Dimethylformamide → HCID 22989345, compound

HRID 1169052Notes

Reaction equation

HRID 1169052 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9]1[C:10]([CH3:18])=[CH:11][C:12]2[N:13]([N:15]=[CH:16][N:17]=2)[N:14]=1.[C:19]1([CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:26][CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:39](=[O:42])([O-:41])[O-].[K+].[K+].CN(C)C=[O:48]>>[C:25]([OH:48])(=[O:26])/[CH:33]=[CH:38]/[C:39]([OH:41])=[O:42].[C:33]1([CH:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:26][CH:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9]3[C:10]([CH3:18])=[CH:11][C:12]4[N:13]([N:15]=[CH:16][N:17]=4)[N:14]=3)[CH2:29][CH2:28]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 30175844-BenzhydryloxypiperidineHCID 22989287HCID 22989287, compound

Product 1

HCID 22989345HCID 22989345, compound

Procedure

1.0 g of 6-(6-bromohexylthio)-7-methyl[1,2,4]triazolo[1,5-b]pyridazine and 810 mg of 4-(diphenylmethoxy)piperidine were dissolved in 10 ml of N,N-dimethylformamide; 500 mg of potassium carbonate was added, followed by stirring at room temperature for 24 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 and concentrated; the residue was dissolved in 10 ml of ethanol; 290 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 1.43 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. concentrationconcentrated
  8. dissolutionthe residue was dissolved in 10 ml of ethanol
  9. addition290 mg of fumaric acid was added
  10. concentrationfollowed by concentration
  11. additionEthyl ether was added to the residue
  12. customthe crystal precipitated
  13. filtrationwas collected by filtration
  14. washwashed with ethyl ether
  15. customdried

Sources & evidence

ORD record
ord-b422aa2d6da246469ac9d924116af2ef
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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