Triethylamine → 3-{2-methoxy-4-[4-(3-thiomorpholin-4-yl-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-1,2,4-oxadiazol-5-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 50 mg of 3-{4-[4-(3-hydroxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one in 1.5 mL of dimethylformamide at 0° C. were added 0.015 mL of triethylamine and 0.008 mL of methanesulfonyl chloride. The resulting mixture was stirred at 0° C. for 30 minutes and then concentrated under reduced pressure, taken into dichloromethane, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was dissolved in 4 mL of dimethylformamide. To the resulting solution were added 0.012 mL of thiomorpholine, 0.017 mL of diisopropylethyl amine and 29 mg of potassium iodide. The reaction mixture was heated to 90° C. for 10 minutes under microwave irradiation in a sealed tube. It was then concentrated under reduced pressure, taken into dichloromethane, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient of methanol in dichloromethane), triturated in acetonitrile and filtered to give 5.3 mg of 3-{2-methoxy-4-[4-(3-thiomorpholin-4-yl-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-1,2,4-oxadiazol-5-one.

Provenance & Evidence