1,2-Dichloroethane → HCID 71543409, compound

Participants

Reaction Steps

A solution of 2-(2H-1,2,3-triazol-2-yl)benzoic acid (2.46 g, 13.0 mmol) (prepared as described in WO2008/147518, WO2009/143033 and WO2010/048012), 1-hydroxy-7-azabenzotriazole (1.77 g, 13.0 mmol), and EDC (2.95 g, 15.4 mmol) in DMF (20 mL) was stirred for 5 min. A solution of 2-{[(3R,6R)-6-methylpiperidin-3-yl]oxy}pyridine-4-carbonitrile hydrochloride (3.0 g, 11.8 mmol) in DMF (20 mL) and Hunig's Base (6.20 ml, 35.5 mmol) was added quickly dropwise via addition funnel. The reaction was stirred at RT overnight, then diluted with saturated, aqueous NaHCO3 and water and extracted with EtOAc. The organics were washed with brine, dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel gradient chromatography (0-75% ethyl acetate in hexanes), providing the titled compound as a white foam. HRMS m/z (M+H) 389.1714 found, 389.1721 required.

Provenance & Evidence