2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acid → HCID 58999902, compound

HRID 2265290Notes

Reaction equation

HRID 2265290 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:16])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[CH:9]=1)[NH2:6].[N:17]1[S:21][N:20]=[C:19]2[C:22]([S:26]([NH:29][C:30]3[CH:38]=[C:37]([Br:39])[CH:36]=[CH:35][C:31]=3[C:32](O)=[O:33])(=[O:28])=[O:27])=[CH:23][CH:24]=[CH:25][C:18]=12>>[CH3:2][O:3][C:4](=[O:16])[C@@H:5]([NH:6][C:32](=[O:33])[C:31]1[CH:35]=[CH:36][C:37]([Br:39])=[CH:38][C:30]=1[NH:29][S:26]([C:22]1[C:19]2=[N:20][S:21][N:17]=[C:18]2[CH:25]=[CH:24][CH:23]=1)(=[O:28])=[O:27])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[CH:9]=1

Participants

3

Reactant 2

HCID 160907442-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acidHCID 68768499(S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride

Product 1

HCID 58999902HCID 58999902, compound

Procedure

The title compound was prepared as in EXAMPLE 1, substituting 3-bromo-4-fluoro-L-phenylalanine methyl ester hydrochloride and 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-benzoic acid in Part C. HPLC: RT=10.39 min. MS (ESI−): mass calcd. for C23H17Br2FN4O5S2, 672.34; m/z found, 671 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.42 (s, 1H), 8.37 (d, J=7.1, 1H), 8.22 (d, J=8.8, 1H), 7.88 (s, 1H), 7.75-7.71 (m, 1H), 7.27-7.25 (m, 1H), 7.11 (q, J=8.4, 2H), 7.09-6.94 (m, 2H), 6.56 (d, J=7.0, 1H), 4.94 (q, J=5.8, 1H), 3.82 (s, 3H), 3.25-3.11 (m, 2H).

Sources & evidence

ORD record
ord-a0a470c5102e4df9a26c6e795e7f7aba
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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