Dichloromethane → 6-{[({(3S,4S)-1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-hydroxy-3-pyrrolidinyl}methyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one Hydrochloride

Participants

Reaction Steps

1-{2-[(3S,4S)-3-(Aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one (108 mg; 0.353 mmol) and 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2003087098, Example 31(e)) (69 mg; 0.388 mmol) were combined in anhydrous DCM (5 ml) and anhydrous MeOH (1 ml) with a spatula of solid sodium carbonate. The reaction mixture was stirred under nitrogen for 18 h then sodium triacetoxyborohydride (235 mg; 1.06 mmol) was added and stirred for 1 h. The reaction mixture was concentraed and purified to obtain the free base of the title compound as a pale yellow oil (80 mg; 48%) after column chromatography (90:10:1: DCM:MeOH:NH4OH).

Provenance & Evidence