HCID 178418361, compound → HCID 178508052, compound

HRID 1012051Notes

Reaction equation

HRID 1012051 reaction equation
[N+:1]([C:4]1[C:5]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)=[N:6][NH:7][CH:8]=1)([O-])=O.[H][H]>CN(C=O)C.[Pd]>[NH:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[C:5]1[C:4]([NH2:1])=[CH:8][NH:7][N:6]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178526862HCID 178526862, compound

Product 1

HCID 178508052HCID 178508052, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-nitro-1H-pyrazol-3-yl)-1H-benzimidazole (1.34 g, 5.85 mmol) and 10% Pd/C (0.13 g) in DMF (200 ml) was subjected to an atmosphere of hydrogen at room temperature for 36 h. The reaction mixture was filtered through a plug of Celite and reduced in vacuo. The residue was partitioned between EtOAc and water and the organic portion dried (MgSO4), filtered and reduced in vacuo. The residue was azeotroped with toluene (3×150 ml) yielding 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine as a purple solid (0.32 g, 26%). (LC/MS: Rt 0.97, [M+H]+ 199.62).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. customThe residue was partitioned between EtOAc and water
  3. dry with materialthe organic portion dried (MgSO4)
  4. filtrationfiltered
  5. customThe residue was azeotroped with toluene (3×150 ml)

Sources & evidence

ORD record
ord-11ca7e193bd14aef8ad2892872955077
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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