Benzoic Acid → 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-pyrazin-2-yl]-propionamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-formyl-pyrazin-2-yl)-propionamide (prepared as in Example 18, 44 mg, 0.1 mmol), 2,4-thiazolidinedione (18 mg, 0.15 mmol), piperidine (2 μL, 0.02 mmol), and benzoic acid (1.2 mg, 0.01 mmol) in anhydrous ethanol (5 mL) was heated under reflux overnight. The reaction mixture was allowed to cool to 25° C. and then was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 0%–60% ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-pyrazin-2-yl]-propionamide (40 mg, 75%) as a white solid: LC-MS m/e 535 (MH+).

Provenance & Evidence