Morpholine → HCID 178512318, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (30 mg, 0.105 mmol) and N,N-diisopropylethylamine (40.9 mg, 55.2 μL, 0.316 mmol) in NMP (0.5 mL) was added diphenyl-cyanocarbonimidate (25.1 mg, 0.105 mmol). After 1 hr., morpholine (11.9 mg, 12.0 μL, 0.137 mmol) was added and the mixture was warmed to 120° C. in a sealed microwave tube. After 1 hr., LCMS showed complete conversion to product. The mixture was allowed to cool to room temp. and the crude product was purified using preparative reverse-phase HPLC. The product [(7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amino]-morpholin-4-yl-methylene-cyan-amide (25 mg, 56%) was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.26 (d, J=8.8 Hz, 1H) 8.07 (s, 1H) 7.61-7.76 (m, 3H) 7.57-7.62 (m, 2H) 7.48-7.53 (m, 1H) 7.46 (dd, J=8.8, 1.9 Hz, 1H) 6.93 (d, J=1.9 Hz, 1H) 4.36 (d, J=4.8 Hz, 2H) 3.51-3.62 (m, 4H) 3.35-3.46 (m, 4H).

Provenance & Evidence