Water → HCID 66792904, compound

HRID 535006Notes

Reaction equation

HRID 535006 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][CH2:28][NH:27][C:26]3=[O:30])=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].O>CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][CH2:28][N:27]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:26]3=[O:30])=[CH:21][CH:20]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 66751070HCID 66751070, compound

Product 1

HCID 66792904HCID 66792904, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}phenyl)imidazolidin-2-one (1.0 g, 2.46 mmol) and sodium hydride (0.16 g, 4.0 mmol) in N,N-dimethylformamide (20 mL) was stirred at 0° C. for 1 h. tert-Butyl bromoacetate was added to the reaction mixture and the mixture was stirred at room temperature for 3 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a solid (1.3 g, quant.).

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a solid (1.3 g, quant.)

Sources & evidence

ORD record
ord-cbe1c668f05f440f9102a98ffd78a06f
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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