O-])[O-]~[K+]~[K+]>>CCN1CC2(CCN(S(=O)(=O)c3ccc(-c4ccc5occc5c4)cc3)CC2)OCC1=O | C1COCCO1.CC1(C)OB(c2ccc3occc3c2)OC1(C)C.CCN1CC2(CCN(S(=O)(=O)c3ccc(Br)cc3)CC2)OCC1=O.CO.ClCCl.Cl[Pd]Cl.O=C([O-])[O-].[Fe+2].[K+].[K+].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1>>CCN1CC2(CCN(S(=O)(=O)c3ccc(-c4ccc5occc5c4)cc3)CC2)OCC1=O | US20130237535A1_0329apps | d307b42f73536eed62491c6a0fdc53bd86dc6e11840cb05245e1e8a9 | Br[c:15]1[cH:14][cH:13][c:12]([S:9]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:4][N:3]([CH2:2][CH3:1])[C:31](=[O:32])[CH2:30][O:29]3)[CH2:28][CH2:27]2)(=[O:10])=[O:11])[cH:26][cH:25]1.C1COCCO1.CC1(C)OB([c:16]2[cH:17][cH:18][c:19]3[o:20][cH:21][cH:22][c:23]3[cH:24]2)OC1(C)C.CO.ClCCl.Cl[Pd]Cl.O=C([O-])[O-].[Fe+2].[K+].[K+].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | [CH3:1][CH2:2][N:3]1[CH2:4][C:5]2([CH2:6][CH2:7][N:8]([S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15](-[c:16]4[cH:17][cH:18][c:19]5[o:20][cH:21][cH:22][c:23]5[cH:24]4)[cH:25][cH:26]3)[CH2:27][CH2:28]2)[O:29][CH2:30][C:31]1=[O:32] | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[c;H0;D3;+0:4](:[c:5]):[c:6])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(C-C1(-C)-O-B(-[c;H0;D3;+0:4](:[c:5]):[c:6])-O-C-1(-C)-C) | 9070cdd4fb6f1677ab91185ae4f4e0309f05412abddf79c11415d35f | 0.5 | 2 | C1COCCO1.CO.ClCCl.Cl[Pd]Cl.O=C([O-])[O-].[Fe+2].[K+].[K+].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | 933 |
102 | 494 | 509 | [Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][Br:11])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10] | |f:2.3.4.5| | US03931239_ | 1,976 | Cl.ClCCl.Cl[C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14].[Al+3].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:15]([Cl:16])[c:17]1[Cl:18].[Cl-].[Cl-].[Cl-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14])[c:15]([Cl:16])[c:17]1[Cl:18] | 0.989558 | COc1cccc(Cl)c1Cl.Cl.ClCCl.O=C(Cl)CCCCCBr.[Al+3]~[Cl-]~[Cl-]~[Cl-]>>COc1ccc(C(=O)CCCCCBr)c(Cl)c1Cl | COc1cccc(Cl)c1Cl.Cl.ClCCl.O=C(Cl)CCCCCBr.[Al+3].[Cl-].[Cl-].[Cl-]>>COc1ccc(C(=O)CCCCCBr)c(Cl)c1Cl | US03931239_grants | ccc3bbd839c242cae45aa93783d9c052d2fc7097cf1833cff501d0e3 | Cl.ClCCl.Cl[C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14].[Al+3].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:15]([Cl:16])[c:17]1[Cl:18].[Cl-].[Cl-].[Cl-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14])[c:15]([Cl:16])[c:17]1[Cl:18] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:5](:[c:4]):[c:6])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([c:4]:[cH;D2;+0:5]:[c:6]) | 6744b6da9ed990d9e04bc2e5cba97e24866326ef579e4c88e3392980 | 1 | 1 | Cl.ClCCl.[Al+3].[Cl-].[Cl-].[Cl-] | 31 |
317,492 | 1,031,373 | 1,745,668 | [OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([NH:9][C:10]([C:12]2[N:13]=[CH:14][O:15][C:16]=2[C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[O:11])[CH:6]=[N:5]1.CCN(CC)CC.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:41][C:31]1[CH:36]=[CH:35][C:34]([S:37]([O:1][CH2:2][CH2:3][N:4]2[CH:8]=[C:7]([NH:9][C:10]([C:12]3[N:13]=[CH:14][O:15][C:16]=3[C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)=[O:11])[CH:6]=[N:5]2)(=[O:39])=[O:38])=[CH:33][CH:32]=1 | null | US09303023B2_0575 | 2,016 | CCN(CC)CC.ClCCl.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:33][cH:32]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH2:11][n:12]1[cH:13][c:14]([NH:15][C:16](=[O:17])[c:18]2[n:19][cH:20][o:21][c:22]2-[c:23]2[cH:24][cH:25][cH:26][c:27]([CH3:28])[cH:29]2)[cH:30][n:31]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][n:12]2[cH:13][c:14]([NH:15][C:16](=[O:17])[c:18]3[n:19][cH:20][o:21][c:22]3-[c:23]3[cH:24][cH:25][cH:26][c:27]([CH3:28])[cH:29]3)[cH:30][n:31]2)[cH:32][cH:33]1 | 0.55023 | CCN(CC)CC.Cc1ccc(S(=O)(=O)Cl)cc1.Cc1cccc(-c2ocnc2C(=O)Nc2cnn(CCO)c2)c1.ClCCl>>Cc1ccc(S(=O)(=O)OCCn2cc(NC(=O)c3ncoc3-c3cccc(C)c3)cn2)cc1 | CCN(CC)CC.Cc1ccc(S(=O)(=O)Cl)cc1.Cc1cccc(-c2ocnc2C(=O)Nc2cnn(CCO)c2)c1.ClCCl>>Cc1ccc(S(=O)(=O)OCCn2cc(NC(=O)c3ncoc3-c3cccc(C)c3)cn2)cc1 | US09303023B2_0575grants | 2b0181b9db918840c904a58ac95f7442ee29f5404669763aa9e2e4dc | CCN(CC)CC.ClCCl.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:33][cH:32]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH2:11][n:12]1[cH:13][c:14]([NH:15][C:16](=[O:17])[c:18]2[n:19][cH:20][o:21][c:22]2-[c:23]2[cH:24][cH:25][cH:26][c:27]([CH3:28])[cH:29]2)[cH:30][n:31]1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][n:12]2[cH:13][c:14]([NH:15][C:16](=[O:17])[c:18]3[n:19][cH:20][o:21][c:22]3-[c:23]3[cH:24][cH:25][cH:26][c:27]([CH3:28])[cH:29]3)[cH:30][n:31]2)[cH:32][cH:33]1 | ([C:5]-[O;H0;D2;+0:6]-[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]).([C:5]-[OH;D1;+0:6]) | 2a680215c1c69f116045ff1696194ac3ca890d5406b0abc3856bedc8 | 1 | 1 | CCN(CC)CC.ClCCl | 197 |
207,581 | 703,508 | 1,158,751 | [CH:1]1([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=3)[CH2:11][CH:10]([C:22]([OH:24])=O)[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O[N:26]=[C:27]([NH2:31])[CH2:28][CH2:29][CH3:30]>>[CH:1]1([C:6]([N:8]2[CH2:9][CH:10]([C:22]3[O:24][N:31]=[C:27]([CH2:28][CH2:29][CH3:30])[N:26]=3)[CH2:11][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=3)[CH2:13]2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1 | null | US08119663B2_1533 | 2,012 | O=[C:7](O)[CH:8]1[CH2:9][CH:10]([c:11]2[cH:12][cH:13][c:14]([CH2:15][CH3:16])[cH:17][cH:18]2)[CH2:19][N:20]([C:21](=[O:22])[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:28]1.[CH3:1][CH2:2][CH2:3][C:4](=[N:5][OH:6])[NH2:29]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][o:6][c:7]([CH:8]2[CH2:9][CH:10]([c:11]3[cH:12][cH:13][c:14]([CH2:15][CH3:16])[cH:17][cH:18]3)[CH2:19][N:20]([C:21](=[O:22])[CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:28]2)[n:29]1 | 0.717924 | CCCC(N)=NO.CCc1ccc(C2CC(C(=O)O)CN(C(=O)C3CCCC3)C2)cc1>>CCCc1noc(C2CC(c3ccc(CC)cc3)CN(C(=O)C3CCCC3)C2)n1 | CCCC(N)=NO.CCc1ccc(C2CC(C(=O)O)CN(C(=O)C3CCCC3)C2)cc1>>CCCc1noc(C2CC(c3ccc(CC)cc3)CN(C(=O)C3CCCC3)C2)n1 | US08119663B2_1533grants | 63e787a996761d6207f144cca3e440b9fc7fec85ae9c6b50246b6d10 | O=[C:7](O)[CH:8]1[CH2:9][CH:10]([c:11]2[cH:12][cH:13][c:14]([CH2:15][CH3:16])[cH:17][cH:18]2)[CH2:19][N:20]([C:21](=[O:22])[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:28]1.[CH3:1][CH2:2][CH2:3][C:4](=[N:5][OH:6])[NH2:29] | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][o:6][c:7]([CH:8]2[CH2:9][CH:10]([c:11]3[cH:12][cH:13][c:14]([CH2:15][CH3:16])[cH:17][cH:18]3)[CH2:19][N:20]([C:21](=[O:22])[CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:28]2)[n:29]1 | ([C:3]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[c;H0;D3;+0:1](-[C:2]):[o;H0;D2;+0:7]:[n;H0;D2;+0:6]:1)>>(O-[C;H0;D3;+0:1](=O)-[C:2]).([C:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:5])=[N;H0;D2;+0:6]-[OH;D1;+0:7]) | 8d8cd0adafd12d737c88a33fdf09a0ca02b3501b9e40e0fcf1782773 | 1 | 1 | null | 728 |
78,627 | 318,335 | 539,676 | [O:1]1[C:5]2([CH2:10][CH2:9][S:8][CH2:7][CH:6]2[C:11]([O:13]C)=[O:12])[O:4][CH2:3][CH2:2]1.[OH-].[K+]>C(O)C>[O:4]1[C:5]2([CH2:10][CH2:9][S:8][CH2:7][CH:6]2[C:11]([OH:13])=[O:12])[O:1][CH2:2][CH2:3]1 | |f:1.2| | US06331640B1_ | 2,001 | CCO.C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][S:6][CH2:7][CH2:8][C:9]12[O:10][CH2:11][CH2:12][O:13]2.[K+].[OH-]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][S:6][CH2:7][CH2:8][C:9]12[O:10][CH2:11][CH2:12][O:13]2 | 0.919017 | CCO.COC(=O)C1CSCCC12OCCO2.[K+]~[OH-]>>O=C(O)C1CSCCC12OCCO2 | CCO.COC(=O)C1CSCCC12OCCO2.[K+].[OH-]>>O=C(O)C1CSCCC12OCCO2 | US06331640B1_grants | 82f48e9c53cb2a823764764d4576d7ef40cdb787af8987e7a7b763c2 | CCO.C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][S:6][CH2:7][CH2:8][C:9]12[O:10][CH2:11][CH2:12][O:13]2.[K+].[OH-] | [O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][S:6][CH2:7][CH2:8][C:9]12[O:10][CH2:11][CH2:12][O:13]2 | ([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 | CCO.[K+].[OH-] | 88 |
254,638 | 843,739 | 1,403,892 | C(OC([N:8]1[C:11]2([CH2:15][CH2:14][N:13]([C:16]3[C:17]4[CH:24]=[CH:23][NH:22][C:18]=4[N:19]=[CH:20][N:21]=3)[CH2:12]2)[CH:10]([CH3:25])[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.C(Cl)(Cl)Cl>CO>[CH3:25][CH:10]1[C:11]2([CH2:15][CH2:14][N:13]([C:16]3[C:17]4[CH:24]=[CH:23][NH:22][C:18]=4[N:19]=[CH:20][N:21]=3)[CH2:12]2)[NH:8][CH2:9]1 | |f:1.2| | US08609647B2_0571 | 2,013 | C1COCCO1.CC(C)(C)OC(=O)[N:4]1[CH2:3][CH:2]([CH3:1])[C:5]12[CH2:6][CH2:7][N:8]([c:9]1[n:10][cH:11][n:12][c:13]3[nH:14][cH:15][cH:16][c:17]13)[CH2:18]2.CO.Cl.ClC(Cl)Cl>>[CH3:1][CH:2]1[CH2:3][NH:4][C:5]12[CH2:6][CH2:7][N:8]([c:9]1[n:10][cH:11][n:12][c:13]3[nH:14][cH:15][cH:16][c:17]13)[CH2:18]2 | 0.987572 | C1COCCO1~Cl.CC1CN(C(=O)OC(C)(C)C)C12CCN(c1ncnc3[nH]ccc13)C2.CO.ClC(Cl)Cl>>CC1CNC12CCN(c1ncnc3[nH]ccc13)C2 | C1COCCO1.CC1CN(C(=O)OC(C)(C)C)C12CCN(c1ncnc3[nH]ccc13)C2.CO.Cl.ClC(Cl)Cl>>CC1CNC12CCN(c1ncnc3[nH]ccc13)C2 | US08609647B2_0571grants | c45657b3cfb7d1604576fe33449b46f0e48913415269200f91894804 | C1COCCO1.CC(C)(C)OC(=O)[N:4]1[CH2:3][CH:2]([CH3:1])[C:5]12[CH2:6][CH2:7][N:8]([c:9]1[n:10][cH:11][n:12][c:13]3[nH:14][cH:15][cH:16][c:17]13)[CH2:18]2.CO.Cl.ClC(Cl)Cl | [CH3:1][CH:2]1[CH2:3][NH:4][C:5]12[CH2:6][CH2:7][N:8]([c:9]1[n:10][cH:11][n:12][c:13]3[nH:14][cH:15][cH:16][c:17]13)[CH2:18]2 | ([C:2]-[NH;D2;+0:1]-[C:3])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C:3]) | 55396c1492cc3823f0701ef923544f9f4c1af584b69f4ce5650dc5ae | 1 | 1 | C1COCCO1.CO.Cl.ClC(Cl)Cl | 575 |
