Propylamine → HCID 86714116, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[(7-benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-butyric acid (30 mg, 0.074 mmol) and triethylamine (0.015 mL, 0.11 mmol) in CH2Cl2 (3 mL) was cooled in an ice bath. Isobutyl chloroformate (0.014 mL, 0.11 mmol) was added, and the mixture was stirred at 0° C. for 10 min. Propylamine (0.1 mL) was then added, and the mixture was slowly warmed to r.t. and stirred for 16 h. The mixture was diluted with CH2Cl2 (30 mL) and washed with 1 M HCl. The organic layer was dried over MgSO4 and concentrated. The crude product was purified twice by silica gel chromatography (0-30% EtOAc/CH2Cl2, then 10-80% EtOAc/hexanes+2% AcOH) to give 23 mg of the title compound as a white solid. MS: (+) m/z 448.35 (M+1).

Provenance & Evidence