1,2-Dichloroethane → 5-(4-Fluorophenyl)-1-(3-hydroxy-3-methylbutan-2-yl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-6-oxo-1,6-dihydropyridine-3-carboxamide

Participants

Reaction Steps

To a solution of the sodium chloride salt of 5-(4-fluorophenyl)-1-(3-hydroxy-3-methylbutan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid (177 mg, 0.46 mmol) in N,N-dimethylformamide (2 mL) were added (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine hydrochloride salt (110 mg, 0.55 mmol), EDC (105 mg, 0.55 mmol), 1-hydroxy-7-azabenzotriazole (6 mg, 0.05 mmol) and N-methylmorpholine (0.121 mL, 1.10 mmol). The reaction mixture was stirred at ambient temperature. After 18 h, water was added. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→15% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound. HRMS 429.1973 (M+1).

Provenance & Evidence