4-Methylmorpholine → N-{4-[(3-Chlorophenyl)amino]-3-cyano-6-quinolinyl]-2-butynamide

Participants

Reaction Conditions

Reaction Steps

Dissolved 428 mg (5.09 mmol) 2-butynoic acid in 40 ml THF and chilled to 0° C. under N2. Added 560 μl (5.09 mmol) N-methylmorpholine and 662 μl (5.09 mmol) isobutyl chloroformate and stirred for 10 minutes. Added dropwise a solution of 1.00 g (3.39 mmol) 6-amino-4-[(3-chlorophenyl)amino]-3-quinolinecarbonitrile in 2 ml DMF and 20 ml THF. Removed ice bath at 15 minutes and stirred at 25° C. overnight. Stripped solvent, slurried residue with water and collected solids. Boiled in ethyl acetate, collected and dried in vacuo, giving 975 mg of yellow solid: mass spectrum (electrospray m/e): M+H=361.1, 363.2.

Provenance & Evidence