Diisopropylethylamine → HCID 178466950, compound

Participants

Reaction Conditions

Reaction Steps

The suspension of 4-ethoxy-6-[2-methylsulfanyl-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (example 14 g) (71 mg, 0.2 mmol), m-fluorophenylethylamine (28 ul, 0.22 mmol) and DIEA (diisopropylethylamine) (0.11 mL, 0.44 mmol) in acetonitrile (2 mL) was stirred under at 80° C. for 4 h. After cooling to room temperature, the solid was collected by filtration, washed with a little bit of acetonitrile and dried. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-5% methanol in methylene chloride in 30 min) afforded 4-ethoxy-6-[2-[2-(3-fluoro-phenyl)-ethylamino]-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (60 mg, 67%) as a light yellow solid: LC-MS m/e 447 (MH+).

Provenance & Evidence