2-Benzimidazolecarboxylic acid → HCID 54674275, compound

To a mixture of 1H-benzoimidazole-2-carboxylic acid (124 mg, 0.76 mmol) in DMF (5 mL) was added TEA (152 mg, 1.5 mmol) and HATU (347 mg, 0.92 mmol). The reaction mixture was stirred for 5 min and 2-azetidin-3-yl-3-phenyl-pyridine hydrochloride (100 mg, 0.76 mmol) was added. The reaction mixture was stirred at RT overnight. The mixture was diluted with water (10 mL), and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (5 mL) and brine (5 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by column chromatography to give (1H-benzoimidazol-2-yl)-[3-(3-phenyl-pyridin-2-yl)-azetidin-1-yl]-methanone (100 mg, 0.28 mmol, 59% yield) as a light yellow solid.

1. stirringThe reaction mixture was stirred at RT overnight
2. extractionextracted with EtOAc (2×20 mL)
3. washThe combined organic extracts were washed with water (5 mL) and brine (5 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customThe filtrate was evaporated in vacuo
7. customthe residue was purified by column chromatography

ORD record

ord-56161959b638477eaa14879450c63537

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957073B2