Hydrazine → HCID 178480689, compound

HRID 736289Notes

Reaction equation

HRID 736289 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:29]=[CH:28][C:11]([C:12]([NH:14][C:15]3[C:16]4[CH:22]=[C:21]([C:23]([O:25]CC)=O)[S:20][C:17]=4[NH:18][N:19]=3)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:30][NH2:31].O.NN>C(O)C>[NH:30]([C:23]([C:21]1[S:20][C:17]2[NH:18][N:19]=[C:15]([NH:14][C:12](=[O:13])[C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:29][CH:28]=3)[C:16]=2[CH:22]=1)=[O:25])[NH2:31]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 178468542HCID 178468542, compound

Product 1

HCID 178480689HCID 178480689, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-[4-(4-methylpiperazin-1-yl)benzoylamino]-1H-thieno[2,3-c]pyrazole-5-carboxylate (0.5 g, 1.03 mmol, 1 eq.) and ethanol (2 mL) are placed in a 15 mL round-bottomed flask, and a 1 M hydrazine solution (3.09 mL, 3.09 mmol) and 2 mL of hydrazine monohydrate are added. The reaction mixture is stirred at reflux for 5 hours, the solvent is then evaporated off and the residue is taken up in water. The white precipitate is filtered off, washed with water and then dried at a temperature in the region of 80° C. under vacuum. N-(5-Hydrazinocarbonyl-1H-thieno[2,3-c]pyrazol-3-yl)-4-(4-methylpiperazin-1-yl)benzamide (0.15 g, 49%), Rf=0.32 (methanol/dichloromethane 10/90 (v/v)) is thus obtained, which product is used directly in the following step. Ethyl 3-[4-(4-methylpiperazin-1-yl)benzoylamino]-1H-thieno[2,3-c]pyrazole-5-carboxylate may be obtained by deprotection of ethyl 1-(1-ethoxyethyl)-3-[4-(4-methylpiperazin-1-yl)benzoylamino]-1H-thieno[2,3-c]pyrazole-5-carboxylate according to example 28.

Workup

  1. temperatureat reflux for 5 hours
  2. customthe solvent is then evaporated off
  3. filtrationThe white precipitate is filtered off
  4. washwashed with water
  5. customdried at a temperature in the region of 80° C. under vacuum

Sources & evidence

ORD record
ord-a4500099bb10493fb332d268b3fce9c6
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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