Acetonitrile → HCID 58243473, compound

Participants

Reaction Steps

Methyl 2-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,3-oxazole-4-carboxylate (100 mg) and N-chlorosuccinimide (150 mg) were mixed with acetonitrile (4 ml), followed by heating to reflux for 48 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution and then saturated brine in this order, and dried over anhydrous magnesium sulfate. The resulting product was filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=2:1 to 1:10). The resulting residue was dissolved in ethyl acetate, 4M hydrogen chloride-ethyl acetate (1 ml) was added thereto and the solvent was evaporated under reduced pressure. The resulting solid was washed with ethyl acetate to obtain a white solid. The resulting solid was dissolved in methanol (3 ml) and a 1M aqueous sodium hydroxide solution (1 ml) was added thereto, followed by stirring for 30 minutes. Water and saturated brine were added to the reaction solution, followed by washing with ethyl acetate. 1M hydrochloric acid was added to the aqueous layer, followed by 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 solid was washed with ethyl acetate to obtain, as a white solid, 5-chloro-2-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,3-oxazole-4-carboxylic acid (8.2 mg).

Provenance & Evidence