Cesium carbonate → HCID 178477899, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of cesium carbonate (0.63 g, 1.94 mmol), 2-(azetidin-3-yl)-5-chloro-1H-benzo[d]imidazole dihydrochloride (as described in Preparation 5) (0.14 g, 0.49 mmol), and 2-chloro-3-(tetrahydro-2H-pyran-4-yloxy)pyrazine (0.10 g, 0.49 mmol) in DMA (1 mL) was heated to 100° C. for 16 h, then cooled to RT. The resulting suspension was partitioned between ethyl acetate and water, the layers were separated, and the organic layer was washed with water (2×), brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 5-chloro-2-(1-(3-(tetrahydro-2H-pyran-4-yloxy)pyrazin-2-yl)azetidin-3-yl)-1H-benzo[d]imidazole (0.16 g, 0.40 mmol, 83% yield) as a white solid. [M+1] 386. IC50 (uM) 0.9004.

Provenance & Evidence