Reaction SMILES: [CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:16][C:17]1[CH:51]=[CH:50][C:20]([C:21]([NH:23][C:24]2[C:25]3[CH:38]=[C:37]([C:39]([NH:41][N:42]([CH3:49])[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[O:40])[S:36][C:26]=3[N:27](C(OC(C)(C)C)=O)[N:28]=2)=[O:22])=[CH:19][CH:18]=1.ClCC1C=CC(C(NC2C3C=C(C(NN(C4C=CC(Cl)=CC=4)C)=O)SC=3N(C(OC(C)(C)C)=O)N=2)=O)=CC=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([NH:23][C:24]2[C:25]3[CH:38]=[C:37]([C:39]([NH:41][N:42]([CH3:49])[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[O:40])[S:36][C:26]=3[NH:27][N:28]=2)=[O:22])=[CH:50][CH:51]=1)[CH3:2]
Reactant: CCN(CC)CCN
Reactant: CN(NC(=O)c1cc2c(NC(=O)c3ccc(CCl)cc3)nn(C(=O)OC(C)(C)C)c2s1)c1ccccc1
Agent: CCCC[N+](CCCC)(CCCC)CCCC
Agent: CN(NC(=O)c1cc2c(NC(=O)c3ccc(CCl)cc3)nn(C(=O)OC(C)(C)C)c2s1)c1ccc(Cl)cc1
Agent: O=C([O-])[O-]
Solvent: CN(C)C=O
Product: CCN(CC)CCNCc1ccc(C(=O)Nc2n[nH]c3sc(C(=O)NN(C)c4ccccc4)cc23)cc1
Temperature: 25 °C
Reaction time: 16 h

Procedure:
27 mg (74 μmol) of tetrabutylammonium iodide, 156 μL (1.11 mmol) of N,N-diethylethylenediamine and 153 mg (1.11 mmol) of potassium carbonate are successively added to a solution of 200 mg (0.37 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 16 hours, and then poured onto ice. It is then extracted twice with a 50/50 mixture of ethyl acetate and heptane. The organic extracts are combined, dried over magnesium sulfate and then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C. The residue is dissolved in 4 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 30 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 (conditions B). The fractions containing the expected products are combined and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is repurified by chromatography on a cartridge of 4 g of silica gel (0.035-0.060 mm), eluting with a dichloromethane/methanol mixture and then with a mixture of dichloromethane and methanol/28% aqueous ammonia (85/15 by volume). The fractions containing the expected products are combined and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 8 mg of 4-[(2-diethylaminoethylamino)methyl]-N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]benzamide are thus obtained in the form of a pale yellow powder melting from 143 to 150° C. LC-MS-DAD-ELSD: 520(+)/ . . . =(M+H)(+)/ . . . (1 Cl).