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

HRID 1593054Notes

Reaction equation

HRID 1593054 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.[Cl:36][C:37]1[CH:38]=[C:39](S(N)(=O)=O)[S:40][CH:41]=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:39]3[S:40][CH:41]=[C:37]([Cl:36])[CH:38]=3)(=[O:3])=[O:2])=[O:6])=[CH:32][CH:33]=1)[CH:20]=[CH:19]2

Participants

4

Reactant 3

HCID 118190831-SulfonylureaHCID 220194654-Chlorothiophene-2-sulfonamideHCID 58998471[2-(4-Amino-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 69146400N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-4-chlorothiophene-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 4-chlorothiophene-2-sulfonamide to give N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-4-chlorothiophene-2-sulfonamide. ES-MS (M+H)+=507.0, 509.0 (Cl).

Sources & evidence

ORD record
ord-184be4e898094bdda085a72641fbaaf4
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

Loading…