Dimethyl Sulfoxide → 1-(1-(6-(4-Methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-2-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

0.080 ml of oxalyl chloride and 0.087 ml of dimethylsulfoxide were added in order to 3 ml of methylene chloride at −78° C., and the reaction liquid was stirred at −78° C. for 10 minutes, and then a methylene chloride (2 ml) solution of 146 mg of the diastereomer mixture of 1-(1-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-2-yl)-ethanol obtained in Examples 354 and 355, at −78° C. The reaction liquid was stirred at −78° C. for 30 minutes, and 0.42 ml of triethylamine was added to it, and the reaction mixture was stirred at −78° C. for 10 minutes, and then heated up to room temperature. Aqueous saturated ammonium chloride was added to the reaction liquid, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a pale yellow solid.

Provenance & Evidence