Potassium Carbonate → HCID 22989230, compound

HRID 1169054Notes

Reaction equation

HRID 1169054 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][S:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([N:14]=[CH:15][N:16]=2)[N:13]=1.[C:17]1([CH:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:37](=[O:40])([O-:39])[O-].[K+].[K+]>CN(C)C=O>[C:23]([OH:4])(=[O:24])/[CH:31]=[CH:36]/[C:37]([OH:39])=[O:40].[C:31]1([CH:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][S:7][C:8]3[CH:9]=[CH:10][C:11]4[N:12]([N:14]=[CH:15][N:16]=4)[N:13]=3)[CH2:27][CH2:26]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30175844-BenzhydryloxypiperidineHCID 22989309HCID 22989309, compound

Product 1

HCID 22989230HCID 22989230, compoundYield 121.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.35 g of 6-[2-(2-bromoethoxy)ethylthio][1,2,4]triazolo[1,5-b]pyridazine and 1.19 g of 4-(diphenylmethoxy)piperidine were dissolved in 15 ml of N,N-dimethylformamide, 740 mg of potassium carbonate was added, followed by stirring at room temperature for 17 hours. Ice water was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol (10:1). The desired fraction was collected; the residue was dissolved in 10 ml of ethanol; 360 mg of fumaric acid was added, followed by concentration. Ethyl ether was added to the residue; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 1.64 g of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe extract was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate:methanol (10:1)
  6. customThe desired fraction was collected
  7. dissolutionthe residue was dissolved in 10 ml of ethanol
  8. addition360 mg of fumaric acid was added
  9. concentrationfollowed by concentration
  10. additionEthyl ether was added to the residue
  11. customthe crystal precipitated
  12. filtrationwas collected by filtration
  13. washwashed with ethyl ether
  14. customdried

Sources & evidence

ORD record
ord-58cd8dbab22143d1abd78f79fe43e52a
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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