Dimethylformamide → HCID 16065039, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[6-(2,4-difluorophenyl)-2-oxo-2H-quinolizin-1-yl]-3,5-difluorobenzoic acid (Example 38, 204 mg, 0.49 mmol) in CH2Cl2 (1.5 mL) was added oxalyl chloride (93 mg, 0.74 mmol) and a catalytic amount of DMF at 0° C. After stirring at 0° C. for 5 min, the reaction was warmed to room temperature and stirred an additional for 30 min. The reaction was concentrated in vacuo and azeotrophed with toluene (2×). The crude material was dissolved in CH2Cl2 (1.5 mL) and was added to a solution of hydrazine (50 mmol) in CH2Cl2 (2 mL) at 0° C. After stirring for 15 min, the reaction was complete via LCMS analysis and the reaction was condensed to a solid, and azeotrophed with toluene (2×). The crude material was dissolved in trimethyl orthoacetate (5 mL) and methanol (2 mL) and heated to 120° C. for 1.5 hours. All volatile material was removed under reduced pressure and the crude material was purified via silica gel chromatography (100% EtOAc).

Provenance & Evidence