368,284 | 736,285 | null | CS(O[CH2:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:10]1=[C:22]([C:25]#[N:26])[C:23]#[N:24])(=O)=O.[CH:27]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[I-].[K+].O>O1CCOCC1>[CH:27]1([NH:33][CH2:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:10]2=[C:22]([C:25]#[N:26])[C:23]#[N:24])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1 | |f:2.3| | US20090181948A1_0540 | 2,009 | C1COCCO1.CS(=O)(=O)O[CH2:10][CH2:9][CH2:8][N:7]1[C:6](=[C:3]([C:2]#[N:1])[C:4]#[N:5])[N:20]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:19][CH2:18]1.O.[I-].[K+].[NH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[N:1]#[C:2][C:3]([C:4]#[N:5])=[C:6]1[N:7]([CH2:8][CH2:9][CH2:10][NH:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1 | 0.530187 | C1COCCO1.CS(=O)(=O)OCCCN1CCN(CCN2CCCCC2)C1=C(C#N)C#N.NC1CCCCC1.O.[I-]~[K+]>>N#CC(C#N)=C1N(CCCNC2CCCCC2)CCN1CCN1CCCCC1 | C1COCCO1.CS(=O)(=O)OCCCN1CCN(CCN2CCCCC2)C1=C(C#N)C#N.NC1CCCCC1.O.[I-].[K+]>>N#CC(C#N)=C1N(CCCNC2CCCCC2)CCN1CCN1CCCCC1 | US20090181948A1_0540apps | b848187c63b55cba5ba7bfa149c2d15fceb7d25498dc13ff93e188b9 | C1COCCO1.CS(=O)(=O)O[CH2:10][CH2:9][CH2:8][N:7]1[C:6](=[C:3]([C:2]#[N:1])[C:4]#[N:5])[N:20]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:19][CH2:18]1.O.[I-].[K+].[NH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1 | [N:1]#[C:2][C:3]([C:4]#[N:5])=[C:6]1[N:7]([CH2:8][CH2:9][CH2:10][NH:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1 | ([C:3]-[NH;D2;+0:4]-[CH2;D2;+0:1]-[C:2])>>(C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH2;D1;+0:4]) | 5d3f372ebe7d387fa8a56ae339e3ebd0e1fe4d5d65e66a40ff59a18e | 1 | 1 | C1COCCO1.O.[I-].[K+] | 559 |
210,224 | 711,252 | 1,171,639 | [NH:1]([C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[CH:4]=1)[NH2:2].[CH3:10][C:11](=O)[CH2:12][CH3:13]>C(O)C>[C:11](=[N:2][NH:1][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[CH:4]=1)([CH2:12][CH3:13])[CH3:10] | null | US08148529B2_0139 | 2,012 | CCO.O=[C:3]([CH2:2][CH3:1])[CH3:4].[NH2:5][NH:6][c:7]1[cH:8][cH:9][nH:10][c:11](=[O:12])[cH:13]1>>[CH3:1][CH2:2][C:3]([CH3:4])=[N:5][NH:6][c:7]1[cH:8][cH:9][nH:10][c:11](=[O:12])[cH:13]1 | 0.980978 | CCC(C)=O.CCO.NNc1cc[nH]c(=O)c1>>CCC(C)=NNc1cc[nH]c(=O)c1 | CCC(C)=O.CCO.NNc1cc[nH]c(=O)c1>>CCC(C)=NNc1cc[nH]c(=O)c1 | US08148529B2_0139grants | 6c0504b457ac3f4ccc7515c8fe1fbd174448ff09e891383a057ef794 | CCO.O=[C:3]([CH2:2][CH3:1])[CH3:4].[NH2:5][NH:6][c:7]1[cH:8][cH:9][nH:10][c:11](=[O:12])[cH:13]1 | [CH3:1][CH2:2][C:3]([CH3:4])=[N:5][NH:6][c:7]1[cH:8][cH:9][nH:10][c:11](=[O:12])[cH:13]1 | ([#7:4]-[N;H0;D2;+0:5]=[C;H0;D3;+0:1](-[C:2])-[C;D1;H3:3])>>(O=[C;H0;D3;+0:1](-[C:2])-[C;D1;H3:3]).([#7:4]-[NH2;D1;+0:5]) | 2fad773977dbddee34d3bbd255b8a605790296d34da56a02bbc4cd07 | 1 | 1 | CCO | 285 |
356,027 | 560,908 | null | [CH2:1]([O:3][C:4]([C:6]1[O:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=1[F:25])=[O:5])[CH3:2]>C(O)C.Cl.[Fe]>[CH2:1]([O:3][C:4]([C:6]1[O:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[F:25])=[O:5])[CH3:2] | null | US20080085886A1_0400 | 2,008 | CCO.Cl.O=[N+:20]([O-])[c:19]1[cH:18][cH:17][c:16]([O:15][c:14]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:7][c:8]3[cH:9][cH:10][n:11][cH:12][c:13]32)[c:22]([F:23])[cH:21]1.[Fe]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[o:7][c:8]2[cH:9][cH:10][n:11][cH:12][c:13]2[c:14]1[O:15][c:16]1[cH:17][cH:18][c:19]([NH2:20])[cH:21][c:22]1[F:23] | 0.980293 | CCO.CCOC(=O)c1oc2ccncc2c1Oc1ccc([N+](=O)[O-])cc1F.Cl.[Fe]>>CCOC(=O)c1oc2ccncc2c1Oc1ccc(N)cc1F | CCO.CCOC(=O)c1oc2ccncc2c1Oc1ccc([N+](=O)[O-])cc1F.Cl.[Fe]>>CCOC(=O)c1oc2ccncc2c1Oc1ccc(N)cc1F | US20080085886A1_0400apps | 45d4f6d3edfc69eda9bfa2d10920d265fea236092c44e94c8897f3eb | CCO.Cl.O=[N+:20]([O-])[c:19]1[cH:18][cH:17][c:16]([O:15][c:14]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:7][c:8]3[cH:9][cH:10][n:11][cH:12][c:13]32)[c:22]([F:23])[cH:21]1.[Fe] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[o:7][c:8]2[cH:9][cH:10][n:11][cH:12][c:13]2[c:14]1[O:15][c:16]1[cH:17][cH:18][c:19]([NH2:20])[cH:21][c:22]1[F:23] | ([NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[#8:6]-[c:7]):[c:8]:[c:9]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5](-[#8:6]-[c:7]):[c:8]:[c:9]:1) | 29ce6f8549b3eb39f0ff459e6dcee2e695f06f6055034d715c31e38e | 1 | 1 | CCO.Cl.[Fe] | 335 |
119,258 | 444,055 | 755,026 | [CH2:1]([NH:8][CH2:9][C@@H:10]([C:12]1[CH:23]=[CH:22][C:15]2[O:16][C:17]([CH3:21])([CH3:20])[O:18][CH2:19][C:14]=2[CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]([S:42]([NH2:45])(=[O:44])=[O:43])[CH:39]=[CH:40][CH:41]=1.C(N(CC)C(C)C)(C)C.C(#N)C>O.C(OCC)C>[CH2:1]([N:8]([CH2:9][C@@H:10]([C:12]1[CH:23]=[CH:22][C:15]2[O:16][C:17]([CH3:20])([CH3:21])[O:18][CH2:19][C:14]=2[CH:13]=1)[OH:11])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]([S:42]([NH2:45])(=[O:44])=[O:43])[CH:39]=[CH:40][CH:41]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | null | US07135600B2_0671 | 2,006 | Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][c:28]([S:29]([NH2:30])(=[O:31])=[O:32])[cH:33]1.CC#N.CCN(C(C)C)C(C)C.CCOCC.O.[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][c:6]2[cH:7][c:8]([C@@H:9]([OH:10])[CH2:11][NH:12][CH2:34][c:35]3[cH:36][cH:37][cH:38][cH:39][cH:40]3)[cH:41][cH:42][c:43]2[O:44]1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][c:6]2[cH:7][c:8]([C@@H:9]([OH:10])[CH2:11][N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][c:28]([S:29]([NH2:30])(=[O:31])=[O:32])[cH:33]3)[CH2:34][c:35]3[cH:36][cH:37][cH:38][cH:39][cH:40]3)[cH:41][cH:42][c:43]2[O:44]1 | 0.486904 | CC#N.CC1(C)OCc2cc([C@@H](O)CNCc3ccccc3)ccc2O1.CCN(C(C)C)C(C)C.CCOCC.NS(=O)(=O)c1cccc(CCCOCCCCCCCBr)c1.O>>CC1(C)OCc2cc([C@@H](O)CN(CCCCCCCOCCCc3cccc(S(N)(=O)=O)c3)Cc3ccccc3)ccc2O1 | CC#N.CC1(C)OCc2cc([C@@H](O)CNCc3ccccc3)ccc2O1.CCN(C(C)C)C(C)C.CCOCC.NS(=O)(=O)c1cccc(CCCOCCCCCCCBr)c1.O>>CC1(C)OCc2cc([C@@H](O)CN(CCCCCCCOCCCc3cccc(S(N)(=O)=O)c3)Cc3ccccc3)ccc2O1 | US07135600B2_0671grants | 60c7f03eefdec62dd4692f02eef5895a7baab1ecd1e81cc6184a82ad | Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][c:28]([S:29]([NH2:30])(=[O:31])=[O:32])[cH:33]1.CC#N.CCN(C(C)C)C(C)C.CCOCC.O.[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][c:6]2[cH:7][c:8]([C@@H:9]([OH:10])[CH2:11][NH:12][CH2:34][c:35]3[cH:36][cH:37][cH:38][cH:39][cH:40]3)[cH:41][cH:42][c:43]2[O:44]1 | [CH3:1][C:2]1([CH3:3])[O:4][CH2:5][c:6]2[cH:7][c:8]([C@@H:9]([OH:10])[CH2:11][N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][c:28]([S:29]([NH2:30])(=[O:31])=[O:32])[cH:33]3)[CH2:34][c:35]3[cH:36][cH:37][cH:38][cH:39][cH:40]3)[cH:41][cH:42][c:43]2[O:44]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])>>(Br-[CH2;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) | 8c9df7f4c910b7e7e5bda94f4a229eb328f6f7f5e6bd0c5fbb8cf97a | 0.5 | 2 | CC#N.CCN(C(C)C)C(C)C.CCOCC.O | 722 |
50,148 | 217,677 | 355,726 | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)=[C:19]([O:30][CH2:31][CH2:32][OH:33])[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:36][C:37]1[CH:38]=[N:39][C:40](Cl)=[N:41][CH:42]=1.[Cl-].[NH4+]>CC(N(C)C)=O>[Br:36][C:37]1[CH:38]=[N:39][C:40]([O:33][CH2:32][CH2:31][O:30][C:19]2[N:18]=[CH:17][N:16]=[C:15]([NH:14][S:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=3)(=[O:12])=[O:13])[C:20]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=2)=[N:41][CH:42]=1 | |f:1.2,4.5| | US05589478_ | 1,996 | CC(=O)N(C)C.Cl[c:33]1[n:34][cH:35][c:36]([Br:37])[cH:38][n:39]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27][c:28]2[O:29][CH2:30][CH2:31][OH:32])[cH:40]1.[Cl-].[H-].[NH4+].[Na+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27][c:28]2[O:29][CH2:30][CH2:31][O:32][c:33]2[n:34][cH:35][c:36]([Br:37])[cH:38][n:39]2)[cH:40]1 | 0.217455 | CC(=O)N(C)C.COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCO)c1.Clc1ncc(Br)cn1.[Cl-]~[NH4+].[H-]~[Na+]>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)c1 | CC(=O)N(C)C.COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCO)c1.Clc1ncc(Br)cn1.[Cl-].[H-].[NH4+].[Na+]>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)c1 | US05589478_grants | b928425097131f9726aa40e47b0c429359533a2fa31eabc6c17be985 | CC(=O)N(C)C.Cl[c:33]1[n:34][cH:35][c:36]([Br:37])[cH:38][n:39]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27][c:28]2[O:29][CH2:30][CH2:31][OH:32])[cH:40]1.[Cl-].[H-].[NH4+].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27][c:28]2[O:29][CH2:30][CH2:31][O:32][c:33]2[n:34][cH:35][c:36]([Br:37])[cH:38][n:39]2)[cH:40]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[O;H0;D2;+0:5]-[C:4])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C:4]-[OH;D1;+0:5]) | 5531dc961f1c71ad037df7257dccd8d3ba74ca7748378ce38ac5d4f5 | 1 | 1 | CC(=O)N(C)C.[Cl-].[H-].[NH4+].[Na+] | 37 |
