HCID 53772538, compound → HCID 15104388, compound

HRID 1736818Notes

Reaction equation

HRID 1736818 reaction equation
C([O:8][C:9]1[C:14]2[N:15]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]#[N:36])=[CH:25][CH:24]=3)[C:16]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:17][C:13]=2[C:12]([CH3:37])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH2:18]([C:16]1[N:15]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH2:35][NH2:36])=[CH:27][CH:28]=2)[C:14]2[C:9]([OH:8])=[CH:10][CH:11]=[C:12]([CH3:37])[C:13]=2[N:17]=1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 53772538HCID 53772538, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15104388HCID 15104388, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.3 g (7.1 mmol) of 4'-[(7-benzyloxy-2-n-butyl-4-methyl-benzimidazol-1-yl)-methyl]-2-cyano-biphenyl are dissolved in 100 ml of methanol and hydrogenated at ambient temperature in the presence of 0.5 g of palladium (10% on carbon) at 5 bar of hydrogen. After 3 hours the catalyst is filtered off. 20 ml of 20% strength ammonia in methanol is added to the filtrate and the mixture is hydrogenated again at 70 ° C. in the presence of 0.5 g of Raney nickel at 5 bar of hydrogen. After 4 hours the catalyst is filtered off under suction and the filtrate is evaporated to dryness in vacuum. The crude crystalline product is suspended in ether, filtered under suction, washed using ether and dried in vacuum.

Workup

  1. filtrationAfter 3 hours the catalyst is filtered off
  2. addition20 ml of 20% strength ammonia in methanol is added to the filtrate
  3. customis hydrogenated again at 70 ° C. in the presence of 0.5 g of Raney nickel at 5 bar of hydrogen
  4. filtrationAfter 4 hours the catalyst is filtered off under suction
  5. customthe filtrate is evaporated to dryness in vacuum
  6. filtrationfiltered under suction
  7. washwashed
  8. customdried in vacuum

Sources & evidence

ORD record
ord-658a63a8fa1e4413b3c47e8ff06d8e02
Source dataset
uspto-grants-1996_07
Patent number
US05541229

Reaction notes

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