1-Sulfonylurea → N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-5-difluoromethylthiophene-2-sulfonamide

HRID 1593051Notes

Reaction equation

HRID 1593051 reaction equation
[S:1](=[N:4][C:5]([NH2:7])=[O:6])(=[O:3])=[O:2].C(OC(=O)[N:14]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[F:26])[C:22](=[O:27])[N:21]([C:28]1[CH:33]=[CH:32][C:31](N)=[CH:30][CH:29]=1)[CH:20]=[CH:19]2)C)(C)(C)C.[F:36][CH:37]([F:47])[C:38]1[S:42][C:41](S(N)(=O)=O)=[CH:40][CH:39]=1>>[NH2:14][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[F:26])[C:22](=[O:27])[N:21]([C:28]1[CH:29]=[CH:30][C:31]([NH:7][C:5]([NH:4][S:1]([C:41]3[S:42][C:38]([CH:37]([F:47])[F:36])=[CH:39][CH:40]=3)(=[O:3])=[O:2])=[O:6])=[CH:32][CH:33]=1)[CH:20]=[CH:19]2

Participants

4

Reactant 3

HCID 118190831-SulfonylureaHCID 58998471[2-(4-Amino-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl esterHCID 691276995-Difluoromethyl-thiophene-2-sulfonic acid amide

Product 1

HCID 69143569N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-5-difluoromethylthiophene-2-sulfonamide

Procedure

An analogous sulfonylurea coupling and de-protection procedure to that described in Example 29 was performed on [2-(4-Amino-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester (Example 9) and 5-difluoromethyl-thiophene-2-sulfonic acid amide to give N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-5-difluoromethylthiophene-2-sulfonamide. ES-MS (M+H)+=523.1; 1H-NMR (DMSO-d6) δ (ppm): 8.70-8.64 (s, 1H), 7.66-7.60 (d, J=12.4 Hz), 7.56-7.48 (m, 2h), 7.38-7.10 (t, J=55.3 Hz, 1H), 7.36-7.32 (m, 1H), 7.28-7.24 (m, 1H), 7.22-7.18 (d, J=7.7 Hz, 1H), 7.12-7.06 (m, 2H), 6.72-6.66 (d, J=8.4 Hz, 1H), 6.52-6.46 (bs, 1H), 6.48-6.44 (d, J=7.3 Hz, 1H), 2.81-2.77 (bd, J=4.7 Hz, 3H).

Sources & evidence

ORD record
ord-f4f1a79b128a41a88248023f3d011ee4
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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