Triethylamine → (1H-benzoimidazol-2-yl)-[3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-methanone

Participants

Reaction Steps

A mixture of 1H-benzoimidazole-2-carboxylic acid (19) (100 mg, 0.47 mmol), 2-azetidin-3-yl-3-chloro-pyrazine hydrochloride (8) (96 mg, 0.47 mmol), HATU (540 mg, 1.3 mmol) and Et3N (101 mg, 1 mmol) in dry DCM (10 mL) was stirred at RT overnight. Then the mixture reaction was poured into saturated aqueous Na2CO3 and extracted with DCM (50 mL×3), the organic layer was washed with brine, dried over Na2SO4 and concentrated to give the crude compound which was purified by ISCO silica gel column (10% to 80% EtOAc in petroleum ether) and followed by reverse phase prep. HPLC (10% to 80% water/MeCN) to afford pure (1H-benzoimidazol-2-yl)-[3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-methanone (84) (50 mg, 0.16 mmol, yield 34%).

Provenance & Evidence