Piperidine → HCID 178498733, compound

Participants

Reaction Conditions

Reaction Steps

To the suspension of 6-formyl-4-methoxy-quinoline-3-carboxylic acid methyl ester (example 1e, 100 mg, 0.4 mmol), 2-((1R,2S)-2-phenyl-cyclopropylamino)-thiazol-4-one (example 1f, 93 mg, 0.4 mmol) and benzolic acid (5 mg, 0.04 mmol) in toluene (2 mL) were added and piperidine (5 uL, 0.04 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, 70-230 mesh, 0%-10% methanol in methylene chloride in 30 min) afford 4-methoxy-6-[4-oxo-2-((1R,2S)-2-phenyl-cyclopropylamino)-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carboxylic acid methyl ester (55 mg, 30%) as a light yellow solid. LC-MS m/e 460 (MH+).

Provenance & Evidence