1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine → 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N,N-bis(4-methoxybenzyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (2.0 g, 3.5 mmol) in trifluoroacetic acid (20 mL) was stirred at room temperature for 16 hours. The trifluoroacetic acid was removed under reduced pressure, and the residue was triturated with aqueous hydrochloric acid (25 mL of 6 N) and ethanol (20 mL) for 30 minutes. The resulting mixture was adjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide and stirred at 0° C. for 30 minutes. A solid was present and was isolated by filtration and purified by column chromatography on silica gel (eluting with 5% to 10% CMA in chloroform). The resulting solid was dried under high vacuum at 100° C. for 18 hours to provide 0.708 g of 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 244.0-246.0° C.

Provenance & Evidence