Hydrochloric Acid → HCID 58967529, compound

Participants

Reaction Steps

1-[4-Amino-2-(ethoxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]-1,5-naphthyridin-7-yl]pyrrolidin-2-one (0.150 g, 0.39 mmol) from Example 13 was dissolved in dichloromethane (5 mL) and cooled with an ice bath. Boron tribromide (0.5 mL of a 1.0 M solution in dichloromethane) was added dropwise over 1 minute. The resulting slurry was stirred for 16 hours. The reaction mixture was acidified with 6 N hydrochloric acid (3 mL). The mixture was stirred until all of the solids dissolved. The biphasic mixture was made basic with 50% aqueous sodium hydroxide (˜6 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane, followed by extraction with a 10% methanol in dichloromethane solution. The organic fractions were combined and concentrated under vacuum. The residue was purified by HPFC eluting with a linear gradient of 2-30% CMA in chloroform. Recrystallization from acetonitrile afforded 1-[4-amino-2-(hydroxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-7-yl]pyrrolidin-2-one as 0.034 g of a white powder, m.p. 233-235° C.

Provenance & Evidence