Sodium Methoxide → HCID 10269444, compound

Participants

Reaction Steps

A dried round bottom flask was charged with a stir bar, 2,2,2-trichloro-N-{1-[2-(3-thien-2-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-yl}acetamide and sodium methoxide (25% in methanol, 11 mL, 49.8 mmol) at ambient temperature. The reaction was judged complete after 30 hours. The volatiles were removed under reduced pressure. The resulting oil was purified with chromatography over silica gel (95/5 dichloromethane/methanol), semi-preparative HPLC using method A, and recrystallization from ethyl acetate/hexane to provide 43 mg of 1-[2-(3-thien-2-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine as a white crystalline solid. m.p. 130.1-131.6° C.

Provenance & Evidence