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 2092122Notes

Reaction equation

HRID 2092122 reaction equation
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

Participants

6

Reactant 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

Product 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)acetamideYield 9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-86aa0ebb52f648828c59f76f96808ec1
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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