Sodium Chloride → 2-{5-Bromo-6-oxo-4-[2-(tricyclo[3.3.1.13,7]dec-1-yl)ethoxy]pyridazin-1(6H)-yl}-N-(pyridin-4-ylmethyl)acetamide

HRID 2092122

Reaktionsgleichung

Reaktionsgleichung von HRID 2092122
Br[C:2]1[CH:3]=[N:4][N:5]([CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[O:12])[C:6](=[O:9])[C:7]=1[Br:8].[C:21]12([CH2:31][CH2:32][OH:33])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2.[OH-].[Na+].[Cl-].[Na+]>O1CCOCC1>[Br:8][C:7]1[C:6](=[O:9])[N:5]([CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[O:12])[N:4]=[CH:3][C:2]=1[O:33][CH2:32][CH2:31][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 1108102-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanolHCID 595743872-(4,5-Dibromo-6-oxopyridazin-1(6H)-yl)-N-(pyridin-4-ylmethyl)acetamide

Produkt 1

HCID 595742432-{5-Bromo-6-oxo-4-[2-(tricyclo[3.3.1.13,7]dec-1-yl)ethoxy]pyridazin-1(6H)-yl}-N-(pyridin-4-ylmethyl)acetamideAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-{4,5-Dibromo-6-oxopyridazin-1(6H)-yl}-N-(pyridin-4-ylmethyl)acetamide (48 mg, 0.119 mmol) and 1-adamantanethanol (92 mg, 0.510 mmol) in 1,4-dioxane (2 mL) were stirred with 6 M aqueous sodium hydroxide (50 μL, 0.300 mmol) at 100° C. for 6 hours. After completion of the reaction, the reaction solution was mixed with saturated aqueous sodium chloride and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 0/1) to give the desired product (9% yield).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 0/1)

Quellen und Nachweise

ORD-Eintrag
ord-86aa0ebb52f648828c59f76f96808ec1
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440666B2

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