HCID 178526863, compound → HCID 178508053, compound

HRID 2182354Notes

Reaction equation

HRID 2182354 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7]([C:9]3[C:13]([N+:14]([O-])=O)=[CH:12][NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1>C(O)C.[Pd]>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7]([C:9]3[C:13]([NH2:14])=[CH:12][NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 178526863HCID 178526863, compound

Product 1

HCID 178508053HCID 178508053, compoundYield 143.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-chloro-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole [91 mg, Example 239(a)] in ethanol (40 mL), under nitrogen, was treated with palladium on carbon (spatula tip, 5%). The mixture was stirred under hydrogen for 3 hours and then filtered through Celite. The filter pad was washed well with dichloromethane. The combined filtrate and washings were evaporated to give 3-(5-chloro-1H-benzoimidazol-2-yl)-1H-pyrazol-4-ylamine (116 mg). LC-MS (METHOD A): RT=2 minutes; 234 (M+H)+. (b) 3-(5,6-Dichloro-1H-benzoimidazol-2-yl)-1H-pyrazol-4-ylamine

Workup

  1. filtrationfiltered through Celite
  2. washThe filter pad was washed well with dichloromethane
  3. customThe combined filtrate and washings were evaporated

Sources & evidence

ORD record
ord-36800c202fb040ad807466d379393167
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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