HCID 69719549, compound → HCID 22349367, compound

HRID 896381Notes

Reaction equation

HRID 896381 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]2[N:7]([CH2:15][CH2:16][CH2:17][CH2:18][F:19])[C:8]([CH2:10][O:11]C(=O)C)=[N:9][C:5]=2[CH:4]=1)#[N:2]>CO.CCO.Cl.[Pd]>[NH2:2][CH2:1][C:3]1[CH:21]=[CH:20][C:6]2[N:7]([CH2:15][CH2:16][CH2:17][CH2:18][F:19])[C:8]([CH2:10][OH:11])=[N:9][C:5]=2[CH:4]=1

Participants

6

Reactant 1

HCID 69719549HCID 69719549, compound

Product 1

HCID 22349367HCID 22349367, compoundYield 28.3%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of acetic acid 5-cyano-1-(4-fluoro-butyl)-1H-benzoimidazol-2-ylmethyl ester (1.3 g, 4.5 mmol) in MeOH (50 ml), EtOH (10 ml), concentrated HCl (10 ml) and 10% Pd/C (100 mg) was hydrogenated for 2 h. The solution was filtered and concentrated. The residue was dissolved in EtOAc and washed with aq NaHCO3. The product remains in the aqueous layer. The water was removed and the residue washed with hot EtOAc. The EtOAc extracts are concentrated to give 0.32 g (18%) of [5-aminomethyl-1-(4-fluoro-butyl)-1H-benzoimidazol-2-yl]-methanol as a white solid.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with aq NaHCO3
  5. customThe water was removed
  6. washthe residue washed with hot EtOAc
  7. concentrationThe EtOAc extracts are concentrated

Sources & evidence

ORD record
ord-0e3b11ee058b4db4aa916ebb124156ee
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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