Triethylamine → N-{4-[(3-Chloro-4-thiophenoxyphenyl)amino]-3-cyano-6-quinolinyl}-2-propenamide

Participants

Reaction Conditions

Reaction Steps

Dissolved 1.00 g (2.48 mmol) 6-amino-4-[(3-chloro-4-thiophenoxyphenyl)amino]-3-quinolinecarbonitrile in 2.0 ml DMF and 12 ml THF and chilled to 0° C under N2. Added 380 μl (2.73 mmol) triethylamine and 227 μl (2.73 mmol) acryloyl chloride. Removed ice bath at 15 minutes and at 1.5 hours stripped solvent and slurried residue with dilute sodium bicarbonate. Collected solids and washed with water. Recrystallized from ethyl acetate and dried in vacuo, giving 293 mg of yellow-orange solid: mass spectrum (electrospray m/e): M+H=457.3. 459.3.

Provenance & Evidence