N-Aminomorpholine → 1-(2-chloro-phenyl)-5-(4-chlorophenyl)-4-methoxy-3-(N-morpholinocarbamoyl)-1H-pyrazole

Participants

Reaction Steps

To a solution of 3-carboxy-1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methoxy-1H-pyrazole (3.5 g, compound obtained in Reference Example 1(6)) in methylene chloride (100 mL) was added N-aminomorpholine (1.47 g), water-soluble carbodiimide HCl (2.76 g) and 1-hydroxybenzotriazole hydrate (2.21 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added an aqueous sodium hydrogencarbonate solution and the mixture was stirred and extracted with chloroform. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=40/60 to 20/80) to obtain 1-(2-chloro-phenyl)-5-(4-chlorophenyl)-4-methoxy-3-(N-morpholinocarbamoyl)-1H-pyrazole (3.49 g; yield: 81%) as a powder.

Provenance & Evidence