HCID 11044975, compound → HCID 18763022, compound

HRID 840098Notes

Reaction equation

HRID 840098 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([N+:21]([O-])=O)=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2]>C1COCC1.[Pd]>[NH2:21][C:19]1[CH:18]=[CH:17][C:14]2[N:15]([CH3:16])[C:11]([CH2:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[N:12][C:13]=2[CH:20]=1

Participants

4

Reactant 1

HCID 11044975HCID 11044975, compound

Product 1

HCID 18763022HCID 18763022, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-5-nitro-benzimidazole (5.5 g, 18 mmol) in 150 mL THF/75 mL methanol is hydrogenated in the presence of 1.0 g of 5% Pd/C at ambient temperature and normal pressure. The catalyst is filtered off, the filtrate is evaporated down until not completely dry, diluted with 100 mL acetonitrile and evaporated down to a residual volume of 30 mL. The crystal slurry is cooled and filtered. The crystals are washed with cold acetonitrile and ether.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated down until not
  3. customcompletely dry
  4. additiondiluted with 100 mL acetonitrile
  5. customevaporated down to a residual volume of 30 mL
  6. temperatureThe crystal slurry is cooled
  7. filtrationfiltered
  8. washThe crystals are washed with cold acetonitrile and ether

Sources & evidence

ORD record
ord-592fd8fed26c4641a81ef327323958c6
Source dataset
uspto-grants-2002_04
Patent number
US06365584B1

Reaction notes

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