372,193 | 803,786 | null | Br[CH2:2][CH2:3][CH2:4][OH:5].C([O-])(O)=O.[Na+].[C:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:13])[CH3:12]>C(Cl)Cl.[Cl-].[Na+].O>[C:11]([N:14]1[CH2:19][CH2:18][N:17]([CH2:2][CH2:3][CH2:4][OH:5])[CH2:16][CH2:15]1)(=[O:13])[CH3:12] | |f:1.2,5.6.7| | US20090306133A1_1488 | 2,009 | Br[CH2:8][CH2:9][CH2:10][OH:11].ClCCl.O.O=C([O-])O.[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:12][CH2:13]1.[Cl-].[Na+].[Na+]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:12][CH2:13]1 | 0.962488 | CC(=O)N1CCNCC1.ClCCl.O=C([O-])O~[Na+].OCCCBr.O~[Cl-]~[Na+]>>CC(=O)N1CCN(CCCO)CC1 | CC(=O)N1CCNCC1.ClCCl.O.O=C([O-])O.OCCCBr.[Cl-].[Na+].[Na+]>>CC(=O)N1CCN(CCCO)CC1 | US20090306133A1_1488apps | 038643056dcbc2820ff47796a95907d0d340f98d19f030e73f052b58 | Br[CH2:8][CH2:9][CH2:10][OH:11].ClCCl.O.O=C([O-])O.[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:12][CH2:13]1.[Cl-].[Na+].[Na+] | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:12][CH2:13]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]) | 53994dd2d8bb14288cdfb7c2951155e80ca49e2c98f7d531177a38b3 | 0.333333 | 3 | ClCCl.O.O=C([O-])O.[Cl-].[Na+].[Na+] | 73 |
208,591 | 706,169 | 1,163,995 | O[CH2:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[Br:34][CH2:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1 | null | US08129361B2_1451 | 2,012 | ClCCl.O=C1CCC(=O)N1[Br:1].O[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[Br:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21 | 0.934944 | ClCCl.O=C1CCC(=O)N1Br.OCCCC1CCCc2ccccc21.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>BrCCCC1CCCc2ccccc21 | ClCCl.O=C1CCC(=O)N1Br.OCCCC1CCCc2ccccc21.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>BrCCCC1CCCc2ccccc21 | US08129361B2_1451grants | 75349fb1194b2e48466ad6ee24e36bcbdd3f42b8eb62596488555e6e | ClCCl.O=C1CCC(=O)N1[Br:1].O[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [Br:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21 | ([Br;H0;D1;+0:3]-[CH2;D2;+0:1]-[C:2])>>(O-[CH2;D2;+0:1]-[C:2]).(O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:3]) | c57a8e388b4e9b41f471bbaa1af9e190f1153d143bc208d8ef03d27b | 1 | 1 | ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 581 |
259,988 | 859,141 | 1,429,153 | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]3[N:17]=[C:18]4[C:24]([C:25](O)=[O:26])=[CH:23][N:22]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:19]4=[N:20][CH:21]=3)=[N:7][N:8]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[C:4]([F:36])[CH:3]=1.F[B-](F)(F)F.[N:42]1(OC(N(C)C)=[N+](C)C)[C:46]2[CH:47]=CC=C[C:45]=2N=N1.C(N(CC)C(C)C)(C)C.C(N)(C)C>C(#N)C.C(OCC)(=O)C.O>[CH:46]([NH:42][C:25]([C:24]1[C:18]2[C:19](=[N:20][CH:21]=[C:16]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=4[F:36])[N:8]([CH2:11][CH2:12][N:13]([CH3:14])[CH3:15])[N:7]=3)[N:17]=2)[N:22]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:34])([CH3:35])[CH3:33])[CH:23]=1)=[O:26])([CH3:47])[CH3:45] | |f:1.2| | US08658646B2_1152 | 2,014 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.O.O[C:5](=[O:6])[c:7]1[cH:8][n:9]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[c:18]2[n:19][cH:20][c:21](-[c:22]3[n:23][n:24]([CH2:25][CH2:26][N:27]([CH3:28])[CH3:29])[c:30]4[cH:31][c:32]([Cl:33])[cH:34][c:35]([F:36])[c:37]34)[n:38][c:39]12.[CH3:1][CH:2]([CH3:3])[NH2:4]>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[c:7]1[cH:8][n:9]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[c:18]2[n:19][cH:20][c:21](-[c:22]3[n:23][n:24]([CH2:25][CH2:26][N:27]([CH3:28])[CH3:29])[c:30]4[cH:31][c:32]([Cl:33])[cH:34][c:35]([F:36])[c:37]34)[n:38][c:39]12 | 0.349206 | CC#N.CC(C)N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C~F[B-](F)(F)F.CN(C)CCn1nc(-c2cnc3c(n2)c(C(=O)O)cn3COCC[Si](C)(C)C)c2c(F)cc(Cl)cc21.O>>CC(C)NC(=O)c1cn(COCC[Si](C)(C)C)c2ncc(-c3nn(CCN(C)C)c4cc(Cl)cc(F)c34)nc12 | CC#N.CC(C)N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)CCn1nc(-c2cnc3c(n2)c(C(=O)O)cn3COCC[Si](C)(C)C)c2c(F)cc(Cl)cc21.F[B-](F)(F)F.O>>CC(C)NC(=O)c1cn(COCC[Si](C)(C)C)c2ncc(-c3nn(CCN(C)C)c4cc(Cl)cc(F)c34)nc12 | US08658646B2_1152grants | 76a7a1f7f5ffb5f4b01ca762d105db7fc5ce0763945729bd86e155fa | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.O.O[C:5](=[O:6])[c:7]1[cH:8][n:9]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[c:18]2[n:19][cH:20][c:21](-[c:22]3[n:23][n:24]([CH2:25][CH2:26][N:27]([CH3:28])[CH3:29])[c:30]4[cH:31][c:32]([Cl:33])[cH:34][c:35]([F:36])[c:37]34)[n:38][c:39]12.[CH3:1][CH:2]([CH3:3])[NH2:4] | [CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[c:7]1[cH:8][n:9]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[c:18]2[n:19][cH:20][c:21](-[c:22]3[n:23][n:24]([CH2:25][CH2:26][N:27]([CH3:28])[CH3:29])[c:30]4[cH:31][c:32]([Cl:33])[cH:34][c:35]([F:36])[c:37]34)[n:38][c:39]12 | ([#7;a:5]:[c:4]:[c:3](:[c:6]:[#7;a:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]:[#7;a:5]):[c:6]:[#7;a:7]).([C:8]-[NH2;D1;+0:9]) | 577a3840746a2ffc3bfb987e15784f8e92c2046a88743afbadcc1d3d | 1 | 1 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.O | 737 |
227,566 | 762,596 | 1,257,050 | [NH2:1][CH2:2][C:3]1[C:4]([NH:19][C@H:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH3:21])=[N:5][C:6]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)=[C:7]([F:9])[CH:8]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:53]=[C:54]1[NH:58][C@H:57]([C:59](O)=[O:60])[CH2:56][CH2:55]1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH:16]1([C:14]2[NH:13][N:12]=[C:11]([NH:10][C:6]3[N:5]=[C:4]([NH:19][C@H:20]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH3:21])[C:3]([CH2:2][NH:1][C:59]([C@@H:57]4[CH2:56][CH2:55][C:54](=[O:53])[NH:58]4)=[O:60])=[CH:8][C:7]=3[F:9])[CH:15]=2)[CH2:18][CH2:17]1 | |f:1.2| | US08324252B2_0494 | 2,012 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.ClCCl.F[P-](F)(F)(F)(F)F.O[C:22](=[O:23])[C@@H:24]1[CH2:25][CH2:26][C:27](=[O:28])[NH:29]1.[CH3:1][C@H:2]([NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[nH:14][n:15]2)[c:16]([F:17])[cH:18][c:19]1[CH2:20][NH2:21])[c:30]1[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]1>>[CH3:1][C@H:2]([NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[nH:14][n:15]2)[c:16]([F:17])[cH:18][c:19]1[CH2:20][NH:21][C:22](=[O:23])[C@@H:24]1[CH2:25][CH2:26][C:27](=[O:28])[NH:29]1)[c:30]1[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]1 | 0.848337 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.C[C@H](Nc1nc(Nc2cc(C3CC3)[nH]n2)c(F)cc1CN)c1ccc(F)cc1.ClCCl.O=C1CC[C@@H](C(=O)O)N1>>C[C@H](Nc1nc(Nc2cc(C3CC3)[nH]n2)c(F)cc1CNC(=O)[C@@H]1CCC(=O)N1)c1ccc(F)cc1 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.C[C@H](Nc1nc(Nc2cc(C3CC3)[nH]n2)c(F)cc1CN)c1ccc(F)cc1.ClCCl.F[P-](F)(F)(F)(F)F.O=C1CC[C@@H](C(=O)O)N1>>C[C@H](Nc1nc(Nc2cc(C3CC3)[nH]n2)c(F)cc1CNC(=O)[C@@H]1CCC(=O)N1)c1ccc(F)cc1 | US08324252B2_0494grants | 686986e6c397829cec0583b6c47c9bc0564f3f66e13ab20ee8d80475 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.ClCCl.F[P-](F)(F)(F)(F)F.O[C:22](=[O:23])[C@@H:24]1[CH2:25][CH2:26][C:27](=[O:28])[NH:29]1.[CH3:1][C@H:2]([NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[nH:14][n:15]2)[c:16]([F:17])[cH:18][c:19]1[CH2:20][NH2:21])[c:30]1[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]1 | [CH3:1][C@H:2]([NH:3][c:4]1[n:5][c:6]([NH:7][c:8]2[cH:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[nH:14][n:15]2)[c:16]([F:17])[cH:18][c:19]1[CH2:20][NH:21][C:22](=[O:23])[C@@H:24]1[CH2:25][CH2:26][C:27](=[O:28])[NH:29]1)[c:30]1[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]1 | ([#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]).([C:5]-[NH2;D1;+0:6]) | 72603df4e97d739310a00a91bf1cf924b7b460c6ce033fca82ac9cd9 | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.ClCCl.F[P-](F)(F)(F)(F)F | 216 |
295,419 | 961,880 | 1,618,000 | I[C:2]1[CH:18]=[CH:17][C:5]2[O:6][CH2:7][CH2:8][C:9]3[N:10]([N:11]=[C:12]([C:14]([NH2:16])=[O:15])[CH:13]=3)[C:4]=2[CH:3]=1.[C:19]([C:21]1([OH:27])[CH2:25][CH2:24][CH2:23][CH:22]1[F:26])#[CH:20]>>[F:26][CH:22]1[CH2:23][CH2:24][CH2:25][C:21]1([C:19]#[C:20][C:2]1[CH:18]=[CH:17][C:5]2[O:6][CH2:7][CH2:8][C:9]3[N:10]([N:11]=[C:12]([C:14]([NH2:16])=[O:15])[CH:13]=3)[C:4]=2[CH:3]=1)[OH:27] | null | US09034866B2_2349 | 2,015 | I[c:11]1[cH:10][c:9]2[c:23]([cH:22][cH:21]1)[O:24][CH2:25][CH2:26][c:6]1[cH:5][c:4]([C:2]([NH2:1])=[O:3])[n:8][n:7]1-2.[CH:12]#[C:13][C:14]1([OH:15])[CH2:16][CH2:17][CH2:18][CH:19]1[F:20]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[n:7]([n:8]1)-[c:9]1[cH:10][c:11]([C:12]#[C:13][C:14]3([OH:15])[CH2:16][CH2:17][CH2:18][CH:19]3[F:20])[cH:21][cH:22][c:23]1[O:24][CH2:25][CH2:26]2 | 0.992227 | C#CC1(O)CCCC1F.NC(=O)c1cc2n(n1)-c1cc(I)ccc1OCC2>>NC(=O)c1cc2n(n1)-c1cc(C#CC3(O)CCCC3F)ccc1OCC2 | C#CC1(O)CCCC1F.NC(=O)c1cc2n(n1)-c1cc(I)ccc1OCC2>>NC(=O)c1cc2n(n1)-c1cc(C#CC3(O)CCCC3F)ccc1OCC2 | US09034866B2_2349grants | 1c657afe3ed0ab69d095bd93124809efaddde9960725add6913477e5 | I[c:11]1[cH:10][c:9]2[c:23]([cH:22][cH:21]1)[O:24][CH2:25][CH2:26][c:6]1[cH:5][c:4]([C:2]([NH2:1])=[O:3])[n:8][n:7]1-2.[CH:12]#[C:13][C:14]1([OH:15])[CH2:16][CH2:17][CH2:18][CH:19]1[F:20] | [NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[n:7]([n:8]1)-[c:9]1[cH:10][c:11]([C:12]#[C:13][C:14]3([OH:15])[CH2:16][CH2:17][CH2:18][CH:19]3[F:20])[cH:21][cH:22][c:23]1[O:24][CH2:25][CH2:26]2 | ([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 |
