Dimethylformamide → HCID 57460771, compound

HRID 1718829Notes

Reaction equation

HRID 1718829 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[C:8](=[O:25])[NH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].CN(C)C=O.Br[CH2:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41]>C(OCC)(=O)C>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[C:8](=[O:25])[N:7]([CH2:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 21642BromopinacoloneHCID 149510524'-[(3-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)methyl]biphenyl-2-carbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 57460771HCID 57460771, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4′-[(3-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)methyl]biphenyl-2-carbonitrile (0.7 g), potassium tert-butoxide (1.0 M tetrahydrofuran solution, 1.75 mL) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 10 min, 1-bromo-3,3-dimethylbutan-2-one (0.22 mL) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogen sulfate solution and then 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 powder (0.58 g, 92%).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. washwashed with 5% aqueous potassium hydrogen sulfate solution
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a0bb044fdce04416b87d3f0d9d7c9262
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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