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Ethyl Acetate → 3-[3-(2-Fluorophenoxymethyl)pyrrolidino]methyl-1H-pyrazin-2-one oxalate

HRID 914880
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 914880
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[C:13]([O:18]C)=[N:14][CH:15]=[CH:16][N:17]=2)[CH2:7]1.[C:24](=[O:27])([OH:26])[O-].[Na+].[C:29]([O:32]CC)(=[O:31])C>C(O)C.Cl.C(OCC)(=O)C>[C:29]([OH:32])(=[O:31])[C:24]([OH:26])=[O:27].[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[C:13](=[O:18])[NH:14][CH:15]=[CH:16][N:17]=2)[CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 222479393-[3-(2-Fluorophenoxymethyl)pyrrolidino]methyl-2-methoxypyrazine

Produkt 1

HCID 222485423-[3-(2-Fluorophenoxymethyl)pyrrolidino]methyl-1H-pyrazin-2-one oxalateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 21866389Hydrogen chloride-ethyl acetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

After dissolving 245 mg of 3-[3-(2-fluorophenoxymethyl)pyrrolidino]methyl-2-methoxypyrazine in 5 ml of ethanol, 15 ml of 4N hydrogen chloride/ethyl acetate was added, and the mixture was heated to reflux for 8 hours and then stirred overnight at 60° C. Aqueous sodium bicarbonate solution was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol). This was dissolved in a small amount of ethanol, and then 47 mg of oxalic acid anhydrous and ethyl acetate were added and the precipitate was filtered out to obtain the title compound (171 mg, 56% yield).

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 8 hours
  4. washThe organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol)
  8. dissolutionThis was dissolved in a small amount of ethanol
  9. addition47 mg of oxalic acid anhydrous and ethyl acetate were added
  10. filtrationthe precipitate was filtered out

Quellen und Nachweise

ORD-Eintrag
ord-9057efa451424d2a958fb822e3d12f45
Quelldatensatz
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07265108B2

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