Pyridine → HCID 10481771, 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, 200 mg, 0.606 mmol) in methylene chloride (5 mL) was treated with oxalyl chloride (116 μL, 1.212 mmol) and N,N-dimethylformamide (1 drop). The mixture was stirred at 25° C. for 1 h. The reaction mixture was concentrated in vacuo, and the residue was dried in vacuo. The residue was then dissolved in benzene, and the solvents were concentrated in vacuo. The residue was dried in vacuo. This material was dissolved in methylene chloride (5 mL), cooled to 0° C., and then treated with a mixture of 5-(5-amino-pyrazin-2-yl)-5-methyl-imidazolidine-2,4-dione (150 mg, 0.727 mmol) and pyridine (98 μL) in methylene chloride (1 mL) and dimethyl sulfoxide (1 mL). The ice bath was removed, and the solution was stirred at 25° C. overnight. The reaction mixture was concentrated in vacuo and then extracted with ethyl acetate and a 0.1N aqueous hydrochloric acid solution. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 1/4 hexanes/ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-methyl-2,5-dioxo-imidazolidin-4-yl)-pyrazin-2-yl]-propionamide (82 mg, 26%) as a light yellow solid: (ES)+-HRMS m/e calcd for C23H26ClN5O5S (M+H)+ 520.1416, found 520.1403.

Provenance & Evidence