Toluene → HCID 86592549, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of the {1-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-2-oxo-piperidin-4-yl}-acetic acid (190 mg, 0.422 mmol) in THF (5 mL) and methylene chloride (3 mL) is added triethylamine (0.09 ml, 0.633 mmol). The solution is cooled to 0° C., and 1M isopropyl chloroformate in toluene (0.422 mL, 0.422 mmol) is added. The homogenous mixture is allowed to warm to room temperature, and 4-chloro-1,2-phenylene-diamine (150 mg, 1.06 mmol) is added. The reaction is stirred at room temperature overnight. The volatile solvents are removed, and the resulting residue is chromatographed (SiO2, 5% MeOH/EtOAc) to give N-(2-amino-5-chloro-phenyl)-2-{1-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-2-oxo-piperidin-4-yl}-acetamide (200 mg, 82% yield). C34H30ClN5O2 MS m/z: 576, 578.

Provenance & Evidence