Sodium cyanoborohydride → HCID 86612257, compound

Participants

Reaction Steps

Sodium cyanoborohydride (2.26 g, 36.1 mmol) was added to a solution of 5-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one O-methyloxime (3.0 g, 7.22 mmol) in ethanol (50 mL) and acetic acid (3 mL) and stirred at ambient temperature overnight. Another portion of sodium cyanoborohydride was added (1.0 g) and the reaction was stirred for an additional 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was diluted in water and neutralized to pH ˜8 with 10% sodium hydroxide solution. The product was extracted into dichloromethane, washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated under reduced pressure to provide 2.73 g of N-[4-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-O-methylhydroxylamine.

Provenance & Evidence