Methyl iodide → 4-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]-1-methylpiperazin-2-one

HRID 389991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389991
[H-].[Na+].[CH2:3]([C:5]1[C:27]([F:28])=[CH:26][C:8]([O:9][C:10]2[CH:24]=[CH:23][C:13]([C:14]([N:16]3[CH2:21][CH2:20][NH:19][C:18](=[O:22])[CH2:17]3)=[O:15])=[CH:12][C:11]=2[F:25])=[C:7]([O:29][CH3:30])[CH:6]=1)[CH3:4].IC.[C:33](OCC)(=O)C>CN(C)C=O.O>[CH2:3]([C:5]1[C:27]([F:28])=[CH:26][C:8]([O:9][C:10]2[CH:24]=[CH:23][C:13]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([CH3:33])[C:18](=[O:22])[CH2:17]3)=[O:15])=[CH:12][C:11]=2[F:25])=[C:7]([O:29][CH3:30])[CH:6]=1)[CH3:4]

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 671162484-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

Produkt 1

HCID 671162384-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]-1-methylpiperazin-2-oneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in oil, 25 mg, 0.6 mmol) was added to a solution of 4-[4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoy]-piperazin-2-one (which may be prepared in accordance with the experimental described in Example 5, step 1; 200 mg, 0.5 mmol) in N,N-dimethylformamide (5 mL). The reaction mixture was stirred at room temperature for 15 minutes prior to the addition of iodomethane (0.48 mL, 0.77 mmol). After stirring at room temperature for 1 hour, the reaction mixture was diluted by addition of ethyl acetate (30 mL) and water (30 mL). The two phases were separated and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic phases were finally washed with a saturated solution of sodium chloride (5×20 mL), dried over sodium sulfate, filtered and concentrated under vacuum to afford the title product as a yellow oil (200 mg, 97%).

Aufarbeitung

  1. custommay be prepared in accordance with the
  2. stirringAfter stirring at room temperature for 1 hour
  3. customThe two phases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
  5. washThe combined organic phases were finally washed with a saturated solution of sodium chloride (5×20 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d5257bc648f84e18a20f56bac4361c3b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383621B2

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