Sodium Iodide → HCID 22989365, compound

HRID 1067499Notes

Reaction equation

HRID 1067499 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

6-(3-Chloropropionamido)[1,2,4]triazolo[1,5-b]pyridazine (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 recrystalized 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 recrystalized from ethanol

Sources & evidence

ORD record
ord-7c06d7d2ca6e498ea437ace924ac44ed
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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