O-Methylhydroxylamine hydrochloride → HCID 72448485, compound

Participants

Reaction Steps

Methoxylamine hydrochloride (0.57 g, 6.8 mmol) was added to a solution of 5-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridine-1-yl)pentan-2-one (1.31 g, 4.5 mmol) in methanol (30 mL) and stirred for 15 minutes. The reaction mixture was concentrated under reduced pressure, dissolved in dichloromethane (150 mL), washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate and concentrated under reduced pressure to afford 1.33 g of crude material. The crude material was purified by HPFC (silca gel, CMA 0-40% in chloroform) and dried overnight at 70° C. at 28 psi (1.9×105 Pa) to afford 0.75 g of 5-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridine-1-yl)pentan-2-one O-methyloxime as an off-white powder, mp 144.0-145.5° C. 1H NMR (300 MHz, DMSO-d6) δ 5.58 (s, 2H), 4.23 (t, J=8.1 Hz, 2H), 3.74 (s, H), 3.71 (s, H), 2.77 (t, J=7.5 Hz, 2H), 2.36 (s, 3H), 2.30 (s, 3H), 2.25 (t, J=7.5 Hz, 2H), 1.80 (m, J=7.5 Hz, 8H), 1.00 (t, J=6.9 Hz, 3H; MS (APCI) m/z 318 (M+H)+; Anal. calcd for C20H26N6O2: C, 64.32; H, 8.57; N, 22.06. Found: C, 64.19; H, 8.86; N, 22.32.

Provenance & Evidence