Hydrochloric Acid → HCID 67024449, compound

Participants

Reaction Steps

CDI (144 mg) was added to a solution of 5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzoic acid (300 mg) in THF (3 ml), followed by stirring at room temperature for 1.5 hours. The reaction solution was added dropwise at 0° C. to a mixed solution of sodium borohydride in THF/water (6 ml, 1:1) under a nitrogen atmosphere, followed by stirring at room temperature for one hour. 1M hydrochloric acid was added to the reaction solution to cease the reaction and then neutralized with saturated aqueous sodium bicarbonate. After extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=95:5), the resulting solid (190 mg) was dissolved in ethyl acetate, and 4M hydrogen chloride-ethyl acetate was added thereto, followed by stirred for 30 minutes. The solution was concentrated under reduced pressure and powdered with diisopropylether to obtain [5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]methanol monohydrochloride (183 mg) as a white powder.

Provenance & Evidence