Methanol → HCID 58397397, compound

HRID 410893Notes

Reaction equation

HRID 410893 reaction equation
C[O:2][C:3]([C:5]1[CH:31]=[CH:30][C:8]2[N:9]([CH:27]([CH3:29])[CH3:28])[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+].CO>C1COCC1>[CH:27]([N:9]1[C:8]2[CH:30]=[CH:31][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=[C:10]1[NH:12][C:13]1[S:14][C:15]2[CH:21]=[C:20]([O:22][C:23]([F:24])([F:26])[F:25])[CH:19]=[CH:18][C:16]=2[N:17]=1)([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 58397547HCID 58397547, compound

Product 1

HCID 58397397HCID 58397397, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Isopropyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimid azole-5-carboxylic acid (500.0 mg) was prepared by following General Procedure E starting from 1-isopropyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester (580.0 mg) and lithium hydroxide (2.0 N solution, 3.0 mL), MeOH (2.0 mL) and THF (2.0 mL). LCMS: m/z 438; and 1H NMR (DMSO-d6, 400 MHz): δ 8.17 (1H, m), 7.96 (1H, m), 7.84-7.82 (1H, m), 7.72-7.70 (1H, m), 7.64-7.61 (1H, m), 7.40-7.37 (1H, m), 5.16-5.13 (1H, m), 1.59-1.58 (6H, d), —NH proton and —COOH signals were not observed.

Sources & evidence

ORD record
ord-1dadf96fef8a4d6daffabc6d89b64fcd
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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