Tetrahydrofuran → HCID 178425823, compound

Participants

Reaction Steps

To a solution of 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide (28 mg, 0.1 mmol, see Example 2A) in dry THF (5 ml) under nitrogen was added a 1 M solution of cyclohexylmagnesium bromide in THF (2M, 0.25 mL, 0.5 mmol) at room temperature. After the reaction of mixture was stirred at that temperature for 4 hours, 5 mL of water was added. The mixture was extracted with ethyl acetate (3×20 mL), washed with water and dried over MgSO4, and concentrated. The crude product was dissolved in 2 mL of methylene chloride. And then 1,1-carbonyldiimidazole (32 mg, 0.2 mmol) was added. After being stirred at room temperature for 1 hour, the mixture was diluted with 50 mL of ethyl acetate and water, and the ethyl acetate layer was separated, washed with water, brine and then dried over MgSO4. After filtration and concentration, the crude product was purified by preparatory HPLC to give a solid (22 mg, 57%). HPLC tR=1.94 min; MS m/z 392 [M+H]+.

Provenance & Evidence