1-Sulfonylurea → HCID 69144758, compound

HRID 1593056Notes

Reaction equation

HRID 1593056 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[CH:39]=[C:40](S(N)(=O)=O)[S:41][CH:42]=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:40]3[S:41][CH:42]=[C:38]([CH:37]([F:47])[F:36])[CH:39]=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 69128921HCID 69128921, compound

Product 1

HCID 69144758HCID 69144758, compound

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-difluoromethylthiophene-2-sulfonamide to give N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-4-difluoromethylthiophene-2-sulfonamide. ES-MS (M+H)+=523.1; 1H-NMR (DMSO-d6) δ (ppm): 9.24-9.16 (bs, 1H), 8.34-8.28 (m, 1H), 7.88-7.84 (m, 1H), 7.66-7.60 (d, J=12.4 Hz, 1H), 7.48-7.42 (d, J=8.8 Hz, 2H), 7.34-7.26 (d, J=8.8 Hz, 2H), 7.25-7.20 (d, J=7.3 Hz, 1H), 7.19-6.91 (t, J=55.3 Hz, 1H), 6.72-6.66 (d, 8.4 Hz, 1H), 6.58-6.48 (bs, 1H), 6.50-6.46 (d, J=7.3 Hz, 1H), 2.82-2.77 (s, 3H).

Sources & evidence

ORD record
ord-2a5e2aba6a414802bcea014cd40b2719
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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