277,439 | 909,646 | 1,519,307 | [NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[N:12]([C:19]([CH3:30])([CH3:29])[CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.[F:31][C:32]([F:44])([F:43])[C:33]1[CH:34]=[C:35]([CH2:39][C:40](O)=[O:41])[CH:36]=[CH:37][CH:38]=1.CCN(C(C)C)C(C)C>>[Si:22]([O:21][CH2:20][C:19]([N:12]1[C:13]2[N:14]=[CH:15][N:16]=[CH:17][C:18]=2[C:10]([C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:40](=[O:41])[CH2:39][C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([C:32]([F:43])([F:31])[F:44])[CH:34]=3)[CH:7]=[N:6][CH:5]=2)=[O:9])=[CH:11]1)([CH3:30])[CH3:29])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24] | null | US08846698B2_1203 | 2,014 | CCN(C(C)C)C(C)C.O[C:24](=[O:25])[CH2:26][c:27]1[cH:28][cH:29][cH:30][c:31]([C:32]([F:33])([F:34])[F:35])[cH:36]1.[CH3:1][C:2]([CH3:3])([CH2:4][O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[n:13]1[cH:14][c:15]([C:16](=[O:17])[c:18]2[cH:19][n:20][cH:21][c:22]([NH2:23])[cH:37]2)[c:38]2[cH:39][n:40][cH:41][n:42][c:43]12>>[CH3:1][C:2]([CH3:3])([CH2:4][O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[n:13]1[cH:14][c:15]([C:16](=[O:17])[c:18]2[cH:19][n:20][cH:21][c:22]([NH:23][C:24](=[O:25])[CH2:26][c:27]3[cH:28][cH:29][cH:30][c:31]([C:32]([F:33])([F:34])[F:35])[cH:36]3)[cH:37]2)[c:38]2[cH:39][n:40][cH:41][n:42][c:43]12 | 0.070903 | CC(C)(CO[Si](C)(C)C(C)(C)C)n1cc(C(=O)c2cncc(N)c2)c2cncnc21.CCN(C(C)C)C(C)C.O=C(O)Cc1cccc(C(F)(F)F)c1>>CC(C)(CO[Si](C)(C)C(C)(C)C)n1cc(C(=O)c2cncc(NC(=O)Cc3cccc(C(F)(F)F)c3)c2)c2cncnc21 | CC(C)(CO[Si](C)(C)C(C)(C)C)n1cc(C(=O)c2cncc(N)c2)c2cncnc21.CCN(C(C)C)C(C)C.O=C(O)Cc1cccc(C(F)(F)F)c1>>CC(C)(CO[Si](C)(C)C(C)(C)C)n1cc(C(=O)c2cncc(NC(=O)Cc3cccc(C(F)(F)F)c3)c2)c2cncnc21 | US08846698B2_1203grants | 0c2d35879c34e7b8d1d35496ae7cc8bfb7cf67399963f597818945d3 | CCN(C(C)C)C(C)C.O[C:24](=[O:25])[CH2:26][c:27]1[cH:28][cH:29][cH:30][c:31]([C:32]([F:33])([F:34])[F:35])[cH:36]1.[CH3:1][C:2]([CH3:3])([CH2:4][O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[n:13]1[cH:14][c:15]([C:16](=[O:17])[c:18]2[cH:19][n:20][cH:21][c:22]([NH2:23])[cH:37]2)[c:38]2[cH:39][n:40][cH:41][n:42][c:43]12 | [CH3:1][C:2]([CH3:3])([CH2:4][O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[n:13]1[cH:14][c:15]([C:16](=[O:17])[c:18]2[cH:19][n:20][cH:21][c:22]([NH:23][C:24](=[O:25])[CH2:26][c:27]3[cH:28][cH:29][cH:30][c:31]([C:32]([F:33])([F:34])[F:35])[cH:36]3)[cH:37]2)[c:38]2[cH:39][n:40][cH:41][n:42][c:43]12 | ([#7;a:4]:[c: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]:[c:5]:[c:6]-[NH2;D1;+0:7]) | 71bcfd4fef22bdbeaca4a631ecf90066289c7ecc34e85dce40672dbe | 1 | 1 | CCN(C(C)C)C(C)C | 724 |
321,728 | 1,045,953 | 1,774,622 | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O=S(Cl)Cl.C(Cl)Cl>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:19][CH:18]=1 | |f:1.2.3.4| | US09370522B2_0359 | 2,016 | ClCCl.O=S(Cl)Cl.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1.[Al+3].[Cl-].[Cl-].[Cl-].[cH:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1 | 0.486137 | ClCCl.Fc1ccccc1.O=C(O)Cc1ccc(F)cc1.O=S(Cl)Cl.[Al+3]~[Cl-]~[Cl-]~[Cl-]>>O=C(Cc1ccc(F)cc1)c1ccc(F)cc1 | ClCCl.Fc1ccccc1.O=C(O)Cc1ccc(F)cc1.O=S(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>>O=C(Cc1ccc(F)cc1)c1ccc(F)cc1 | US09370522B2_0359grants | 5ebe86d5b988ac72a3b21957e47dd6f59da50ba9ad38d66c00113863 | ClCCl.O=S(Cl)Cl.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1.[Al+3].[Cl-].[Cl-].[Cl-].[cH:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1 | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:5](:[c:4]):[c:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([c:4]:[cH;D2;+0:5]:[c:6]) | 6b61173e5c75ff6409a7862fd7eb803f9aa0b57b0e9b8cc2cf6a75dd | 1 | 1 | ClCCl.O=S(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-] | 435 |
333,771 | 174,028 | null | [NH2:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)[CH2:3][OH:4].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[CH2:13]([NH:1][C@@H:2]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([I:12])=[CH:10][CH:11]=1)[CH2:3][OH:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1 | null | US20040138462A1_0888 | 2,004 | ClCCl.O=[CH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1)[NH2:12]>>[OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1)[NH:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | 0.939182 | ClCCl.N[C@H](CO)Cc1ccc(I)cc1.O=Cc1ccccc1>>OC[C@H](Cc1ccc(I)cc1)NCc1ccccc1 | ClCCl.N[C@H](CO)Cc1ccc(I)cc1.O=Cc1ccccc1>>OC[C@H](Cc1ccc(I)cc1)NCc1ccccc1 | US20040138462A1_0888apps | fe17ffb2829d5989c4c21ea6020eab28641beb08c5dd6c5989785318 | ClCCl.O=[CH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1)[NH2:12] | [OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1)[NH:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | ([C:3]-[NH;D2;+0:4]-[CH2;D2;+0:1]-[c:2])>>(O=[CH;D2;+0:1]-[c:2]).([C:3]-[NH2;D1;+0:4]) | f78624bd87f224b709b14a27d6ee712af84642974d7873cf47c74b30 | 1 | 1 | ClCCl | 468 |
26,191 | 122,634 | 198,401 | [CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17](OCC)=[O:18])=[C:4]2[CH2:3]1.[BH4-].[Li+].Cl.N>O1CCCC1.O>[OH:18][CH2:17][C:16]1[N:15]=[CH:14][N:5]2[C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=3[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][C:4]=12 | |f:1.2| | US04863920_ | 1,989 | C1CCOC1.CCO[C:6]([c:5]1[c:4]2[n:10]([cH:9][n:8]1)-[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17](=[O:18])[N:2]([CH3:1])[CH2:3]2)=[O:7].Cl.N.O.[BH4-].[Li+]>>[CH3:1][N:2]1[CH2:3][c:4]2[c:5]([CH2:6][OH:7])[n:8][cH:9][n:10]2-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]1=[O:18] | 0.937769 | C1CCOC1.CCOC(=O)c1ncn2c1CN(C)C(=O)c1ccccc1-2.Cl.N.O.[BH4-]~[Li+]>>CN1Cc2c(CO)ncn2-c2ccccc2C1=O | C1CCOC1.CCOC(=O)c1ncn2c1CN(C)C(=O)c1ccccc1-2.Cl.N.O.[BH4-].[Li+]>>CN1Cc2c(CO)ncn2-c2ccccc2C1=O | US04863920_grants | 57a2d5be3bd4a2293724d9efd22e29dd90f9ad473fa6a517e674d7fb | C1CCOC1.CCO[C:6]([c:5]1[c:4]2[n:10]([cH:9][n:8]1)-[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17](=[O:18])[N:2]([CH3:1])[CH2:3]2)=[O:7].Cl.N.O.[BH4-].[Li+] | [CH3:1][N:2]1[CH2:3][c:4]2[c:5]([CH2:6][OH:7])[n:8][cH:9][n:10]2-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]1=[O:18] | ([#7;a:6]:[c:5]:[c:3](:[#7;a:4])-[CH2;D2;+0:1]-[OH;D1;+0:2])>>(C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[#7;a:4]):[c:5]:[#7;a:6]) | 747119a5f6af37e8a923e9f26594823425b62199d548727b8dfde1a2 | 1 | 1 | C1CCOC1.Cl.N.O.[BH4-].[Li+] | 286 |
28,895 | 133,455 | 215,129 | [CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:34])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH:15]([C:20]4[CH:24]=[CH:23][N:22](S(C5C=CC=CC=5)(=O)=O)[CH:21]=4)[CH2:14]3)[CH:11]=2)[C:6](=[O:35])[C:5]([C:36]([OH:38])=[O:37])=[CH:4]1)[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:34])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH:15]([C:20]4[CH:24]=[CH:23][NH:22][CH:21]=4)[CH2:14]3)[CH:11]=2)[C:6](=[O:35])[C:5]([C:36]([OH:38])=[O:37])=[CH:4]1)[CH3:2] | |f:1.2| | US04940710_ | 1,990 | C1COCCO1.O=S(=O)(c1ccccc1)[n:25]1[cH:24][cH:23][c:22]([CH:21]2[N:19]([CH3:20])[CH2:18][CH2:17][N:16]([c:15]3[c:13]([F:14])[cH:12][c:11]4[c:9](=[O:10])[c:5]([C:6](=[O:7])[OH:8])[cH:4][n:3]([CH2:2][CH3:1])[c:29]4[cH:28]3)[CH2:27]2)[cH:26]1.[Na+].[OH-]>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9](=[O:10])[c:11]2[cH:12][c:13]([F:14])[c:15]([N:16]3[CH2:17][CH2:18][N:19]([CH3:20])[CH:21]([c:22]4[cH:23][cH:24][nH:25][cH:26]4)[CH2:27]3)[cH:28][c:29]12 | 0.972594 | C1COCCO1.CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(C)C(c4ccn(S(=O)(=O)c5ccccc5)c4)C3)cc21.[Na+]~[OH-]>>CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(C)C(c4cc[nH]c4)C3)cc21 | C1COCCO1.CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(C)C(c4ccn(S(=O)(=O)c5ccccc5)c4)C3)cc21.[Na+].[OH-]>>CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(C)C(c4cc[nH]c4)C3)cc21 | US04940710_grants | f8cffcf39caf51c7c323d7fa3198e2e0b4bbb5b89eb77a4fec7e5a4e | C1COCCO1.O=S(=O)(c1ccccc1)[n:25]1[cH:24][cH:23][c:22]([CH:21]2[N:19]([CH3:20])[CH2:18][CH2:17][N:16]([c:15]3[c:13]([F:14])[cH:12][c:11]4[c:9](=[O:10])[c:5]([C:6](=[O:7])[OH:8])[cH:4][n:3]([CH2:2][CH3:1])[c:29]4[cH:28]3)[CH2:27]2)[cH:26]1.[Na+].[OH-] | [CH3:1][CH2:2][n:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9](=[O:10])[c:11]2[cH:12][c:13]([F:14])[c:15]([N:16]3[CH2:17][CH2:18][N:19]([CH3:20])[CH:21]([c:22]4[cH:23][cH:24][nH:25][cH:26]4)[CH2:27]3)[cH:28][c:29]12 | ([c:2]:[nH;D2;+0:1]:[c:3])>>(O=S(=O)(-[n;H0;D3;+0:1](:[c:2]):[c:3])-c1:c:c:c:c:c:1) | 47f9adbf065cf6735fe6fda83407f351027b34a5c91d02170fdcdf81 | 1 | 1 | C1COCCO1.[Na+].[OH-] | 771 |
