Dimethylamine → N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}-3,6-bis(dimethylamino)hexanamide

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}6-chloro-2-hexenamide (0.58 g, 1.0 mmol), NaI (0.15 g, 1.0 mmol), tetrabutylammonium iodide (74 mg, 0.20 mmol), 4.0 ml of dimethylformamide, and 10 ml of 2.0 M dimethylamine in tetrahydrofuran was heated at 50° C. for 8 h. After the addition of 5 ml more 2.0 M dimethylamine in tetrahydrofuran the mixture was heated at 50° C. for an additional 8 h. After evaporation of the dimethylamine and tetrahydrofuran, the mixture was stirred in water, brought to pH˜9 with potassium carbonate, and filtered. The crude product was washed with water, dried, and chromatographed on silica gel with methylene chloride-ethyl acetate-methanol-triethylamine to give 464 mg of the title compound as an off-white solid; mass spectrum (electrospray, m/e) 628.9 (M+H)+, 315.1 (M+2H)+2.

Provenance & Evidence