Dimethylformamide → HCID 25123070, compound

Participants

Reaction Steps

2-Piperidin-1-ylethanol (43 mg, 0.34 mmol) was treated with a 60% dispersion of NaH in mineral oil (17 mg, 0.42 mmol) in 2 mL of DMF. The mixture was stirred for 20 minutes and the 1,6-naphthyridine chloride was added, and the solution was stirred at 50° C. for 16 hours. The solution was cooled to room temperature and diluted with EtOAc and H2O. The organic layer was separated and washed with saturated aqueous sodium bicarbonate solution (NaHCO3) and brine, and dried over magnesium sulfate. The organics were filtered, concentrated, and purified by silica gel chromatography eluting with a gradient of dichloromethane/MeOH/NH4OH to yield 33 mg (41%) of compound 16. LCMS (EI) m/z 274 (M+1).

Provenance & Evidence