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Methyl iodide → HCID 68006317, Verbindung

HRID 1026601
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1026601
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:25])[N:9]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:4][CH:3]=1.[H-].[Na+].[C:28](=O)([O:32]CC)[O:29][CH2:30][CH3:31].[CH3:36]I>O.O1CCCC1>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([N:9]2[C:10]3[C:5](=[N:4][CH:3]=[C:2]([Cl:1])[CH:11]=3)[CH2:6][C:7]([CH3:36])([C:28]([O:29][CH2:30][CH3:31])=[O:32])[C:8]2=[O:25])[CH2:13][CH2:14]1)=[O:19])([CH3:22])([CH3:24])[CH3:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 68006101HCID 68006101, Verbindung

Produkt 1

HCID 68006317HCID 68006317, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a tetrahydrofuran solution (10 ml) of tert-butyl 4-(7-chloro-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (Reference Example 9-3) (500 mg) were added at 0° C. sodium hydride (161 mg) and diethyl carbonate (0.66 ml). After the reaction solution was stirred at 70° C. for 4 hours, methyl iodide (0.171 ml) was added at 0° C., and stirred at room temperature for 6 hours. Water was added to the reaction solution at 0° C., and extracted with ethyl acetate. The collected organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford ethyl 1-[1-(tert-butoxycarbonyl)piperidin-4-yl]-7-chloro-3-methyl-2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridine-3-carboxylate (286 mg).

Aufarbeitung

  1. stirringstirred at room temperature for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe collected organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5ab51403f85043b695cb61c7829a27f5
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729095B2

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