Morpholine → 7-chloro-N-[4-(4-methylpiperazin-1-yl)-3-(morpholin-4-ylmethyl)phenyl]quinolin-4-amine

Participants

Reaction Steps

To {5-[(7-chloroquinolin-4-yl)amino]-2-(4-methylpiperazin-1-yl)phenyl}methanol (0.300 g, 0.78 mmol) in 6 mL of DMF at 0° C. was added thionyl chloride (0.28 mL, 5 eq). The reaction mixture was warmed up to room temperature and stirred for 2 h. The solvent was evaporated. The residue was suspended in 6 mL of DMF and morpholine (1.39 mL, 20 eq) was added at 0° C. The solution was stirred overnight at room temperature, evaporated and the residue was purified by flash chromatography (DCM/MeOH/NH4OH//9/1/0.1) to yield expected compound as a pale yellow solid (238 mg, 67% yield). m/z (ESI) 452.2 [M+H]+;

Provenance & Evidence