Potassium Carbonate → HCID 22989395, compound

HRID 1169053Notes

Reaction equation

HRID 1169053 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][S:7][C:8]1[C:9]([CH3:17])=[CH:10][C:11]2[N:12]([N:14]=[CH:15][N:16]=2)[N:13]=1.[C:18]1([CH:24]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:38](=[O:41])([O-:40])[O-].[K+].[K+]>CN(C)C=O>[C:24]([OH:4])(=[O:25])/[CH:32]=[CH:37]/[C:38]([OH:40])=[O:41].[C:32]1([CH:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][S:7][C:8]3[C:9]([CH3:17])=[CH:10][C:11]4[N:12]([N:14]=[CH:15][N:16]=4)[N:13]=3)[CH2:28][CH2:27]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30175844-BenzhydryloxypiperidineHCID 22989259HCID 22989259, compound

Product 1

HCID 22989395HCID 22989395, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.09 g of 6-[2-(2-bromoethoxy)ethylthio]-7-methyl[1,2,4]triazolo[1,5-b]pyridazine and 840 mg of 4-(diphenylmethoxy)piperidine were dissolved in 10 ml of N,N-dimethylformamide; 520 mg of potassium carbonate was added, followed by stirring at room temperature for 23 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 dichloromethane:ethyl acetate:methanol (5:5:1). The desired fraction was collected; the residue was dissolved in 10 ml of ethanol; 200 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 0.78 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 dichloromethane:ethyl acetate:methanol (5:5:1)
  6. customThe desired fraction was collected
  7. dissolutionthe residue was dissolved in 10 ml of ethanol
  8. addition200 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-55e151a7c1174b8580594288a25016b5
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

Loading…