Acetic Acid → HCID 59130454, compound

Participants

Reaction Steps

A slurry of acetone O-{3-[4-amino-2-(ethoxymethyl)-7-phenyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}oxime (1.00 g, 2.31 mmol), 1 M sodium cyanoborohydride in tetrahydrofuran (4.62 mL, 4.62 mmol), methanol (12 mL), and acetic acid (4.5 mL) was stirred overnight at ambient temperature. The resulting solution was concentrated under reduced pressure and the residue was dissolved in chloroform (200 mL). The solution was washed with saturated aqueous sodium bicarbonate (2×40 mL) and brine (30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 1.0 g of 2-(ethoxymethyl)-1-{3-[(isopropylamino)oxy]propyl}-7-phenyl-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a yellow powder, mp 142.0-144.0° C.

Provenance & Evidence