Sodium hydride → HCID 178522110, compound

Participants

Reaction Steps

Sodium hydride (0.073 g, 1.8 mmol, 60% dispersion in mineral oil) was added to a stirred solution of trans-3-hydroxy-N-(pyridin-2-yl)cyclobutanecarboxamide (0.18 g, 0.92 mmol) in DMF (3.5 mL) under an argon atmosphere. The mixture was stirred at RT for 1 h. 2-fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine (0.17 g, 0.92 mmol) was added, and the reaction mixture was stirred at 60° C. for 18 h. The reaction mixture was diluted with EtOAc and washed with saturated ammonium chloride. The organic layer was separated, washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified via silica gel chromatography to give trans-N-(pyridin-2-yl)-3-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)cyclobutanecarboxamide as a white solid. [M+1]=354.0. IC50 (uM): 3.066.

Provenance & Evidence