Piperidine → HCID 178466956, compound

Participants

Reaction Conditions

Reaction Steps

To the suspension of 4-ethoxy-6-formyl-quinoline-3-carbonitrile (example 14e) (68 mg, 0.3 mmol) and 2-((1R,2S)-2-phenyl-cyclopropylamino)-thiazol-4-one (example 1f, 70 mg, 0.3 mmol) in toluene (2 mL) was added benzolic acid (3.5 mg, 0.03 mmol) and piperidine (35 uL, 0.03 mmol). The mixture was heated to 150° C. by microwave for 20 min. After cooling to room temperature, the solid was collected by filtration, washed with toluene and dried. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-5% methanol in methylene chloride in 30 min) afforded 4-ethoxy-6-[4-oxo-2-((1R,2S)-2-phenyl-cyclopropylamino)-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (35 mg, 27%) as a light yellow solid: LC-MS m/e 441 (MH+).

Provenance & Evidence