O-propylhydroxylamine hydrochloride → 1'-methyl-6-[(E)-3-[3-[(E)-C-methyl-N-propoxycarbonimidoyl]azetidin-1-yl]-3-oxoprop-1-enyl]spiro[1,4-dihydro-1,8-naphthyridine-3,4'-piperidine]-2-one

Participants

Reaction Steps

1-(Aminooxy)propane hydrochloride (10.5 mg, 0.093 mmol) was added to a solution of (E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-1′-methyl-1H-spiro[[1,8]naphthyridine-3,4′-piperidin]-2(4H)-one (20.0 mg, 0.052 mmol) in methanol/dichloromethane (1.5 mL, 9:1) at room temperature. The reaction mixture was stirred overnight. After concentration to dryness, the residue was purified by chromatography on silica gel using chloroforme/methanol (9:1) as eluent. Triturations in acetone allowed isolation of the title product as a white solid (9 mg, 39%).

Provenance & Evidence