Hydrochloric Acid → HCID 178511323, compound

Participants

Reaction Steps

A solution of tert-butyl 2-(4-amino-2-ethoxy-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethylcarbamate (6 g, 16 mmol) in methanol (25 mL) was combined with a solution of hydrogen chloride in dioxane (102 mL of 4N). The reaction mixture was allowed to stir over night at ambient temperature and was then concentrated under reduced pressure to provide crude product as an orange solid. The solid was loaded onto a silica gel column. The column was eluted with 47.5% methanol/2.5% ammonium hydroxide in dichloromethane. The fractions were combined and concentrated under reduced pressure to provide an orange solid. The solid was triturated with hot acetonitrile and methanol and then allowed to cool. The solid was isolated by filtration and then washed sequentially with acetonitrile and diethyl ether to provide 3.5 g of 4-amino-1-(2-aminoethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-ol.

Provenance & Evidence