Hydrochloric Acid → 4-{3-Cyclohexyl-3-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-propyl}-benzoic acid

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Reaction Conditions

Reaction Steps

To a solution of 180 mg (0.327 mmol) 4-{3-cyclohexyl-3-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-propyl}-benzoic acid methyl ester in 3 ml dioxane was added 3 ml water and 41 mg (0.98 mmol) lithium hydroxide monohydrate. The reaction mixture was stirred for 4 h at 100° C. and then poured on 30 ml aqueous 1M hydrochloric acid and 30 ml ethyl acetate. The aqueous layer was extracted a second time with 30 ml ethyl acetate. The combined organic layers were washed with 30 ml brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by preparative HPLC (phenomenex gemini column) eluting with a gradient of acetonitril:water (50:50 to 95:5) to give the title compound as a light yellow solid (78%). MS (Turbo Spray): m/z=536.236 [M+H].

Provenance & Evidence