Pyridine → HCID 67483081, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared as in Example 1, 300 mg, 0.91 mmol) in methylene chloride (10 mL) and N,N-dimethylformamide (1 drop) cooled to 0° C. was treated with a 2.0M solution of oxalyl chloride in methylene chloride (0.52 mL, 1.04 mmol). The reaction was stirred at 0° C. for 30 min. At this time, the reaction was concentrated in vacuo to give a light yellow oil. The residue was then treated with a solution of 2-amino-5-cyanopyridine (216 mg, 1.80 mmol) in tetrahydrofuran (5 mL) and pyridine (0.37 mL, 4.5 mmol). The reaction was then stirred at 25° C. for 16 h. At this time, the reaction was diluted with water (15 mL) and extracted with methylene chloride (3×25 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 7/3 hexanes/ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-cyano-pyridin-2-yl)-3-cyclopentyl-propionamide (53 mg, 86%) as a colorless oil: (ES)+-HRMS m/e calcd for C21H22ClN3O3S (M+H)+ 432.1143, found 432.1147.

Provenance & Evidence