Benzenesulfonamide → HCID 69145341, compound

HRID 1593059Notes

Reaction equation

HRID 1593059 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.[C:36]1(S(N)(=O)=O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=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:33]=[CH:32][C:31]([NH:7][C:5]([NH:4][S:1]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)(=[O:3])=[O:2])=[O:6])=[CH:30][CH:29]=1)[CH:20]=[CH:19]2

Participants

4

Reactant 3

HCID 7370BenzenesulfonamideHCID 118190831-SulfonylureaHCID 58998471[2-(4-Amino-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 69145341HCID 69145341, 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 benzenesulfonamide to give N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-benzenesulfonamide. ES-MS (M+H)+=467.1; 1H-NMP (ΔMΣO-66) δ (ppm): 9.13-9.06 (bs, 1H), 7.98-7.92 (d, J=8.4 Hz, 2H), 7.70-7.56 (m, 4H), 7.44-7.37 (d, J=8.8 Hz, 2H), 7.39-7.24 (d, J=8.8 Hz, 2H), 7.21-7.18 (d, J=7.3 Hz, 1H), 6.74-6.66 (d, J=8.4 Hz, 1H), 6.56-6.48 (bs, 1H), 6.49-6.46 (d, J=7.7 Hz, 1H), 2.82-2.76 (bd, J=4.4 Hz, 3H).

Sources & evidence

ORD record
ord-f39ec48aef814c3eb233e734c27f5f84
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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