1-{4-amino-7-[2-(methylsulfonyl)ethenyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol → 1-{4-amino-7-[2-(methylsulfonyl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol

Participants

Reaction Conditions

Reaction Steps

A glass Parr vessel was charged with 10% palladium on carbon (0.1 g), methanol (50 mL) and 1-{4-amino-7-[2-(methylsulfonyl)ethenyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (380 mg, 1.05 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The reaction was shaken at 50° C. for approximately 18 hours. The reaction was cooled to ambient temperature, filtered, and then concentrated under reduced pressure. The resulting crude product was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-35% gradient of CMA in chloroform) followed by recrystallization from acetonitrile to provide 176 mg of 1-{4-amino-7-[2-(methylsulfonyl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as an off-white solid, mp 269-271° C.

Provenance & Evidence