Sodium Iodide → HCID 22989365, compound

HRID 1169029Notes

Reaction equation

HRID 1169029 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([N:13]=[CH:14][N:15]=2)[N:12]=1)=[O:5].[C:16]1([CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:29]1([CH:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]2[CH2:24][CH2:25][N:26]([CH2:2][CH2:3][C:4]([NH:6][C:7]3[CH:8]=[CH:9][C:10]4[N:11]([N:13]=[CH:14][N:15]=4)[N:12]=3)=[O:5])[CH2:27][CH2:28]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 22989399HCID 22989399, compound

Product 1

HCID 22989365HCID 22989365, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Chloro-N-([1,2,4]triazolo[1,5-b]pyridazin-6-yl)propionamide (339 mg) and 1-(diphenylmethyl)piperazine (379 mg) were dissolved in acetonitrile (15 ml), followed by addition of sodium iodide (447 mg) and potassium carbonate (249 mg). The mixture was stirred at room temperature for 15 hours and refluxed under heating for 8 hours. After the mixture was cooled, ice-water was added thereto, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride saturated solution, dried over magnesium sulfate and concentrated under reduced pressure. The resulting crystals were recrystallized from ethanol to yield the title compound (408 mg).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 8 hours
  3. temperatureAfter the mixture was cooled
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with an aqueous sodium chloride saturated solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-b05af23c47e8429283d8ea45770129f8
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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