Sodium Chloride → HCID 23139093, compound

HRID 1171751Notes

Reaction equation

HRID 1171751 reaction equation
[NH:1]1[CH:5]=[C:4](/[CH:6]=[C:7]2\[CH2:8][N:9]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:11][C:12]\2=[O:13])[CH:3]=[N:2]1.Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].N12CCCN=C1CCCCC2.[Cl-].[Na+]>C(#N)C>[CH2:38]([O:37][C:35]([CH2:34][N:1]1[CH:5]=[C:4](/[CH:6]=[C:7]2\[CH2:8][N:9]([C:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:10][CH2:11][C:12]\2=[O:13])[CH:3]=[N:2]1)=[O:36])[CH3:39]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7748Ethyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23138676HCID 23138676, compound

Product 1

HCID 23139093HCID 23139093, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (E)-3-[(1H-pyrazol-4-yl)methylidene]-1-(triphenylmethyl)piperidin-4-one (6.0 g) in acetonitrile (100 ml) were added ethyl bromoacetate (7.2 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (6.4 ml). The resulting mixture was stirred at room temperature for one hour, and the reaction was stopped by addition of a saturated aqueous sodium chloride solution. The products were extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo, and the residue was purified by chromatography on silica gel using a mixture of hexane, ethyl acetate and dichloromethane (2:1:1) as the eluent to afford the title compound as a yellow amorphous solid (6.08 g, yield: 84%).

Workup

  1. extractionThe products were extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel using
  5. additiona mixture of hexane, ethyl acetate and dichloromethane (2:1:1) as the eluent

Sources & evidence

ORD record
ord-12285b1a5f2e4706a7ee53b3141c531d
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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