Pyridine → HCID 22975843, compound

Participants

Reaction Conditions

Reaction Steps

A solution of [3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-urea (prepared in Example 1B-d, 402 mg, 1.22 mmol) and pyridine (0.15 mL, 1.83 mmol), in toluene (15 mL) was treated with ethyl malonyl chloride (0.19 mL, 1.5 mmol). The resulting reaction mixture was heated at reflux for 2 h. At this time, additional pyridine (0.15 mL, 1.83 mmol) and ethyl malonyl chloride (0.19 mL, 1.5 mmol) were added. The reaction was then heated at reflux for 90 min. The reaction was then cooled to 25° C., diluted with ethyl acetate (50 mL), washed with water (2×25 mL), and dried over magnesium sulfate. The solution was concentrated in vacuo. Flash column chromatography (Merck Silica gel 60, 230-400 mesh, 4/1 hexane/ethyl acetate) afforded 3-{3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-3-oxo-propionic acid ethyl ester (172 mg, 32%) as a colorless gum: EI-HRMS m/e calcd for C20H24Cl2N2O5 (M+) 443.1140, found 443.1128.

Provenance & Evidence