Sodium borohydride → HCID 178511148, compound

HRID 1935724Notes

Reaction equation

HRID 1935724 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[NH:10][C:11]3[C:17]([C:18](=[O:22])[CH2:19][C:20]#[N:21])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:1]1([CH2:7][CH2:8][C:9]2[NH:10][C:11]3[C:17]([CH:18]([OH:22])[CH2:19][C:20]#[N:21])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178511147HCID 178511147, compound

Product 1

HCID 178511148HCID 178511148, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-(2-(2-Phenylethyl)benzimidazol-4-yl)3-oxopropionitrile (400 mg) obtained in Inventive Example 25 in ethanol (4.8 mL), while cooling in an ice bath, was added sodium borohydride (26 mg), and the mixture was stirred at the same temperature for 1 hour. The reaction solution was poured into ice water (20 mL) and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was crystallized from ether and collected by filtration to obtain the title compound as crystal (297 mg)

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe resulting residue was crystallized from ether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f981225ebde54970b419a032cc8ef632
Source dataset
uspto-grants-2002_05
Patent number
US06387938B1

Reaction notes

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