Cesium carbonate → HCID 178477895, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-4-(tetrahydro-2H-pyran-4-yloxy)pyridine (0.060 g, 0.27 mmol), 2-(azetidin-3-yl)-5-chloro-1H-benzo[d]imidazole dihydrochloride (as described in Preparation 5) (0.076 g, 0.27 mmol), and cesium carbonate (0.35 g, 1.09 mmol) in NMP (0.5 mL) was heated to 130° C. for 24 h, then cooled to RT. Ethyl acetate and saturated aqueous ammonium chloride were added and the resulting biphasic mixture was separated. The organic layer was washed with water (2×), brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil that was purified by silica gel chromatography to give 5-chloro-2-(1-(4-(tetrahydro-2H-pyran-4-yloxy)pyridin-2-yl)azetidin-3-yl)-1H-benzo[d]imidazole (0.024 g, 0.062 mmol, 23% yield) as a light yellow solid. [M+1] 385. IC50 (uM) 1.087.

Provenance & Evidence