Triethylamine → HCID 59320311, compound

Participants

Reaction Conditions

Reaction Steps

(6-Chloro-pyridazin-3-yl)-hydrazine (190 mg, 1.315 mmol) was dissolved in dimethylformamide followed by the addition of triethylamine (3 eq). This mixture was stirred for 5 minutes. The mixture became dark green and then was cooled 0° C. A solution of [3-(1-methyl-1H-pyrazol-4-yl)-quinolin-6-yl]acetyl chloride (375 mg, 1.315 mmol) in dimethylformamide was added dropwise and the reaction mixture turned dark yellow, and stirred for one hour. After such time mixture was concentrated to dryness then taken up in acetic acid (10 mL) and stirred at 60° C. for 16 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water, and the aqueous phase further extracted with ethyl acetate. The combined organics purified via flash column chromatography (SiO2, CH2Cl2, methanol gradient 0 to 10%) to return the title compound (217 mg, 42% yield). Analytical data presented in Table 2.

Provenance & Evidence