Triethylamine → HCID 16064896, compound

Participants

Reaction Steps

A solution of 3-[6-(2,4-difluorophenyl)-2-oxo-2H-quinolizin-1-yl]-4-fluorobenzoic acid (Example 31, 1.0 g, 2.53 mmol) in CH2Cl2 (20 mL) was added triethyl amine (511 mg, 5.06 mmol) and ethylchloroformate (409 mg, 3.79 mmol) at 0° C. The mixture was warmed to ambient temperature and allowed to stir for an additional 1 h. The reaction was quenched with aqueous NH4Cl, extracted with CH2Cl2 and washed with 0.5 N HCl (1×), brine, dried over MgSO4, and concentrated in vacou. The crude mixture was dissolved in CH2Cl2 and was added to a hydrazine solution (25.3 mmol of hydrazine in 10 mL CH2Cl2) via cannula. After stirring for 10 min at room temperature, the reaction was concentrated in vacuo to yield a solid. The crude solid was washed with MeOH and ether/EtOAc (1/1) to remove impurity. The resulting solid was added MeOH (5 mL) and trimethyl orthoacetate (20 mL) and heated to 110° C. for 2 hrs. LCMS revealed the reaction was complete and the mixture was concentrated in vacuo. The crude material was purified via silica gel chromatography (CH2Cl2/EtOAc/MeOH) to give the title compound as a yellowish solid (450 mg).

Provenance & Evidence