Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate → methyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate

Participants

Reaction Steps

A glass Parr vessel was charged with 10% palladium on carbon catalyst (0.35 g, 0.1 eq. weight/weight (w/w)), methanol (50 mL) ethanol (50 ml) and Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate (3.5 g, 8.8 mmol). The vessel was evacuated and charged with hydrogen gas (45 psi, 3.1×105 Pa). The reaction was shaken at ambient temperature overnight (approximately 18 hours). The reaction mixture was filtered to remove the catalyst and concentrated to dryness. The crude product was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-30% CMA in chloroform) followed by recrystallization from acetonitrile to provide methyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate as a white solid.

Provenance & Evidence