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Dimethyl Sulfoxide → HCID 68006252, Verbindung

HRID 1026606
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1026606
CS(C)=O.Br[CH:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:16])=[CH:13][N:14]=2)[N:9]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[C:8](=[O:30])[C:7]1([CH3:32])[CH3:31].C(=O)([O-])[OH:34].[Na+]>O>[Cl:16][C:12]1[CH:11]=[C:10]2[C:15]([C:6](=[O:34])[C:7]([CH3:32])([CH3:31])[C:8](=[O:30])[N:9]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[N:14][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 68006085HCID 68006085, Verbindung

Produkt 1

HCID 68006252HCID 68006252, VerbindungAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a dimethylsulfoxide solution (8 ml) of tert-butyl 4-(4-bromo-7-chloro-3,3-dimethyl-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (375 mg) was added sodium hydrogen carbonate (871 mg), followed by stirring at 100° C. for 6 hours. Water was added to the reaction solution, and extracted with ethyl acetate. The collected organic layer was washed sequentially with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. After the resulting residue was dissolved in dichloromethane (14 ml), manganese dioxide (684 mg) was added and stirred for 50 minutes, and further manganese dioxide (690 mg) was added and stirred for 1 hour. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford tert-butyl 4-(7-chloro-3,3-dimethyl-2,4-dioxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (270 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe collected organic layer was washed sequentially with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionAfter the resulting residue was dissolved in dichloromethane (14 ml)
  6. additionmanganese dioxide (684 mg) was added
  7. stirringstirred for 50 minutes
  8. additionfurther manganese dioxide (690 mg) was added
  9. stirringstirred for 1 hour
  10. filtrationThe reaction mixture was filtered through Celite
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d4a0ff9cb1d24e4fa99cf9be234bb249
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729095B2

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