Potassium Carbonate → HCID 69355779, compound

HRID 1271281Notes

Reaction equation

HRID 1271281 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]([CH2:21][C@@H:22]([C:24]3[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=3)[OH:23])[CH3:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:32][C:33]([O:35][CH3:36])=[O:34].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[I-].[K+]>[CH3:36][O:35][C:33](=[O:34])[CH2:32][O:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([C@@H:22]([OH:23])[CH2:21][N:19]([C:10]2[CH:9]=[N:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:11]=2)[CH3:20])[CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 69354999HCID 69354999, compound

Product 1

HCID 69355779HCID 69355779, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.66 g of (R)-3-{2-[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]-1-hydroxyethyl}phenol and 0.28 g of methyl bromoacetate in 10 ml of acetonitrile, 2 mg of potassium iodide and 0.28 g of potassium carbonate were added and the mixture was heated at reflux for 4 hours. The insoluble matter was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.55 g of the desired compound as a pale orange amorphous.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe insoluble matter was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6887e6c3779e4e7fbcd9bd5d5c3972f5
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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