Hydrazine → HCID 16065040, compound

Participants

Reaction Steps

To a solution of 4-[6-(2,4-difluorophenyl)-2-oxo-2H-quinolizin-1-yl]-3,5-difluorobenzoic acid (Example 38, 50 mg, 0.12 mmol) in CH2Cl2 was added oxalyl chloride (22 mg, 0.18 mmol) and a catalytic amount of DMF at 0° C. After 10 min the reaction was removed from the ice bath and stirred at room temperature for 20 min. LCMS analysis revealed the reaction was complete and the reaction was concentrated in vacuo. To this crude reside in CH2Cl2 was added to a hydrazine solution (1.2 mmol hydrazine in 1 mL CH2Cl2) at 0° C. via cannula. After 10 min at 0° C. the reaction was allowed to warn to room temperature. The reaction was concentrated in vacuo to yield a solid which was added methanol (1 mL) and cyanogen bromide (126 mg, 1.2 mmol) and heated to 90° C. for 2 hrs. LCMS revealed the reaction was complete and the mixture was concentrated in vacuo. The crude material was purified via reverse phase chromatography to give the title compound (5.4 mg).

Provenance & Evidence