Water → HCID 11956299, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.747 g, 1.03 mL, 7.38 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.480 g, 4.92 mmol) were added to a stirring suspension of 2-chloromethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.750 g, 2.46 mmol) in DMF (5 mL). The resulting suspension was heated to 50° C. and stirred for 17 hours. The reaction mixture was cooled to room temperature and poured into water (100 mL). A solid was removed by filtration and discarded. The filtrate was extracted with ethyl acetate (3×100 mL). The combined organic fractions were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using a HORIZON HPFC system (silica cartridge, eluting with 5-20% methanol in dichloromethane). The resulting oil was crystallized from dichloromethane and isolated by filtration to yield 132 mg of 1-(2-Hydroxy-2-methylpropyl)-2-{[methoxy(methyl)amino]methyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 220-222° C.

Provenance & Evidence