438,726 | 1,898,528 | null | Br[C:2]1[CH:3]=[C:4]([C:16]#[N:17])[CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12]([NH2:14])=[O:13])=[C:7]2[CH3:15].[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[C:16]([C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:30])([F:29])[F:18])=[CH:21][CH:22]=3)[CH:3]=1)[N:9]([CH3:11])[C:8]([C:12]([NH2:14])=[O:13])=[C:7]2[CH3:15])#[N:17] | null | US20160185721A1_0196 | 2,016 | Br[c:10]1[c:9]2[n:7]([CH3:8])[c:3]([C:4]([NH2:5])=[O:6])[c:2]([CH3:1])[c:26]2[cH:25][c:22]([C:23]#[N:24])[cH:21]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1>>[CH3:1][c:2]1[c:3]([C:4]([NH2:5])=[O:6])[n:7]([CH3:8])[c:9]2[c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[cH:21][c:22]([C:23]#[N:24])[cH:25][c:26]12 | 0.288908 | Cc1c(C(N)=O)n(C)c2c(Br)cc(C#N)cc12.OB(O)c1ccc(C(F)(F)F)cc1>>Cc1c(C(N)=O)n(C)c2c(-c3ccc(C(F)(F)F)cc3)cc(C#N)cc12 | Cc1c(C(N)=O)n(C)c2c(Br)cc(C#N)cc12.OB(O)c1ccc(C(F)(F)F)cc1>>Cc1c(C(N)=O)n(C)c2c(-c3ccc(C(F)(F)F)cc3)cc(C#N)cc12 | US20160185721A1_0196apps | 44544e384c5295394b86b4231a4e99ad52ec736ab2cf9231b1607c36 | Br[c:10]1[c:9]2[n:7]([CH3:8])[c:3]([C:4]([NH2:5])=[O:6])[c:2]([CH3:1])[c:26]2[cH:25][c:22]([C:23]#[N:24])[cH:21]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1 | [CH3:1][c:2]1[c:3]([C:4]([NH2:5])=[O:6])[n:7]([CH3:8])[c:9]2[c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[cH:21][c:22]([C:23]#[N:24])[cH:25][c:26]12 | ([#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 |
318,837 | 1,036,085 | 1,755,976 | [I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13]([S:16][CH3:17])=[N:14][N:15]=3)[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13]([S:16][CH3:17])=[N:14][N:15]=3)[CH:9]=2)[N:4]([S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:3]=1 | |f:1.2| | US09321756B2_0634 | 2,016 | CN(C)C=O.Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][c:23]([CH3:24])[cH:25][cH:26]1.[CH3:1][S:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[c:13]([I:14])[cH:15][nH:16]3)[s:27]1.[H-].[Na+]>>[CH3:1][S:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[c:13]([I:14])[cH:15][n:16]3[S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][c:23]([CH3:24])[cH:25][cH:26]2)[s:27]1 | 0.453447 | CN(C)C=O.CSc1nnc(-c2ccc3[nH]cc(I)c3c2)s1.Cc1ccc(S(=O)(=O)Cl)cc1.[H-]~[Na+]>>CSc1nnc(-c2ccc3c(c2)c(I)cn3S(=O)(=O)c2ccc(C)cc2)s1 | CN(C)C=O.CSc1nnc(-c2ccc3[nH]cc(I)c3c2)s1.Cc1ccc(S(=O)(=O)Cl)cc1.[H-].[Na+]>>CSc1nnc(-c2ccc3c(c2)c(I)cn3S(=O)(=O)c2ccc(C)cc2)s1 | US09321756B2_0634grants | cec4293e7206ba791c7e5be48a00540e65100196040cbd24a6f33915 | CN(C)C=O.Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][c:23]([CH3:24])[cH:25][cH:26]1.[CH3:1][S:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[c:13]([I:14])[cH:15][nH:16]3)[s:27]1.[H-].[Na+] | [CH3:1][S:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[c:13]([I:14])[cH:15][n:16]3[S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][c:23]([CH3:24])[cH:25][cH:26]2)[s:27]1 | ([O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4])-[n;H0;D3;+0:6](:[c:5]):[c:7])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([c:5]:[nH;D2;+0:6]:[c:7]) | 76e5dcfc59d0995646419a7b5366f6a558a5c3ba2bb1ac4fcad7138b | 1 | 1 | CN(C)C=O.[H-].[Na+] | 648 |
295,271 | 961,588 | 1,617,700 | Br[C:2]1[C:18]([F:19])=[CH:17][C:5]2[O:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([C:14]([NH2:16])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1.[C:20]([C:22]1([OH:30])[CH2:27][CH2:26][CH2:25][N:24]([CH3:28])[C:23]1=[O:29])#[CH:21]>>[F:19][C:18]1[C:2]([C:21]#[C:20][C:22]2([OH:30])[CH2:27][CH2:26][CH2:25][N:24]([CH3:28])[C:23]2=[O:29])=[CH:3][C:4]2[C:10]3[N:11]=[C:12]([C:14]([NH2:16])=[O:15])[S:13][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:17]=1 | null | US09034866B2_0898 | 2,015 | Br[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[F:16])[O:17][CH2:18][CH2:19][c:20]1[s:21][c:22]([C:23]([NH2:24])=[O:25])[n:26][c:27]1-2.[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C:6]([OH:7])([C:8]#[CH:9])[C:28]1=[O:29]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C:6]([OH:7])([C:8]#[C:9][c:10]2[cH:11][c:12]3[c:13]([cH:14][c:15]2[F:16])[O:17][CH2:18][CH2:19][c:20]2[s:21][c:22]([C:23]([NH2:24])=[O:25])[n:26][c:27]2-3)[C:28]1=[O:29] | 0.988337 | C#CC1(O)CCCN(C)C1=O.NC(=O)c1nc2c(s1)CCOc1cc(F)c(Br)cc1-2>>CN1CCCC(O)(C#Cc2cc3c(cc2F)OCCc2sc(C(N)=O)nc2-3)C1=O | C#CC1(O)CCCN(C)C1=O.NC(=O)c1nc2c(s1)CCOc1cc(F)c(Br)cc1-2>>CN1CCCC(O)(C#Cc2cc3c(cc2F)OCCc2sc(C(N)=O)nc2-3)C1=O | US09034866B2_0898grants | 54e6fb5a1f6a4d2c328557129627029d975c2231ae2cc32545bfb0d3 | Br[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[F:16])[O:17][CH2:18][CH2:19][c:20]1[s:21][c:22]([C:23]([NH2:24])=[O:25])[n:26][c:27]1-2.[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C:6]([OH:7])([C:8]#[CH:9])[C:28]1=[O:29] | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C:6]([OH:7])([C:8]#[C:9][c:10]2[cH:11][c:12]3[c:13]([cH:14][c:15]2[F:16])[O:17][CH2:18][CH2:19][c:20]2[s:21][c:22]([C:23]([NH2:24])=[O:25])[n:26][c:27]2-3)[C:28]1=[O:29] | ([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 |
372,792 | 813,892 | null | [CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][N:7]([CH2:15][C:16]([O:18]CC1C=CC=CC=1)=[O:17])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:2]>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][N:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:15][C:16]([OH:18])=[O:17])[CH3:2] | null | US20090324581A1_1859 | 2,009 | CCO.[Pd].c1ccc(C[O:12][C:10]([CH2:9][N:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:11])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]([CH2:9][C:10](=[O:11])[OH:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | 0.442931 | CCO.CCOC(=O)CCN(CC(=O)OCc1ccccc1)C(=O)OC(C)(C)C.[Pd]>>CCOC(=O)CCN(CC(=O)O)C(=O)OC(C)(C)C | CCO.CCOC(=O)CCN(CC(=O)OCc1ccccc1)C(=O)OC(C)(C)C.[Pd]>>CCOC(=O)CCN(CC(=O)O)C(=O)OC(C)(C)C | US20090324581A1_1859apps | 5d6059ed482568b308e6ba5feb4921f322f40c0bbb0bfc8352f9caab | CCO.[Pd].c1ccc(C[O:12][C:10]([CH2:9][N:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:11])cc1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]([CH2:9][C:10](=[O:11])[OH:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | ([C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])>>([C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1) | 3358e9d74bcf91ba7e96568094da103c2e3a143a7d89e0937034db20 | 1 | 1 | CCO.[Pd] | 186 |
5,297 | 27,509 | 39,753 | [H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([CH:16]=[C:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:11]1)(=O)[CH3:8].[OH-].[Na+]>CCOCC>[CH2:7]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([CH:16]=[C:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:11]1)[CH3:8] | |f:0.1.2.3.4.5,7.8| | US04085210_ | 1,978 | CCOCC.O=[C:2]([CH3:1])[N:3]1[CH2:4][CH2:5][O:6][CH:7]([CH:8]=[C:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24]1.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][O:6][CH:7]([CH:8]=[C:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24]1 | 0.737966 | CC(=O)N1CCOC(C=C2c3ccccc3CCc3ccccc32)C1.CCOCC.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+].[Na+]~[OH-]>>CCN1CCOC(C=C2c3ccccc3CCc3ccccc32)C1 | CC(=O)N1CCOC(C=C2c3ccccc3CCc3ccccc32)C1.CCOCC.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-]>>CCN1CCOC(C=C2c3ccccc3CCc3ccccc32)C1 | US04085210_grants | df16768d13ae040c10b31a95bd3fde877e3c6d5beaa041809e31c710 | CCOCC.O=[C:2]([CH3:1])[N:3]1[CH2:4][CH2:5][O:6][CH:7]([CH:8]=[C:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24]1.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-] | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][O:6][CH:7]([CH:8]=[C:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24]1 | ([#7:2]-[CH2;D2;+0:1]-[C;D1;H3:3])>>(O=[C;H0;D3;+0:1](-[#7:2])-[C;D1;H3:3]) | 164bcd5926595fb14a6a9bdfa6263711f1e81657ce47f1a9ea439ccb | 1 | 1 | CCOCC.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-] | 112 |
175,944 | 613,533 | 1,017,632 | [Cl-].O[NH3+:3].[C:4](=[O:7])([O-])[OH:5].[Na+].CS(C)=O.[CH3:13][C:14]1[N:15]([C:39]2[CH:44]=[CH:43][C:42]([O:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[CH:41][CH:40]=2)[C:16](=[O:38])[C:17]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:26][CH:25]=2)=[C:18]([CH2:20][CH2:21][CH3:22])[N:19]=1>O.C(OCC)(=O)C>[CH3:13][C:14]1[N:15]([C:39]2[CH:40]=[CH:41][C:42]([O:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[CH:43][CH:44]=2)[C:16](=[O:38])[C:17]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[NH:3][C:4](=[O:7])[O:5][N:37]=3)=[CH:28][CH:29]=2)=[C:18]([CH2:20][CH2:21][CH3:22])[N:19]=1 | |f:0.1,2.3| | US07803940B2_3472 | 2,010 | CCOC(C)=O.CS(C)=O.O.[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[c:22](=[O:23])[c:24]1[CH2:25][c:26]1[cH:27][cH:28][c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2[C:36]#[N:41])[cH:42][cH:43]1.[Cl-].[NH3+:37][OH:38].[Na+].[O-][C:39](O)=[O:40]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[c:22](=[O:23])[c:24]1[CH2:25][c:26]1[cH:27][cH:28][c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2-[c:36]2[n:37][o:38][c:39](=[O:40])[nH:41]2)[cH:42][cH:43]1 | 0.564123 | CCCc1nc(C)n(-c2ccc(Oc3ccccc3)cc2)c(=O)c1Cc1ccc(-c2ccccc2C#N)cc1.CCOC(C)=O.CS(C)=O.O.O=C([O-])O~[Na+].[Cl-]~[NH3+]O>>CCCc1nc(C)n(-c2ccc(Oc3ccccc3)cc2)c(=O)c1Cc1ccc(-c2ccccc2-c2noc(=O)[nH]2)cc1 | CCCc1nc(C)n(-c2ccc(Oc3ccccc3)cc2)c(=O)c1Cc1ccc(-c2ccccc2C#N)cc1.CCOC(C)=O.CS(C)=O.O.O=C([O-])O.[Cl-].[NH3+]O.[Na+]>>CCCc1nc(C)n(-c2ccc(Oc3ccccc3)cc2)c(=O)c1Cc1ccc(-c2ccccc2-c2noc(=O)[nH]2)cc1 | US07803940B2_3472grants | 781080834aecfc11ec44c9d1fcd609be85e625532d6b1790917fd0df | CCOC(C)=O.CS(C)=O.O.[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[c:22](=[O:23])[c:24]1[CH2:25][c:26]1[cH:27][cH:28][c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2[C:36]#[N:41])[cH:42][cH:43]1.[Cl-].[NH3+:37][OH:38].[Na+].[O-][C:39](O)=[O:40] | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([CH3:7])[n:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[c:22](=[O:23])[c:24]1[CH2:25][c:26]1[cH:27][cH:28][c:29](-[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2-[c:36]2[n:37][o:38][c:39](=[O:40])[nH:41]2)[cH:42][cH:43]1 | ([O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]):[c:7]):[n;H0;D2;+0:8]:[o;H0;D2;+0:9]:1)>>(O-[C;H0;D3;+0:1](-[O-])=[O;D1;H0:2]).([N;H0;D1;+0:3]#[C;H0;D2;+0:4]-[c;H0;D3;+0:5](:[c:6]):[c:7]).([NH3+;D1:8]-[OH;D1;+0:9]) | 5ce62915ffd733d867ad1712c59c563f28cb61a6ab8defe277d8cb59 | 1 | 1 | CCOC(C)=O.CS(C)=O.O.[Cl-].[Na+] | 979 |
