5-(1-Methyl-1-phenyl-ethylcarbamoyl)-3-(2-nitro-benzoylamino)-thieno[2,3-c]pyrazole-1-carboxylic Acid ethyl Ester → 3-(2-Amino-benzoylamino)-5-(1-methyl-1-phenyl-ethylcarbamoyl)-thieno[2,3-c]pyrazole-1-carboxylic Acid ethyl Ester

HRID 549437Notes

Reaction equation

HRID 549437 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:10]2[S:11][C:12]([C:14](=[O:25])[NH:15][C:16]([CH3:24])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])=[CH:13][C:9]=2[C:8]([NH:26][C:27](=[O:37])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N+:34]([O-])=O)=[N:7]1)=[O:5])[CH3:2]>C(OC(=O)C)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[C:10]2[S:11][C:12]([C:14](=[O:25])[NH:15][C:16]([CH3:24])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])=[CH:13][C:9]=2[C:8]([NH:26][C:27](=[O:37])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[NH2:34])=[N:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 577372605-(1-Methyl-1-phenyl-ethylcarbamoyl)-3-(2-nitro-benzoylamino)-thieno[2,3-c]pyrazole-1-carboxylic Acid ethyl Ester

Product 1

HCID 577372693-(2-Amino-benzoylamino)-5-(1-methyl-1-phenyl-ethylcarbamoyl)-thieno[2,3-c]pyrazole-1-carboxylic Acid ethyl EsterYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The suspension of 1.8 g (3.451 mmol) of 5-(1-Methyl-1-phenyl-ethylcarbamoyl)-3-(2-nitro-benzoylamino)-thieno[2,3-c]pyrazole-1-carboxylic acid ethyl ester and 500 mg of Pd/C (10%) in 45 mL of ethylacetate was shaken under hydrogen pressure (40 psi). The catalyst was renewed (500 mg) after 8 hours and the mixture treated for further 8 hours. The catalyst was then filtered over a celite pad and the solvent removed under vacuum. The crude was purified on silica gel (eluant dichloromethane-methanol 98:2) yielding 1.44 g (85%) of the title compound.

Workup

  1. customafter 8 hours
  2. additionthe mixture treated for further 8 hours
  3. filtrationThe catalyst was then filtered over a celite pad
  4. customthe solvent removed under vacuum
  5. customThe crude was purified on silica gel (eluant dichloromethane-methanol 98:2)

Sources & evidence

ORD record
ord-627428405107429baaf85ccb381a9425
Source dataset
uspto-grants-2011_05
Patent number
US07943654B2

Reaction notes

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