Sodium Chloride → HCID 23139199, compound

HRID 1171754Notes

Reaction equation

HRID 1171754 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.[C:33]([O:37][CH2:38][CH3:39])(=[O:36])[CH:34]=[CH2:35].N12CCCN=C1CCCCC2.[Cl-].[Na+]>C(#N)C>[CH2:38]([O:37][C:33]([CH2:34][CH2:35][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 8821Ethyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23138676HCID 23138676, compound

Product 1

HCID 23139199HCID 23139199, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (E)-3-[(1H-pyrazol-4-yl)methylidene]-1-(triphenylmethyl)piperidin-4-one (Example 98(a), 6.0 g) in acetonitrile (100 ml) were added ethyl acrylate (4.7 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (6.4 ml). The resulting mixture was stirred at room temperature for 15 minutes, and the reaction was stopped by an addition of a saturated aqueous sodium chloride solution. The products were extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and solvents were evaporated in vacuo. 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 (6.12 g, yield: 82%).

Workup

  1. extractionThe products were extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate, and solvents
  3. customwere 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-db9d6825faff48c2b6767973aed844a7
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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