22,715 | 108,161 | 174,996 | [CH:1]([O:4][C:5]([NH:7][C:8]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[C:14]([CH3:26])[C:9]=1[C:10]([O:12]C)=[O:11])=[O:6])([CH3:3])[CH3:2]>[OH-].[Na+].COCCOC>[CH:1]([O:4][C:5]([NH:7][C:8]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:15]=[C:14]([CH3:26])[C:9]=1[C:10]([OH:12])=[O:11])=[O:6])([CH3:3])[CH3:2] | |f:1.2| | US04745116_ | 1,988 | COCCOC.C[O:25][C:23]([c:22]1[c:2]([CH3:1])[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]1[NH:15][C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])=[O:24].[Na+].[OH-]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]([NH:15][C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])[c:22]1[C:23](=[O:24])[OH:25] | 0.663105 | COC(=O)c1c(C)cc(OCc2ccccc2)cc1NC(=O)OC(C)C.COCCOC.[Na+]~[OH-]>>Cc1cc(OCc2ccccc2)cc(NC(=O)OC(C)C)c1C(=O)O | COC(=O)c1c(C)cc(OCc2ccccc2)cc1NC(=O)OC(C)C.COCCOC.[Na+].[OH-]>>Cc1cc(OCc2ccccc2)cc(NC(=O)OC(C)C)c1C(=O)O | US04745116_grants | 9f4c141bc63fe09fe7d4b28ba6d2d5c80888e8974cb6da03a2d17a59 | COCCOC.C[O:25][C:23]([c:22]1[c:2]([CH3:1])[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]1[NH:15][C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])=[O:24].[Na+].[OH-] | [CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]([NH:15][C:16](=[O:17])[O:18][CH:19]([CH3:20])[CH3:21])[c:22]1[C:23](=[O:24])[OH:25] | ([C:9]-[#8:8]-[c:7]1:[c:6]:[c:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:11]:[c:10]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[#8:8]-[C:9]):[c:10]:[c:11]:1) | 1f30ff7184a936c3d6949b8da68f661883b9aca9556111a18280f156 | 1 | 1 | COCCOC.[Na+].[OH-] | 222 |
311,855 | 1,013,568 | 1,715,358 | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1.O[CH2:26][CH:27]1[CH2:31][CH2:30][O:29][CH2:28]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([O:19][CH2:26][CH:27]3[CH2:31][CH2:30][O:29][CH2:28]3)=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1 | null | US09233946B2_0748 | 2,016 | O[C:13]([c:12]1[cH:11][cH:10][cH:9][c:8]([NH:7][S:4]([c:3]2[c:2]([CH3:1])[c:30]3[c:24]([s:23]2)[cH:25][cH:26][c:27]([Cl:28])[cH:29]3)(=[O:5])=[O:6])[cH:22]1)=[O:14].[OH:15][CH2:16][CH:17]1[CH2:18][CH2:19][O:20][CH2:21]1>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH2:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21]3)[cH:22]2)[s:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][c:30]12 | 0.356205 | Cc1c(S(=O)(=O)Nc2cccc(C(=O)O)c2)sc2ccc(Cl)cc12.OCC1CCOC1>>Cc1c(S(=O)(=O)Nc2cccc(C(=O)OCC3CCOC3)c2)sc2ccc(Cl)cc12 | Cc1c(S(=O)(=O)Nc2cccc(C(=O)O)c2)sc2ccc(Cl)cc12.OCC1CCOC1>>Cc1c(S(=O)(=O)Nc2cccc(C(=O)OCC3CCOC3)c2)sc2ccc(Cl)cc12 | US09233946B2_0748grants | eaeff1c2c9f6f7f5611542fa41a6539a4988309cb73d9877f58c572e | O[C:13]([c:12]1[cH:11][cH:10][cH:9][c:8]([NH:7][S:4]([c:3]2[c:2]([CH3:1])[c:30]3[c:24]([s:23]2)[cH:25][cH:26][c:27]([Cl:28])[cH:29]3)(=[O:5])=[O:6])[cH:22]1)=[O:14].[OH:15][CH2:16][CH:17]1[CH2:18][CH2:19][O:20][CH2:21]1 | [CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH2:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21]3)[cH:22]2)[s:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][c:30]12 | ([C:4]-[O;H0;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]-[OH;D1;+0:5]) | 462ff262701550e8361ae350b730fe337624136bbbc825e08432a1b4 | 1 | 1 | null | 33 |
22,153 | 105,614 | 170,734 | [C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:12]([O:23][CH3:24])[C:11]([CH3:25])=[C:10]2[C:6]=1[C:7](=[O:26])[O:8][CH2:9]2)(=[O:3])[NH2:2].C1(N=C=NC2CCCCC2)CCCCC1.O[CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>C1COCC1>[C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][C:19]([O:21][CH2:43][CH2:44][N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[O:20])=[C:12]([O:23][CH3:24])[C:11]([CH3:25])=[C:10]2[C:6]=1[C:7](=[O:26])[O:8][CH2:9]2)(=[O:3])[NH2:2] | null | US04727069_ | 1,988 | C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1.O[C:20]([CH2:19][CH2:18]/[C:16](=[CH:15]/[CH2:14][c:13]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[O:9][C:10]([NH2:11])=[O:12])[C:31](=[O:32])[O:33][CH2:34]2)[CH3:17])=[O:21].[OH:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][C:10]([NH2:11])=[O:12])[c:13]1[CH2:14]/[CH:15]=[C:16](\[CH3:17])[CH2:18][CH2:19][C:20](=[O:21])[O:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1)[C:31](=[O:32])[O:33][CH2:34]2 | 0.598862 | C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1.COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.OCCN1CCOCC1>>COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 | C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1.COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.OCCN1CCOCC1>>COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 | US04727069_grants | 467f5c75ed2de897f3b0fa8cf962877bd862f9b0b6d3cf3613859549 | C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1.O[C:20]([CH2:19][CH2:18]/[C:16](=[CH:15]/[CH2:14][c:13]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[O:9][C:10]([NH2:11])=[O:12])[C:31](=[O:32])[O:33][CH2:34]2)[CH3:17])=[O:21].[OH:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1 | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][C:10]([NH2:11])=[O:12])[c:13]1[CH2:14]/[CH:15]=[C:16](\[CH3:17])[CH2:18][CH2:19][C:20](=[O:21])[O:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1)[C:31](=[O:32])[O:33][CH2:34]2 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:5]-[C:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[OH;D1;+0:5]) | a6871142fd86a88cf89e8dce15586c0c2325bd32f2c5592778c4dcb1 | 1 | 1 | C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1 | 17 |
201,913 | 688,009 | 1,135,374 | [CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:2].[CH3:11][O:12][CH2:13][CH2:14]Br>C(O)C>[CH2:1]([N:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:14][CH2:13][O:12][CH3:11])[CH3:2] | null | US08067595B2_0254 | 2,011 | Br[CH2:4][CH2:5][O:6][CH3:7].CCO.[CH3:1][CH2:2][NH:3][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][O:6][CH3:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | 0.952392 | CCNCc1ccccc1.CCO.COCCBr>>CCN(CCOC)Cc1ccccc1 | CCNCc1ccccc1.CCO.COCCBr>>CCN(CCOC)Cc1ccccc1 | US08067595B2_0254grants | 77309fc86ab8d0ed73d35603692952c1ae8f15515f72efa3e1f4ae1a | Br[CH2:4][CH2:5][O:6][CH3:7].CCO.[CH3:1][CH2:2][NH:3][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | [CH3:1][CH2:2][N:3]([CH2:4][CH2:5][O:6][CH3:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]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])>>(Br-[CH2;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) | 8c9df7f4c910b7e7e5bda94f4a229eb328f6f7f5e6bd0c5fbb8cf97a | 0.5 | 2 | CCO | 722 |
153,932 | 548,220 | 917,288 | Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]([N:20]2[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21]2)=[O:19])[CH2:14][CH2:13]1.C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C>[F:9][C:8]([F:11])([F:10])[C:4]1[N:3]=[C:2]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]([N:20]3[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:21]3)=[O:19])[CH2:16][CH2:17]2)[CH:7]=[CH:6][CH:5]=1 | null | US07576089B2_0535 | 2,009 | CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[c:19]1[cH:20][cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[n:28]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH2:17][NH:18][CH2:29][CH2:30]2)[CH2:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH2:17][N:18]([c:19]3[cH:20][cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[n:28]3)[CH2:29][CH2:30]2)[CH2:31]1 | 0.125313 | CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)C2CCNCC2)C1.CCN(CC)CC.CCOC(C)=O.CN(C)C=O.FC(F)(F)c1cccc(Cl)n1>>CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)C2CCN(c3cccc(C(F)(F)F)n3)CC2)C1 | CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)C2CCNCC2)C1.CCN(CC)CC.CCOC(C)=O.CN(C)C=O.FC(F)(F)c1cccc(Cl)n1>>CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)C2CCN(c3cccc(C(F)(F)F)n3)CC2)C1 | US07576089B2_0535grants | dcced14ea1348e10fcc92d7b1816d8424486e6d550a9388e0ccb516e | CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[c:19]1[cH:20][cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[n:28]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH2:17][NH:18][CH2:29][CH2:30]2)[CH2:31]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH2:17][N:18]([c:19]3[cH:20][cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[n:28]3)[CH2:29][CH2:30]2)[CH2:31]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 | CCN(CC)CC.CCOC(C)=O.CN(C)C=O | 220 |
