Hydrochloric Acid → HCID 11673659, compound

Participants

Reaction Steps

A solution of boron tribromide in dichloromethane (11.8 mL of 1 M) was added to a chilled (0° C.) suspension of 1-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol hydrobromide (1.24 g, 3.93 mmol) in dichloromethane (30 mL). The reaction mixture was allowed to come to ambient temperature with stirring for 16 hours. Methanol (15 mL) and hydrochloric acid (10 mL of 6 N) were added and the reaction mixture was heated at reflux for 2.5 hours. The reaction mixture was made basic with sodium hydroxide and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined extracts were washed sequentially with water and brine, dried over magnesium sulfate, and then concentrated under reduced pressure to provide a white solid. This material was crystallized from ethyl acetate and then dried under vacuum at 95° C. for 16 hours to provide 0.55 g of 1-(4-amino-2-hydroxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol as a white powder, mp 235-237° C. Anal. calcd for C14H17N5O2: % C, 58.52; % H, 5.96; % N, 24.37. Found: % C, 58.40; % H, 5.82; % N, 24.45.

Provenance & Evidence