Ethyl Acetate → HCID 178430317, compound

Participants

Reaction Conditions

Reaction Steps

40 mg (108 μmol) of tetrabutylammonium iodide, followed by 184 mg (1.61 mmol) of cis-2,6-dimethylpiperazine, are added to a solution of 290 mg (0.54 mmol) of an approximately 70:30 mixture of tert-butyl 3-(4-chloromethylbenzoylamino)-5-(N′-methyl-N′-phenylhydrazinocarbonyl)thieno[2,3-c]pyrazole-1-carboxylate and tert-butyl 3-(4-chloromethylbenzoylamino)-5-(N′-(4-chlorophenyl)-N′-methylhydrazinocarbonyl)thieno[2,3-c]pyrazole-1-carboxylate in 6 mL of dimethylformamide under argon. The reaction mixture is stirred at a temperature in the region of 25° C. for 3 hours, and then poured into a mixture of ice, ethyl acetate and n-heptane. The mixture is filtered on a sinter funnel, suction-filtered and air-dried. The solid obtained is dissolved in 5 mL of methanol and the solution is introduced into a microwave oven tube. The tube is stoppered and the reaction mixture is irradiated at a temperature in the region of 100° C. for three times 10 minutes. The reaction mixture is then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C. The residue is purified by preparative LC/MS (condition B′). 130 mg of 4-(3,5-dimethylpiperazin-1-ylmethyl)-N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]benzamide are thus obtained in the form of a yellow powder melting between 192 and 202° C. LC-MS-DAD-ELSD: 518(+)=(M+H)(+).

Provenance & Evidence