2-Aminothiazole → 3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide

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Reaction Steps

The title B compound, 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionic acid (3.44 mmol, 1.02 g) is suspended in thionyl chloride (5 mL) with a catalytic amount of DMF and stirred for 12 h. The mixture is evaporated and then diluted with toluene and re-evaporated to afford an oil which is diluted with 4 mL of DCM and added to 2-aminothiazole (3.8 mmol, 0.4 g) in 10 mL of pyridine at 0° C. and then stirred for 12 h while warming to RT. The reaction mixture is evaporated, diluted with EtOAc and 0.1 N HCl and the organic solution is washed with brine, dried and evaporated to an oil. Chromatography on silica (eluent: 5%→25% EtOAc in hexanes) affords 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide: 1H NMR δ 11.7 (s, 1H), 7.86 (d, J=8, 2H), 7.55 (d, J=3.5, 1H), 7.53 (d, J=8, 2H), 7.10 (d, J=3.5, 1H), 3.81 (t, J=7.5, 1H), 3.03 (s, 3H), 1.1-2.2 (m, 11H).

Provenance & Evidence