1-Hydroxybenzotriazole → HCID 66890455, compound

Participants

Reaction Steps

A solution of (S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid (51 mg, 0.21 mmol), HOBt (31 mg, 0.23 mmol) and HBTU (88 mg, 0.23 mmol) in DMF (5 mL) is stirred at room temperature for 30 min. Then a solution of —((S)-4-pyrrolidin-2-yl-pyridine-2-yl)-1H-benzoimidazole (10) in DMF (5 mL) is added, followed by diisopropylethylamine (135 mg, 1.05 mmol). After stirring at room temperature for 2 h, the reaction mixture is diluted with water and extracted with EtOAc. The combined organic layers are washed with water, sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by flash chromatography on silica gel (EtOAc/Hexane: 5%˜40%) to give {(S)-2-[(S)-2-(2-benzoimidazol-1-yl-pyridin-4-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester (71 mg, 67%) as a white solid. M/Z=504.2 [M+1]

Provenance & Evidence