Acetic Acid → N-Cyclobutyl-5-[2,6-dichloro-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-phenoxy]-2-hydroxy-N-methyl-benzamide

Participants

Reaction Steps

To a solution of the title compound of Step H (40 mg, 0.10 mmol) and thiazolidinedione (13 mg, 0.11 mmol) in toluene (2 ml) was added acetic acid (1.5 μl, 0.025 mmol), piperidine (2.5 μl, 0.025 mmol) and powdered 3 A° molecular sieves. The reaction mixture was heated to reflux and stirred at reflux for about 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (10 ml) and water (10 ml). The organic layer was washed with 1N HCl (2×10 ml), brine (10 ml), dried, filtered, and concentrated. The crude product was purified by preparative TLC (7% MeOH in dichloromethane) to afford the title compound (37 mg). MS (APCl−) Calc: 492.0, found: 491.0 (M−1).

Provenance & Evidence