Sodium borohydride → HCID 67009846, compound

HRID 1412152Notes

Reaction equation

HRID 1412152 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:38])[CH2:9][N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)=[C:13]([CH2:32][CH2:33][CH3:34])[N:12]3[N:35]=[CH:36][N:37]=[C:11]23)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:38])[CH2:9][N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)=[C:13]([CH2:32][CH2:33][CH3:34])[N:12]3[N:35]=[CH:36][N:37]=[C:11]23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67009035HCID 67009035, compound

Product 1

HCID 67009846HCID 67009846, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (15 mL) of 4′-({4-[2-(4-fluorophenyl)-2-oxoethyl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile (0.78 g) in methanol was added sodium borohydride (0.12 g), and the mixture was stirred at room temperature for 1 hr. After evaporation of the solvent under reduced pressure, the residue was extracted with water and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.78 g, 100%).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. extractionthe residue was extracted with water and ethyl acetate
  3. washThe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea01e6b094834d6ea4f1ba6207545d01
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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