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

HRID 1593050Notes

Reaction equation

HRID 1593050 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.[CH2:36]([C:39]1[S:43][C:42](S(N)(=O)=O)=[CH:41][CH:40]=1)[CH2:37][CH3:38]>>[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:33]=[CH:32][C:31]([NH:7][C:5]([NH:4][S:1]([C:42]3[S:43][C:39]([CH2:36][CH2:37][CH3:38])=[CH:40][CH:41]=3)(=[O:3])=[O:2])=[O:6])=[CH:30][CH:29]=1)[CH:20]=[CH:19]2

Participants

4

Reactant 3

HCID 118190831-SulfonylureaHCID 156693135-Propylthiophene-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 69144405N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-5-propylthiophene-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-propylthiophene-2-sulfonic acid amide to give N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-5-propylthiophene-2-sulfonamide. ES-MS (M+H)+=515.1; 1H-NMR (DMSO-d6) δ (ppm): 9.06-9.00 (s, 1H), 7.66-7.62 (d, J=12.4 Hz, 1H), 7.62-7.58 (d, J=3.7 Hz, 1H), 7.48-7.42 (m, 2H), 7.32-7.26 (m, 2H), 7.24-7.20 (d, J=7.3 Hz, 1H), 6.96-6-90 (d, J=3.6 Hz, 1H), 6.74-6.66 (d, J=8.4 Hz, 1H), 6.58-6.48 (bs, 1H), 6.50-6.46 (d, J=7.3 Hz, 1H), 2.84-2.76 (m, 5H), 1.68-1.56 (tq, J=7.3, 7.6 Hz, 2H), 0.94-0.86 (t, J=7.3 Hz, 3H).

Sources & evidence

ORD record
ord-c89e7a993c6f46fa8092d87732c9cc54
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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