Sodium Hydroxide → HCID 86612255, compound

Participants

Reaction Steps

Methoxylamine hydrochloride (0.25 g, 3.0 mmol) in water (4 mL) was added to a solution of 5-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one (0.81 g, 2.5 mmol) in ethanol (25 mL) and stirred at ambient temperature for 3 hours. Addition of acetic acid (20 mL) and sodium cyanoborohydride (2.0 g, 32 mmol) to the reaction mixture followed. After 2.5 hours, the reaction mixture was cooled to 0° C. and the pH was adjusted to ˜8 with 25% sodium hydroxide solution. The mixture was concentrated under reduced pressure, diluted with dichloromethane (75 mL) and saturated aqueous sodium bicarbonate and the layers were separated. The combined organic layers were washed with water (25 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 0.64 g of N-[4-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-O-ethylhydroxylamine.

Provenance & Evidence