427,512 | 1,819,114 | null | [N:1]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=2)=[O:14])[N:10]=[N:9]1)=[N+:2]=[N-:3].[CH2:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:29]#[CH:30].O=C1O[C@H]([C@H](CO)O)C(O)=C1O>CC(O)(C)C.O>[C:34]([O:33][C:32](=[O:38])[NH:31][CH2:28][C:29]1[N:3]=[N:2][N:1]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:14])[NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=3)[N:10]=[N:9]2)[CH:30]=1)([CH3:37])([CH3:36])[CH3:35] | |f:3.4| | US20160009704A1_0276 | 2,016 | CC(C)(C)O.O.O=C1O[C@H]([C@@H](O)CO)C(O)=C1O.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]#[CH:11].[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][n:17]1[cH:18][c:19]([C:20](=[O:21])[NH:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][c:28]([O:29][C:30]([F:31])([F:32])[F:33])[cH:34]2)[n:35][n:36]1)=[N+:37]=[N-:38]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][n:12]([CH2:13][CH2:14][CH2:15][CH2:16][n:17]2[cH:18][c:19]([C:20](=[O:21])[NH:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][c:28]([O:29][C:30]([F:31])([F:32])[F:33])[cH:34]3)[n:35][n:36]2)[n:37][n:38]1 | 0.087647 | C#CCNC(=O)OC(C)(C)C.CC(C)(C)O~O.O=C1O[C@H]([C@@H](O)CO)C(O)=C1O.[N-]=[N+]=NCCCCn1cc(C(=O)NCc2cccc(OC(F)(F)F)c2)nn1>>CC(C)(C)OC(=O)NCc1cn(CCCCn2cc(C(=O)NCc3cccc(OC(F)(F)F)c3)nn2)nn1 | C#CCNC(=O)OC(C)(C)C.CC(C)(C)O.O.O=C1O[C@H]([C@@H](O)CO)C(O)=C1O.[N-]=[N+]=NCCCCn1cc(C(=O)NCc2cccc(OC(F)(F)F)c2)nn1>>CC(C)(C)OC(=O)NCc1cn(CCCCn2cc(C(=O)NCc3cccc(OC(F)(F)F)c3)nn2)nn1 | US20160009704A1_0276apps | 76e97a27e79b16616cf19c843f3c721ee18a28e3ca0267a0b7a3ce1e | CC(C)(C)O.O.O=C1O[C@H]([C@@H](O)CO)C(O)=C1O.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]#[CH:11].[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][n:17]1[cH:18][c:19]([C:20](=[O:21])[NH:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][c:28]([O:29][C:30]([F:31])([F:32])[F:33])[cH:34]2)[n:35][n:36]1)=[N+:37]=[N-:38] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][n:12]([CH2:13][CH2:14][CH2:15][CH2:16][n:17]2[cH:18][c:19]([C:20](=[O:21])[NH:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][c:28]([O:29][C:30]([F:31])([F:32])[F:33])[cH:34]3)[n:35][n:36]2)[n:37][n:38]1 | ([C:4]-[n;H0;D3;+0:5]1:[cH;D2;+0:3]:[c;H0;D3;+0:2](-[C:1]):[n;H0;D2;+0:7]:[n;H0;D2;+0:6]:1)>>([C:1]-[C;H0;D2;+0:2]#[CH;D1;+0:3]).([C:4]-[N;H0;D2;+0:5]=[N+;H0;D2:6]=[N-;H0;D1:7]) | b9149db9cbb6732a3e79e493ae892b906c459db26457fe2f945b56b7 | 0.5 | 2 | CC(C)(C)O.O.O=C1O[C@H]([C@@H](O)CO)C(O)=C1O | 963 |
224,100 | 751,756 | 1,238,832 | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1>CO.[Pt]>[NH2:20][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]1 | null | US08288413B2_0239 | 2,012 | CO.O=[N+:18]([O-])[c:17]1[c:11]([NH:10][CH:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:20][CH2:19]2)[cH:12][c:13]([Cl:14])[cH:15][cH:16]1.[Pt]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH2:18])[CH2:19][CH2:20]1 | 0.979293 | CCOC(=O)N1CCC(Nc2cc(Cl)ccc2[N+](=O)[O-])CC1.CO.[Pt]>>CCOC(=O)N1CCC(Nc2cc(Cl)ccc2N)CC1 | CCOC(=O)N1CCC(Nc2cc(Cl)ccc2[N+](=O)[O-])CC1.CO.[Pt]>>CCOC(=O)N1CCC(Nc2cc(Cl)ccc2N)CC1 | US08288413B2_0239grants | 002b77b34976e3ec175307bcc273a38751775f69ff44ff2a4dc09e28 | CO.O=[N+:18]([O-])[c:17]1[c:11]([NH:10][CH:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:20][CH2:19]2)[cH:12][c:13]([Cl:14])[cH:15][cH:16]1.[Pt] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH2:18])[CH2:19][CH2:20]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pt] | 1 |
209,434 | 708,632 | 1,167,419 | C[O:2][C:3](=O)[CH2:4][O:5][CH2:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[BH4-].[Na+]>CO>[S:8]1[CH:9]=[CH:10][N:11]=[C:7]1[CH2:6][O:5][CH2:4][CH2:3][OH:2] | |f:1.2| | US08138340B2_0210 | 2,012 | CO.CO[C:2](=[O:1])[CH2:3][O:4][CH2:5][c:6]1[n:7][cH:8][cH:9][s:10]1.[BH4-].[Na+]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][c:6]1[n:7][cH:8][cH:9][s:10]1 | 0.945779 | CO.COC(=O)COCc1nccs1.[BH4-]~[Na+]>>OCCOCc1nccs1 | CO.COC(=O)COCc1nccs1.[BH4-].[Na+]>>OCCOCc1nccs1 | US08138340B2_0210grants | 82139f4932e44a0a6ede5be9f0b826d315217770d8f0acccf42c627c | CO.CO[C:2](=[O:1])[CH2:3][O:4][CH2:5][c:6]1[n:7][cH:8][cH:9][s:10]1.[BH4-].[Na+] | [OH:1][CH2:2][CH2:3][O:4][CH2:5][c:6]1[n:7][cH:8][cH:9][s:10]1 | ([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 | CO.[BH4-].[Na+] | 343 |
380,988 | 945,463 | null | C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH2:22][N:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([C:32]4[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=4)=[C:24]3[C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(Cl)(Cl)Cl.CO.[Pd]>[C:38]([C:35]1[CH:34]=[CH:33][C:32]([C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:23]([CH2:22][C:17]3[CH:16]=[C:15]([C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=4)[CH:20]=[CH:19][C:18]=3[CH3:21])[C:24]=2[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:37][CH:36]=1)([CH3:41])([CH3:39])[CH3:40] | null | US20100240642A1_0262 | 2,010 | CO.ClC(Cl)Cl.[Pd].c1ccc(C[O:33][c:32]2[cH:31][cH:30][c:29](-[c:28]3[cH:27][c:26]([CH2:25][n:24]4[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:7](-[c:8]5[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]5)[c:18]5[cH:19][cH:20][cH:21][cH:22][c:23]54)[c:38]([CH3:39])[cH:37][cH:36]3)[cH:35][cH:34]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1[CH2:25][c:26]1[cH:27][c:28](-[c:29]2[cH:30][cH:31][c:32]([OH:33])[cH:34][cH:35]2)[cH:36][cH:37][c:38]1[CH3:39] | 0.381316 | CCOC(=O)c1c(-c2ccc(C(C)(C)C)cc2)c2ccccc2n1Cc1cc(-c2ccc(OCc3ccccc3)cc2)ccc1C.CO.ClC(Cl)Cl.[Pd]>>CCOC(=O)c1c(-c2ccc(C(C)(C)C)cc2)c2ccccc2n1Cc1cc(-c2ccc(O)cc2)ccc1C | CCOC(=O)c1c(-c2ccc(C(C)(C)C)cc2)c2ccccc2n1Cc1cc(-c2ccc(OCc3ccccc3)cc2)ccc1C.CO.ClC(Cl)Cl.[Pd]>>CCOC(=O)c1c(-c2ccc(C(C)(C)C)cc2)c2ccccc2n1Cc1cc(-c2ccc(O)cc2)ccc1C | US20100240642A1_0262apps | 55122af94cf65121f81aa2b5394b88935faf777ed5c6666d98a66c07 | CO.ClC(Cl)Cl.[Pd].c1ccc(C[O:33][c:32]2[cH:31][cH:30][c:29](-[c:28]3[cH:27][c:26]([CH2:25][n:24]4[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:7](-[c:8]5[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]5)[c:18]5[cH:19][cH:20][cH:21][cH:22][c:23]54)[c:38]([CH3:39])[cH:37][cH:36]3)[cH:35][cH:34]2)cc1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1[CH2:25][c:26]1[cH:27][c:28](-[c:29]2[cH:30][cH:31][c:32]([OH:33])[cH:34][cH:35]2)[cH:36][cH:37][c:38]1[CH3:39] | ([OH;D1;+0:2]-[c:1])>>([c:1]-[O;H0;D2;+0:2]-C-c1:c:c:c:c:c:1) | 5aae93a61569145ed18632d801932cdc99b7a496825e1c5156904263 | 1 | 1 | CO.ClC(Cl)Cl.[Pd] | 23 |
10,654 | 54,139 | 87,444 | [Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:15][CH2:14][CH2:13][O:6]1 | null | US04289903_ | 1,981 | Cc1ccc(S(=O)(=O)O)cc1.Cc1ccccc1.O.O[CH2:13][CH2:14][OH:15].[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)=[O:12]>>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[O:12][CH2:13][CH2:14][O:15]1 | 0.58802 | Cc1ccc(S(=O)(=O)O)cc1.Cc1ccccc1.O.O=C(CCCCl)c1ccccc1.OCCO>>ClCCCC1(c2ccccc2)OCCO1 | Cc1ccc(S(=O)(=O)O)cc1.Cc1ccccc1.O.O=C(CCCCl)c1ccccc1.OCCO>>ClCCCC1(c2ccccc2)OCCO1 | US04289903_grants | 5a86c45a513a9f7647b87b646fe462834f31a16d7898127f9760d542 | Cc1ccc(S(=O)(=O)O)cc1.Cc1ccccc1.O.O[CH2:13][CH2:14][OH:15].[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)=[O:12] | [Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[O:12][CH2:13][CH2:14][O:15]1 | ([C:4]-[C;H0;D4;+0:5]1(-[c:7])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1)>>(O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3]).([C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[c:7]) | cfb7af45b9228b0b4816b39ac88485ec7a9c16e516a184e5878be84a | 1 | 1 | Cc1ccc(S(=O)(=O)O)cc1.Cc1ccccc1.O | 93 |
