1,1,1-Trimethoxybutane → HCID 86616898, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, pyridine hydrochloride (1.6 g, 14 mmol), trimethyl orthobutyrate (1.62 g, 11.0 mmol), 2-chloro-N4-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}quinoline-3,4-diamine (2.10 g, 5.49 mmol), and toluene (50 mL) were combined and heated at reflux for four hours under a Dean-Stark trap. The volatiles were removed under reduced pressure. The resulting oil was dissolved in ethyl acetate, and the solution was washed sequentially with aqueous potassium carbonate, water, and brine; dried over sodium sulfate; filtered; and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 4:6 hexane:ethyl acetate) to provide 1.22 g of 4-chloro-1-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-2-propyl-1H-imidazo[4,5-c]quinoline as a pale yellow solid.

Provenance & Evidence