HCID 11044975, compound → HCID 18763022, compound

HRID 2186886Notes

Reaction equation

HRID 2186886 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 5% Pd/C at ambient temperature and normal pressure. The catalyst is filtered off, the filtrate is evaporated down until not quite 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. customquite 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-12fb94ad28f942e4abc828345e7789e8
Source dataset
uspto-grants-2002_06
Patent number
US06407130B1

Reaction notes

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