367,640 | 725,734 | null | [CH2:1]([C@H:8]1[N:13]([C:14]([C:16]2[N:17]=[CH:18][N:19]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][C:28]3([CH2:34][NH:35][CH2:36][CH3:37])[OH:33])[C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:15])[CH2:12][CH2:11][N:10]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:45](OC(=O)C)(=O)[CH3:46].C(=O)(O)[O-:53].[Na+]>N1C=CC=CC=1>[C:36]([N:35]([CH2:34][C:28]1([OH:33])[CH2:29][CH2:30][CH2:31][CH2:32][CH:27]1[N:19]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:16]([C:14]([N:13]2[CH2:12][CH2:11][N:10]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[CH2:9][C@H:8]2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:15])[N:17]=[CH:18]1)[CH2:45][CH3:46])(=[O:53])[CH3:37] | |f:2.3| | US20090156612A1_2152 | 2,009 | CC(=O)O[C:45]([CH3:46])=[O:47].O=C([O-])O.[CH3:1][CH2:2][NH:3][CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[n:12]1[cH:13][n:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][CH2:20][N:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]2[CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[c:38]1-[c:39]1[cH:40][cH:41][cH:42][cH:43][cH:44]1.[Na+].c1ccncc1>>[CH3:1][CH2:2][N:3]([CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[n:12]1[cH:13][n:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][CH2:20][N:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]2[CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[c:38]1-[c:39]1[cH:40][cH:41][cH:42][cH:43][cH:44]1)[C:45]([CH3:46])=[O:47] | 0.187977 | CC(=O)OC(C)=O.CCNCC1(O)CCCCC1n1cnc(C(=O)N2CCN(C(=O)OC(C)(C)C)C[C@H]2Cc2ccccc2)c1-c1ccccc1.O=C([O-])O~[Na+].c1ccncc1>>CCN(CC1(O)CCCCC1n1cnc(C(=O)N2CCN(C(=O)OC(C)(C)C)C[C@H]2Cc2ccccc2)c1-c1ccccc1)C(C)=O | CC(=O)OC(C)=O.CCNCC1(O)CCCCC1n1cnc(C(=O)N2CCN(C(=O)OC(C)(C)C)C[C@H]2Cc2ccccc2)c1-c1ccccc1.O=C([O-])O.[Na+].c1ccncc1>>CCN(CC1(O)CCCCC1n1cnc(C(=O)N2CCN(C(=O)OC(C)(C)C)C[C@H]2Cc2ccccc2)c1-c1ccccc1)C(C)=O | US20090156612A1_2152apps | 3bfe4778ea458cfec7ff335ad4a63f79b91cc583fdc560b21c030747 | CC(=O)O[C:45]([CH3:46])=[O:47].O=C([O-])O.[CH3:1][CH2:2][NH:3][CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[n:12]1[cH:13][n:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][CH2:20][N:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]2[CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[c:38]1-[c:39]1[cH:40][cH:41][cH:42][cH:43][cH:44]1.[Na+].c1ccncc1 | [CH3:1][CH2:2][N:3]([CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[n:12]1[cH:13][n:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][CH2:20][N:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][C@H:30]2[CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[c:38]1-[c:39]1[cH:40][cH:41][cH:42][cH:43][cH:44]1)[C:45]([CH3:46])=[O:47] | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[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]-[NH;D2;+0:5]-[C:6]) | 850466ba28e440ccfbe243813dd37fe45c414b2a9ee742dafad2e7ee | 1 | 1 | O=C([O-])O.[Na+].c1ccncc1 | 369 |
190,514 | 655,865 | 1,083,717 | [F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:25]3[C:20](=[C:21]([OH:28])[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[CH:19]=[N:18]2)[CH:5]=[C:6]([F:16])[C:7]=1[O:8]CC1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:25]3[C:20](=[C:21]([OH:28])[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[CH:19]=[N:18]2)[CH:5]=[C:6]([F:16])[C:7]=1[OH:8] | null | US07960563B2_0316 | 2,011 | CCOC(C)=O.[Pd].c1ccc(C[O:16][c:15]2[c:13]([F:14])[cH:12][c:11](-[n:10]3[n:9][cH:8][c:7]4[c:5]([OH:6])[cH:4][c:3]([C:2]#[N:1])[cH:21][c:20]43)[cH:19][c:17]2[F:18])cc1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([OH:6])[c:7]2[cH:8][n:9][n:10](-[c:11]3[cH:12][c:13]([F:14])[c:15]([OH:16])[c:17]([F:18])[cH:19]3)[c:20]2[cH:21]1 | 0.906071 | CCOC(C)=O.N#Cc1cc(O)c2cnn(-c3cc(F)c(OCc4ccccc4)c(F)c3)c2c1.[Pd]>>N#Cc1cc(O)c2cnn(-c3cc(F)c(O)c(F)c3)c2c1 | CCOC(C)=O.N#Cc1cc(O)c2cnn(-c3cc(F)c(OCc4ccccc4)c(F)c3)c2c1.[Pd]>>N#Cc1cc(O)c2cnn(-c3cc(F)c(O)c(F)c3)c2c1 | US07960563B2_0316grants | 7f85fe3cded09e66cd269586daec105ba1abafbb4d3b2fa5383df642 | CCOC(C)=O.[Pd].c1ccc(C[O:16][c:15]2[c:13]([F:14])[cH:12][c:11](-[n:10]3[n:9][cH:8][c:7]4[c:5]([OH:6])[cH:4][c:3]([C:2]#[N:1])[cH:21][c:20]43)[cH:19][c:17]2[F:18])cc1 | [N:1]#[C:2][c:3]1[cH:4][c:5]([OH:6])[c:7]2[cH:8][n:9][n:10](-[c:11]3[cH:12][c:13]([F:14])[c:15]([OH:16])[c:17]([F:18])[cH:19]3)[c:20]2[cH:21]1 | ([#7;a:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]:[c:8]:1)>>([#7;a:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[O;H0;D2;+0:6]-C-c2:c:c:c:c:c:2):[c:7]:[c:8]:1) | 070f69f6b03715129049c62ab38dd740d79eaf5dea0769581c605df0 | 1 | 1 | CCOC(C)=O.[Pd] | 698 |
313,283 | 1,018,207 | 1,723,834 | Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:5]=2[N:6]=1.CC(C)([O-])C.[Na+].Cl.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][CH:32]2[CH2:37][CH2:36][CH:35]([O:38][CH2:39][C:40]([N:42]3[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)=[O:41])[CH2:34][CH2:33]2)=[CH:27][C:26]=1[C:48]([F:51])([F:50])[F:49])([O-:24])=[O:23]>C1(C)C=CC=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].C(Cl)(Cl)Cl.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>[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][CH:32]2[CH2:33][CH2:34][CH:35]([O:38][CH2:39][C:40]([N:42]3[CH2:47][CH2:46][N:45]([C:2]4[S:3][C:4]5[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:5]=5[N:6]=4)[CH2:44][CH2:43]3)=[O:41])[CH2:36][CH2:37]2)=[CH:27][C:26]=1[C:48]([F:51])([F:50])[F:49])([O-:24])=[O:23] | |f:1.2,3.4,6.7.8.9.10.11| | US09249102B2_0760 | 2,016 | Br[c:29]1[n:30][c:31]2[cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38][cH:39][c:40]2[s:41]1.CC(C)(C)[O-].Cc1ccccc1.Cl.ClC(Cl)Cl.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[O:1]=[C:2]([CH2:3][O:4][CH:5]1[CH2:6][CH2:7][CH:8]([NH:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]2)[CH2:23][CH2:24]1)[N:25]1[CH2:26][CH2:27][NH:28][CH2:42][CH2:43]1.[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>>[O:1]=[C:2]([CH2:3][O:4][CH:5]1[CH2:6][CH2:7][CH:8]([NH:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]2)[CH2:23][CH2:24]1)[N:25]1[CH2:26][CH2:27][N:28]([c:29]2[n:30][c:31]3[cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38][cH:39][c:40]3[s:41]2)[CH2:42][CH2:43]1 | 0.078925 | CC(C)(C)[O-]~[Na+].Cc1ccccc1.ClC(Cl)Cl~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].Cl~O=C(COC1CCC(Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)CC1)N1CCNCC1.FC(F)(F)c1ccc2sc(Br)nc2c1.c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>>O=C(COC1CCC(Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)CC1)N1CCN(c2nc3cc(C(F)(F)F)ccc3s2)CC1 | CC(C)(C)[O-].Cc1ccccc1.Cl.ClC(Cl)Cl.FC(F)(F)c1ccc2sc(Br)nc2c1.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=C(COC1CCC(Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)CC1)N1CCNCC1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>>O=C(COC1CCC(Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)CC1)N1CCN(c2nc3cc(C(F)(F)F)ccc3s2)CC1 | US09249102B2_0760grants | a4d3940700926c54300fec25f17994ad1942b6cbce47e008e29d9cf5 | Br[c:29]1[n:30][c:31]2[cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38][cH:39][c:40]2[s:41]1.CC(C)(C)[O-].Cc1ccccc1.Cl.ClC(Cl)Cl.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[O:1]=[C:2]([CH2:3][O:4][CH:5]1[CH2:6][CH2:7][CH:8]([NH:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]2)[CH2:23][CH2:24]1)[N:25]1[CH2:26][CH2:27][NH:28][CH2:42][CH2:43]1.[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1 | [O:1]=[C:2]([CH2:3][O:4][CH:5]1[CH2:6][CH2:7][CH:8]([NH:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]2)[CH2:23][CH2:24]1)[N:25]1[CH2:26][CH2:27][N:28]([c:29]2[n:30][c:31]3[cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38][cH:39][c:40]3[s:41]2)[CH2:42][CH2:43]1 | ([#16;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Br-[c;H0;D3;+0:1](:[#16;a:2]):[#7;a:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 53c334f21890a3a530f4d5497f5df8245897b0e169dadf5160559f17 | 1 | 1 | CC(C)(C)[O-].Cc1ccccc1.Cl.ClC(Cl)Cl.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1 | 657 |
176,268 | 614,200 | 1,018,541 | Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:32])[CH2:26][C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)[CH:21]=[CH:22][CH:23]=3)=[N:10][N:11]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[F:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37]>>[F:17][C:15]1[CH:14]=[CH:13][C:12]2[N:11]([N:10]=[C:9]([C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:32])[CH2:26][C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)[CH:21]=[CH:22][CH:23]=3)[C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:37][C:36]3[CH:38]=[CH:39][CH:40]=[C:34]([F:33])[CH:35]=3)[N:7]=2)[CH:16]=1 | null | US07807673B2_0567 | 2,010 | Cl[c:29]1[n:28][cH:27][cH:26][c:25](-[c:24]2[c:15](-[c:14]3[cH:13][cH:12][cH:11][c:10]([NH:9][C:2](=[O:1])[CH2:3][c:4]4[cH:5][cH:6][cH:7][s:8]4)[cH:39]3)[n:16][n:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]32)[n:38]1.[NH2:30][c:31]1[cH:32][cH:33][cH:34][c:35]([F:36])[cH:37]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][s:8]1)[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]3[c:24]2-[c:25]2[cH:26][cH:27][n:28][c:29]([NH:30][c:31]3[cH:32][cH:33][cH:34][c:35]([F:36])[cH:37]3)[n:38]2)[cH:39]1 | 0.988216 | Nc1cccc(F)c1.O=C(Cc1cccs1)Nc1cccc(-c2nn3cc(F)ccc3c2-c2ccnc(Cl)n2)c1>>O=C(Cc1cccs1)Nc1cccc(-c2nn3cc(F)ccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1 | Nc1cccc(F)c1.O=C(Cc1cccs1)Nc1cccc(-c2nn3cc(F)ccc3c2-c2ccnc(Cl)n2)c1>>O=C(Cc1cccs1)Nc1cccc(-c2nn3cc(F)ccc3c2-c2ccnc(Nc3cccc(F)c3)n2)c1 | US07807673B2_0567grants | 150dd65aaf53c677f61ff530f831ef20f98a2e0a865ed4a5a194d0a6 | Cl[c:29]1[n:28][cH:27][cH:26][c:25](-[c:24]2[c:15](-[c:14]3[cH:13][cH:12][cH:11][c:10]([NH:9][C:2](=[O:1])[CH2:3][c:4]4[cH:5][cH:6][cH:7][s:8]4)[cH:39]3)[n:16][n:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]32)[n:38]1.[NH2:30][c:31]1[cH:32][cH:33][cH:34][c:35]([F:36])[cH:37]1 | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][s:8]1)[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[n:16][n:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]3[c:24]2-[c:25]2[cH:26][cH:27][n:28][c:29]([NH:30][c:31]3[cH:32][cH:33][cH:34][c:35]([F:36])[cH:37]3)[n:38]2)[cH:39]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([NH2;D1;+0:4]-[c:5]) | c9384cff16d8f069182a19c69b5ea34c7f585d1701326a079e8522b5 | 1 | 1 | null | 808 |