Methanol → HCID 51042061, compound

Participants

Reaction Steps

To a solution of 4-[2-[5-chloro-2-(1-cyclohexylmethyl-1H-benzoimidazol-2-yl)-phenyl]-ethyl]-benzonitrile (64 mg, 0.14 mmol; Example 74, intermediate a) in methanol (10 ml) was added a solution of potassium hydroxide (78 mg, 1.39 mmol) in water (5 ml) and the mixture was heated to reflux for 12 h. Solvents were removed under reduced pressure and the residue was diluted with water (10 ml) and acidified to pH 4 with 2M aqueous hydrochloric acid solution. It was then extracted three times with ethyl acetate (20 ml each), the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography over silica gel (65% ethyl acetate/n-hexane) to give the desired final product as a colorless powder (31%). MS (Turbo Spray): m/z=473.3 (M+H).

Provenance & Evidence