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

HRID 1593053Notes

Reaction equation

HRID 1593053 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]([C:38]1[S:42][C:41](S(N)(=O)=O)=[CH:40][CH:39]=1)#[CH:37]>>[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]([C:36]#[CH:37])=[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 860437955-Ethynylthiophene-2-sulfonamide

Product 1

HCID 86598222N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-5-ethynylthiophene-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-ethynylthiophene-2-sulfonamide to give N-({[4-(6-amino-7-fluoro-1-oxoisoquinolin-2(1H)-yl)phenyl]amino}carbonyl)-5-ethynylthiophene-2-sulfonamide. ES-MS (M+H)+=497.1; 1H-NMR (DMSO-d6) δ (ppm): 9.22-9.18 (bs, 1H), 7.70-7.66 (m, 1H), 7.65-7.60 (d, J=12.4 Hz, 1H), 7.48-7.42 (d, J=9.1 Hz, 2H), 7.40-7.36 (m, 1H), 7.32-7.25 (d, J=8.8 Hz, 2H), 7.24-7.18 (d, J=7.7 Hz, 1H), 6.72-6.66 (d, J=8.4 Hz, 1H), 6.58-6.48 (bs, 1H), 6.50-6.46 (d, J=7.3 Hz, 1H), 4.86-4.84 (s, 1H), 2.82-2.76 (s, 3H).

Sources & evidence

ORD record
ord-9cc5343690c14570adb31c4512095acc
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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