4-Methylmorpholine → HCID 22466607, compound

Participants

Reaction Conditions

Reaction Steps

Dissolved 425 mg (5.06 mmol) 2-butynoic acid in 40 ml THF and chilled to 0° C. under N2. Added 556 μl (5.06 mmol) N-methylmorpholine and 658 μl (5.06 mmol) isobutyl chloroformate and stirred for 10 minutes. Added dropwise a solution of 1.00 g (3.37 mmol) 6-amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile in 2.0 ml hot 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 solids, and dried in vacuo, giving 735 mg of yellow solid: mass spectrum (electrospray m/e): M+H=363.3

Provenance & Evidence