4-Methylmorpholine → HCID 57550425, compound

Participants

Reaction Steps

Potassium hydroxide solution (2 M in water, 90 μL, 0.18 mmol) was added to a solution of [1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-3-oxo-4-(3-piperidin-1-yl-propyl)-piperazin-2-yl]-acetic acid ethyl ester (example 33; 92 mg, 0.18 mmol) in ethanol (1 ml). The reaction mixture was stirred at room temperature for 18 h, then after evaporation potassium [1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-3-oxo-4-(3-piperidin-1-yl-propyl)-piperazin-2-yl]-acetate was obtained. This was dissolved in N,N-dimethylformamide (1 ml), then dimethylamine hydrochloride (14 mg, 0.17 mmol), 4-methylmorpholine (81 mg, 0.99 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluoro-phosphate (92 mg, 0.24 mmol) were added. The reaction mixture was stirred for 16 h at room temperature, then partitioned between ethyl acetate and water. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; dichloromethane/methanol/ammonium hydroxide 90:10:0.25) afforded the title compound (73 mg, 79%). Off-white foam, MS (ISP)=509.1 (M+H)+.

Provenance & Evidence