Pyridine → HCID 90403384, compound

Participants

Reaction Steps

A mixture of Example B5 (0.568 g, 4.40 mmol) and oxalyl chloride (0.400 mL, 4.66 mmol) in DCE (10 mL) was heated at 100° C. for 1 h, cooled to RT, added to a solution of Example A9 (0.650 g, 2.93 mmol) and pyridine (0.400 mL, 4.96 mmol) in DCM (10 mL) and stirred at RT for 2 days. The mixture was treated with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN, sonicated, the solid collected via filtration and purified via silica gel chromatography (MeOH/DCM) to afford N-((5-((2-chloropyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (335 mg, 30%) as a white solid. MS (ESI) m/z: 377.1 (M+H+).

Provenance & Evidence