HCID 67099131, compound → HCID 23125737, compound

HRID 1454699Notes

Reaction equation

HRID 1454699 reaction equation
[Cl:1][C:2]1[C:3]([C:22]([F:25])([F:24])[F:23])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][C:19]#[N:20])=[N:16][CH:17]=3)[C:6]=2[CH:21]=1>N.C(O)C.[Ni]>[Cl:1][C:2]1[C:3]([C:22]([F:23])([F:24])[F:25])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][NH2:20])=[N:16][CH:17]=3)[C:6]=2[CH:21]=1

Participants

4

Reactant 1

HCID 67099131HCID 67099131, compound

Product 1

HCID 23125737HCID 23125737, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

To a solution of {5-[6-chloro-2-ethyl-5-(trifluoromehyl)-1H-benzimidazol-1-yl]-2-pyridinyl}acetonitrile (step 4, 1.0 g, 2.8 mmol), in ammonia-ethanol (30 ml) was added Raney-Ni and stirred for 8 h under hydrogen atmosphere (3.0 kgf/cm2) The catalyst was filtered off and the solvent was removed. The residue was diluted with ethyl acetate, washed with brine, dried (MgSO4) and concentrated to give 813 mg of title compound as black solid. MS (EI) m/z: 368 (M+).

Workup

  1. filtrationwas filtered off
  2. customthe solvent was removed
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6f3b5b0d68e14d34b030bab458c56a0c
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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