Trifluoroacetic anhydride → HCID 58244070, compound

Participants

Reaction Steps

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 (375 mg) was mixed with dichloromethane (10 ml), and triethylamine (0.52 ml) was added, followed by ice-cooling and addition of trifluoromethanesulfonic anhydride (0.316 ml). After stirring at room temperature overnight, it was further stirred at 40° C. for 3 hours. DBU (0.222 ml) was added to the reaction solution, followed by stirring for one hour. Trifluoroacetic anhydride was added to the reaction solution, followed by stirring at 40° C. for 3 hours, and trifluoroacetic anhydride (0.158 ml) and triethylamine (0.52 ml) were added thereto, followed by stirring at 40° C. for one hour. The reaction solution was cooled to room temperature and saturated aqueous sodium bicarbonate was added thereto, followed by extraction with chloroform. The organic layer was washed with water and then saturated brine in this order, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=200:1), and the resulting residue was washed with diisopropylether to obtain, as a beige solid, 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-carbonitrile (190 mg).

Provenance & Evidence