Methylamine → HCID 58318616, compound

Participants

Reaction Steps

To a solution of 2-(1-(tert-butoxycarbonylamino)ethyl)-3-phenyl-1,5-naphthyridine-4-carboxylic acid (205 mg, 0.52 mmol) in DMF (5 mL) was added PyBop (407 mg, 1.5 mmol), methanamine (0.52 mL, 2.0 eq) and N-ethyl-N-isopropyl-propan-2-amine (0.18 mL, 2.0 eq). The resulting mixture was stirred at room temperature overnight. The mixture was partitioned between water (10 mL) and EtOAc (15 mL). The water layer was extracted with EtOAc (5 mL×2). The combined organics were washed with water (10 mL×2), 0.5 N NaOH (5 mL×2), water (5 mL×2), brine (5 mL) and dried over sodium sulfate. Removal of solvents followed with column chromatography on silica gel (EtOAc/hexane, up to 2/1) to give a white solid. Mass Spectrum (ESI) m/e=407 (M+1).

Provenance & Evidence