2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acid → HCID 45102806, compound

HRID 2265301Notes

Reaction equation

HRID 2265301 reaction equation
Cl.C[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]([Cl:39])[C:36]([Cl:40])=[CH:35][C:31]=3[C:32](O)=[O:33])(=[O:28])=[O:27])=[CH:23][CH:24]=[CH:25][C:18]=12>>[N:17]1[S:21][N:20]=[C:19]2[C:22]([S:26]([NH:29][C:30]3[CH:38]=[C:37]([Cl:39])[C:36]([Cl:40])=[CH:35][C:31]=3[C:32]([NH:6][C@@H:5]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[CH:9]=3)[C:4]([OH:3])=[O:16])=[O:33])(=[O:28])=[O:27])=[CH:23][CH:24]=[CH:25][C:18]=12

Participants

3

Reactant 2

HCID 160907562-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acidHCID 68768499(S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride

Product 1

HCID 45102806HCID 45102806, compound

Procedure

The title compound was prepared from 3-bromo-4-fluoro-L-phenylalanine methyl ester hydrochloride and 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoic acid as in Example 1, Part C, followed by hydrolysis of the resulting methyl ester as in EXAMPLE 2, Part E. HPLC: RT=10.10 min. MS (ESI−): mass calcd. for C22H14BrCl2FN4O5S2, 648.31; m/z found, 645/647/649 [M−H]−. 1H NMR (400 MHz, acetone-d6): 11.58 (s, 1H), 8.47-8.42 (m, 1H), 8.34-8.20 (m, 2H), 7.92-7.85 (m, 1H), 7.85-7.80 (m, 1H), 7.75-7.70 (m, 1H), 7.67-7.60 (m, 1H), 7.42-7.35 (m, 1H), 7.25-7.18 (m, 1H), 4.96-4.87 (m, 1H), 3.40-3.32 (m, 1H), 3.20-3.10 (m, 1H).

Sources & evidence

ORD record
ord-f787141b0f4a407f9041f93cc43346f7
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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