Ammonia → HCID 68512212, compound

HRID 1410204Notes

Reaction equation

HRID 1410204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[NH:10][C:11]1[N:15]([CH3:16])[C:14]2[CH:17]=[CH:18][C:19]([C:21]([NH:23][CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:22])=[CH:20][C:13]=2[N:12]=1.N>[Ni].CCO>[NH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([NH:23][CH2:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:22])=[CH:20][C:13]=3[N:12]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 68514060HCID 68514060, compound

Product 1

HCID 68512212HCID 68512212, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(2-chloro-5-cyanophenylamino)-N-cyclohexylmethyl-1-methylbenzimidazole-5-carboxamide (500 mg, 1.19 mmol, prepared in analogy to the experimental procedures described above) and EtOH (20 mL) was saturated with ammonia. Freshly prepared Raney-Nickel (7 mg, 0.12 mmol) was added and the mixture was hydrogenated (rt, 70 atm) for 48 h. The mixture was filtered through Celite and the filter cake washed with EtOAc. The combined filtrates were concentrated and the residue treated with a mixture of petroleum ether and diethyl ether to give the sub-title compound. Yield: 500 mg (98%).

Workup

  1. customprepared in analogy to the experimental procedures
  2. custom(rt, 70 atm)
  3. customfor 48 h
  4. filtrationThe mixture was filtered through Celite
  5. washthe filter cake washed with EtOAc
  6. concentrationThe combined filtrates were concentrated
  7. additionthe residue treated with a mixture of petroleum ether and diethyl ether

Sources & evidence

ORD record
ord-9ad7f7531bbe4404bc62e4da957cf072
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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