Pyridine → HCID 67482801, 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, 510 mg, 1.54 mmol) in methylene chloride (15 mL) and N,N-dimethylformamide (2 drops) was cooled to 5° C. and then treated with oxalyl chloride (0.27 mL, 3.09 mmol). After stirring for 5 min, the cooling bath was removed, and the stirring continued at 25° C. for 10 min. The solvents were concentrated in vacuo, the residue was dissolved in benzene (25 mL), and the solvent was concentrated in vacuo again. The resulting acid chloride was dissolved in methylene chloride (10 mL), cooled to 5° C. and then treated with a solution of 5-allyloxy-pyrazin-2-ylamine (238 mg, 1.57 mmol) and pyridine (0.32 mL, 3.96 mmol) in methylene chloride (15 mL). The mixture was further stirred at 25° C. for 16 h. The reaction mixture was then diluted with methylene chloride (25 mL) and washed with a saturated aqueous sodium bicarbonate solution (25 mL), a 0.5M aqueous hydrochloric acid solution (25 mL), and a saturated aqueous sodium chloride solution (25 mL). Each aqueous layer was back-extracted with another portion of methylene chloride (25 mL). The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, eluted with increasing concentrations of ethyl acetate/hexanes) afforded N-(5-allyloxy-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide as a white foam (574 mg, 80%).

Provenance & Evidence