Pyridine → HCID 58096630, compound

HRID 1971033Notes

Reaction equation

HRID 1971033 reaction equation
[CH:1]1[CH:2]=[C:3]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]4[CH2:30][CH2:29][C:27](=[O:28])[NH:26][C:24]=4[CH:25]=3)[CH2:11][CH2:10]2)[C:4]([Cl:8])=[C:5]([Cl:7])[CH:6]=1.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH:32]=[O:33].C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1.[C:50](Cl)(=[O:60])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CO.ClCCl>[C:50]([O:33][CH:32]([N:26]1[C:24]2[C:23](=[CH:22][CH:21]=[C:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][N:9]([C:3]4[CH:2]=[CH:1][CH:6]=[C:5]([Cl:7])[C:4]=4[Cl:8])[CH2:10][CH2:11]3)[CH:25]=2)[CH2:30][CH2:29][C:27]1=[O:28])[C:31]([O:35][CH2:36][CH3:37])=[O:34])(=[O:60])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59]

Participants

9

Reactant 5

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 60795AripiprazoleHCID 66982Decanoyl chlorideHCID 70211Ethyl oxoacetate

Product 1

HCID 58096630HCID 58096630, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of Aripiprazole (2.0 g, 4.5 mmol), ethyl glyoxylate (50% soln. in toluene, 2.7 mL), K2CO3 (0.49 g, 3.6 mmol), tetrabutylammonium bromide (0.57 g, 1.8 mmol) and dichloromethane (20 mL) was heated at reflux for 4 h. The reaction mixture was cooled and quickly washed with water, dried over MgSO4 and filtered. The resulting solution was treated with pyridine (1.8 mL, 22.2 mmol) and then decanoylchloride (4.6 mL, 22.2 mmol). After being stirred for 3 h, methanol (1 mL) was added and stirred a further 10 min. The reaction mixture was washed with sat. NaHCO3 (aq), dried over MgSO4 and evaporated. The residue was purified on silica eluting with 1:1:0.1 dichloromethane/ethyl acetate/methanol to give the title compound as a yellow oil (1.2 g, 38%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction mixture was cooled
  4. washquickly washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. stirringstirred a further 10 min
  8. washThe reaction mixture was washed with sat. NaHCO3 (aq)
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customThe residue was purified on silica eluting with 1:1:0.1 dichloromethane/ethyl acetate/methanol

Sources & evidence

ORD record
ord-3618d60f270b4965b67036fd9f485cfa
Source dataset
uspto-grants-2013_04
Patent number
US08431576B2

Reaction notes

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