3-Methoxybenzylamine → HCID 57657272, compound

Participants

Reaction Steps

4-Amino-1-isobutyl-1H-imidazo[4,5-c]quinoline-8-carbaldehyde (237 mg, 0.66 mmol) and 3-methoxybenzylamine (100 mg, 1.3 mmol) were combined in methanol (25 mL) and dichloromethane (1 mL). The solution was purged with nitrogen gas and a 1M solution of sodium cyanoborohydride in THF (2 mL) was added. The reaction was stirred for 30 minutes. Additional sodium cyanoborohydride in THF (1M, 1 mL) was added and the reaction was stirred for an additional 15 minutes. Aqueous sodium carbonate (1%, 0.25 mL) was added and the reaction was stirred for 7 days. The solvent was removed under reduced pressure and approximately equal portions of chloroform and water were added. The fractions were separated and the organic fraction was sequentially dried (MgSO4), filtered, and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a CMA:chloroform gradient, 0-20% CMA). Recrystallization from acetonitrile provided 25 mg of 1-isobutyl-8-{[(3-methoxybenzyl)amino]methyl}-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, mp 125-126° C.

Provenance & Evidence