2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acid → HCID 11498491, compound

HRID 2265174Notes

Reaction equation

HRID 2265174 reaction equation
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:15]=3[C:16](O)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.Cl.C[O:26][C:27](=[O:38])[C@@H:28]([NH2:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Br:36])[CH:31]=1>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:15]=3[C:16]([NH:37][C@@H:28]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Br:36])[CH:31]=3)[C:27]([OH:26])=[O:38])=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 160906642-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acidHCID 68770773HCID 68770773, compound

Product 1

HCID 11498491HCID 11498491, compound

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acid was coupled to (S)-2-amino-3-(3-bromo-phenyl)-propionic acid methyl ester hydrochloride as in EXAMPLE 1, Part C. The methyl ester was hydrolyzed as in EXAMPLE 2, Part E, to afford the title compound. HPLC: RT=9.91 min. MS (ESI−): mass calcd. for C22H16BrIN4O5S2, 687.3; m/z found, 686 [M−H]−. 1H NMR (400 MHz, DMSO-d6): 13.05 (s, 1H), 11.77 (s, 1H), 9.03 (d, J=7.8, 1H), 8.45-8.35 (m, 2H), 7.92-7.86 (m, 1H), 7.82 (d, J=1.5, 1H), 7.53-7.51 (br m, 1H), 7.47-7.38 (m, 2H), 7.36-7.34 (m, 1H), 7.31-7.19 (m, 2H), 4.65-4.54 (m, 1H), 3.19 (dd, J=14.0, 4.7, 1H), 3.00 (dd, J=13.7, 10.8, 1H).

Sources & evidence

ORD record
ord-26d0192a10894c50a65897f58ec45797
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

Loading…