Hydrochloric Acid → HCID 57557270, compound

Participants

Reaction Steps

A solution of 2-[2-(benzyloxy)ethyl]-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (0.78 g, 1.98 mmol) dissolved in 20 mL of methanol was treated with 10% palladium on carbon (200 mg) and 0.68 mL of 3 M HCl in ethanol. The mixture was shaken under H2 at 50 PSI (3.4×105 Pa) overnight. Additional 10% palladium on carbon (200 mg) and 3 M HCl in ethanol (0.33 mL) were added and shaking was continued for 24 hours. The reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with methanol and the combined filtrates were concentrated under reduced pressure. The resulting material was treated with 20 mL of H2O and 2 mL of concentrated NH4OH solution and extracted into CHCl3 (3×25 mL). The combined organic layers were concentrated under reduced pressure. Chromatography (SiO2, 15-30% CMA/CHCl3) gave a white powder. Crystallization from ethanol/H2O gave 276 mg of 2-[4-amino-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]ethanol as white needles, mp 224-225° C.

Provenance & Evidence