Hydrazine → HCID 11208418, compound

Participants

Reaction Steps

Anhydrous hydrazine (0.640 mL, 20.2 mmol) was added to a suspension of 2-[(4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl)methoxy]-1H-isoindole-1,3(2H)-dione (2.81 g, 6.75 mmol) in ethanol (40 mL). Gradually, a solution formed from which a solid began to precipitate. The reaction mixture was stirred overnight at room temperature, then was concentrated under reduced pressure. The residue was triturated with 1 M aqueous hydrochloric acid (50 mL). The mixture was sonicated and the solid was isolated by filtration. The filtrate was adjusted to pH 8 with solid sodium carbonate and extracted with dichloromethane (3×25 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford a yellow solid. The solid was triturated with methanol to afford 0.863 g of 2-[(aminooxy)methyl]-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a white solid.

Provenance & Evidence