Lithium Hydroxide → 6-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid

HRID 410768Notes

Reaction equation

HRID 410768 reaction equation
C[O:2][C:3]([C:5]1[C:29]([F:30])=[CH:28][C:8]2[N:9]([CH3:27])[C:10]([NH:12][C:13]3[S:14][C:15]4[CH:21]=[C:20]([O:22][C:23]([F:26])([F:25])[F:24])[CH:19]=[CH:18][C:16]=4[N:17]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Li+]>>[F:30][C:29]1[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]2[N:11]=[C:10]([NH:12][C:13]3[S:14][C:15]4[CH:21]=[C:20]([O:22][C:23]([F:26])([F:25])[F:24])[CH:19]=[CH:18][C:16]=4[N:17]=3)[N:9]([CH3:27])[C:8]=2[CH:28]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 583976406-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 583977916-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acidYield 89.3%

Procedure

6-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (121 mg) was prepared by following General Procedure E starting from 6-fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester (140 mg) and lithium hydroxide (53 mg). LC/MS: m/z 427.8. 1H NMR (DMSO-d6, 400 MHz): δ 8.01 (d, 1H), 7.95 (s, 1H), 7.61 (d, 1H), 7.48 (d, 1H), 7.38 (d, 1H), 3.65 (s, 3H), —COOH and —NH proton signal was not observed.

Sources & evidence

ORD record
ord-aedbdf2c1f2a4e4f97c6dd613fffde7d
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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