Potassium Carbonate → HCID 178486249, compound

Participants

Reaction Conditions

Reaction Steps

193 mg (1.39 mmol) of potassium carbonate, followed by 240 mg (0.87 mmol) of 4-morpholin-4-ylmethylbenzoyl chloride hydrochloride, are added to a solution of 0.27 g (0.70 mmol) of tert-butyl 3-amino-5-(N′-methyl-N′-phenylhydrazinocarbonyl)-thieno[2,3-c]pyrazole-1-carboxylate in 20 mL of tetrahydrofuran under argon. The reaction mixture is stirred at a temperature in the region of 25° C. for 2 hours, and then refluxed for 4 hours. The reaction mixture is then cooled to a temperature in the region of 25° C., and then treated with 40 mL of ice-cold water. The mixture is extracted successively with 60 mL, and then with twice 40 mL of ethyl acetate. The organic phases are combined, washed twice with 40 mL of saturated brine, dried over magnesium sulfate, filtered and then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C. The residue is purified by chromatography on a cartridge of 25 g of silica gel (0.015-0.040 mm), eluting successively with pure dichloromethane, and then with dichloromethane/methanol mixtures (99/1 by volume, and then 98.5/1.5, 98/2 and finally 97/3) at a flow rate of 10 mL/min. The fractions containing the expected product are combined and then concentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 30° C. 0.1 g of N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]-4-morpholin-4-ylmethylbenzamide is thus obtained in the form of an off-white solid melting at 190° C.

Provenance & Evidence