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

Participants

Reaction Steps

O-benzylhydroxylamine hydrochloride (13.5 mg, 0.08 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 (23.0 mg, 0.06 mmol) in methanol (1.5 mL) at room temperature. The reaction mixture was stirred overnight. After concentration to dryness, the residue was purified by chromatography on silica gel using dichloromethane/methanol (9:1) as eluent. The title product was obtained as a pink solid (9 mg, 31%).

Provenance & Evidence