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Hydrochloric Acid → 7-(4-(benzyloxy)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1750074
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750074
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[N:19]=[C:18]([NH:20][C:21](=[O:26])C(C)(C)C)[C:17]([CH2:27][CH2:28]C(OCC)=O)=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[N:19]=[C:18]2[C:17]([CH2:27][CH2:28][C:21](=[O:26])[NH:20]2)=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66631318Ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)propanoate

Produkt 1

HCID 666339287-(4-(benzyloxy)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-oneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-Dioxane
Lösungsmittel

Versuchsvorschrift

To a solution of intermediate 9 (1.76 g, 3.9 mmol) in 1,4-dioxane (14 mL) was added 3N HCl (7.1 mL) and the mixture was then heated to reflux for 3 h. The mixture was cooled to rt and then anhydrous K2CO3 was slowly added to neutralize the reaction mixture to pH=8, then extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel column (elution with PE/EtOAc=4:1-1:1) to give 7-(4-(benzyloxy)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one (intermediate 10) (671 mg, 54%) as an oil.

Aufarbeitung

  1. temperaturethe mixture was then heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel column (elution with PE/EtOAc=4:1-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7cad54a6ab204ed7adb6c215fd30d0dc
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156822B2

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