HCID 178432831, compound → HCID 178432830, compound

HRID 2409249Notes

Reaction equation

HRID 2409249 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[N:12][C:11]=2[CH3:20])=[CH:4][C:3]=1[C:22]1[NH:26][C:25]2[CH:27]=[CH:28][C:29]([N+:31]([O-])=O)=[CH:30][C:24]=2[N:23]=1>C(O)C.Cl.[Pd]>[NH2:31][C:29]1[CH:28]=[CH:27][C:25]2[NH:26][C:22]([C:3]3[CH:4]=[C:5]([NH:8][C:9](=[O:21])[C:10]4[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[N:12][C:11]=4[CH3:20])[CH:6]=[CH:7][C:2]=3[Cl:1])=[N:23][C:24]=2[CH:30]=1

Participants

5

Reactant 1

HCID 178432831HCID 178432831, compound

Product 1

HCID 178432830HCID 178432830, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[4-chloro-3-(5-nitro-1H-benzoimidazol-2-yl)-phenyl]-2-methyl-6-trifluoromethyl-nicotinamide (212 mg; 0.45 mmol) was dissolved in ethanol (4 ml) with 2 drops of concentrated hydrochloric acid. This was added to 5% palladium on charcoal (42 mg; 20 wt %) and the reaction stirred under an atmosphere of hydrogen for 3 hours. The catalyst was removed by filtering through celite and then the solvent by evaporation to leave N-[3-(5-amino-1H-benzoimidazol-2-yl)-4-chloro-phenyl]-2-methyl-6-trifluoromethyl-nicotinamide (198 mg, 100%).

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through celite
  3. customthe solvent by evaporation

Sources & evidence

ORD record
ord-8a7e02d350f44f758fd4ebb56c0cc250
Source dataset
uspto-grants-2014_08
Patent number
US08815895B2

Reaction notes

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