O-Methylhydroxylamine hydrochloride → HCID 86612268, compound

Participants

Reaction Steps

Methoxylamine hydrochloride (2.23 g, 26.7 mmol) was added to a solution of 5-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one (6.06 g of crude material prepared as described in Parts A and B of Example 22) in methanol (80 mL). The reaction mixture was stirred at room temperature for 48 hours and then concentrated under reduced pressure. The residue was dissolved dichloromethane (60 mL) and the pH was adjusted to 8 by the addition of saturated aqueous sodium bicarbonate (40 mL) and then solid sodium bicarbonate. The layers were separated and the aqueous layer was extracted with dichloromethane (30 mL). The combined organics were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to afford 6.33 g of 5-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one O-methyloxime a yellow oil.

Provenance & Evidence