Potassium Iodide → HCID 23000344, compound

HRID 397558Notes

Reaction equation

HRID 397558 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[N:20][N:21]=2)[N:18]=1)(=O)=O.[C:22]1([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:35]1([CH:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:29]2[CH2:30][CH2:31][N:32]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]3[CH:14]=[CH:15][C:16]4[N:17]([CH:19]=[N:20][N:21]=4)[N:18]=3)[CH2:33][CH2:34]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 23000329HCID 23000329, compound

Product 1

HCID 23000344HCID 23000344, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

796 mg of 6-[6-(methanesulfonyloxy)hexylamino][1,2,4]triazolo[4,3-b]pyridazine was dissolved in 15 ml of N,N-dimethylformamide; 769 mg of 1-(diphenylmethyl)piperazine, 422 mg of potassium carbonate, and 506 mg of potassium iodide were added, followed by stirring at 60° C. for 4 hours. After cooling, saline was added; the reaction mixture was extracted with ethyl acetate and dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol-triethylamine (50:5:1). The desired fraction was collected and concentrated under reduced pressure; the residue was crystallized from ethyl acetate, washed with diethyl ether, recrystallized in the same manner, and dried, to yield 353 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. additionsaline was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. washeluted with ethyl acetate-methanol-triethylamine (50:5:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was crystallized from ethyl acetate
  10. washwashed with diethyl ether
  11. customrecrystallized in the same manner
  12. customdried

Sources & evidence

ORD record
ord-a0f779fe2b494fb3b125a2c3938e003b
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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