O-Methylhydroxylamine hydrochloride → HCID 72448483, compound

Participants

Reaction Steps

Methoxylamine hydrochloride (0.59 g, 21 mmol, 1.5 eq) was added to a solution of 5-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one (1.54 g, 4.73 mmol, 1 eq) in methanol (20 mL) and stirred overnight. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (100 mL) and saturated aqueous sodium bicarbonate (75 mL). The aqueous layer was extracted with dichloromethane (2×25 mL) and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a yellow solid. The material was subjected to HPFC (silica gel, eluting with 0-25% CMA in chloroform), triturated with hot acetonitrile, filtered, and dried at 100° C. under vacuum for 24 hours to afford 1.66 g of 5-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one O-methyloxime as a white powder with an E/Z ratio of 80:20, mp 132-134° C. Anal. calcd for C19H26N6O: C, 64.38; H, 7.39; N, 23.71. Found: C, 64.19; H, 7.42; N, 23.76.

Provenance & Evidence