Potassium Iodide → HCID 22989334, compound

HRID 1067539Notes

Reaction equation

HRID 1067539 reaction equation
CS(O[CH2:6][CH2:7][NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH:15]=[C:16]([C:18]([CH3:26])([CH3:25])[C:19]([O:21]C(C)C)=[O:20])[N:17]=2)[N:14]=1)(=O)=O.[C:27]1([CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CN(C)C=O>[C:40]1([CH:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:34]2[CH2:35][CH2:36][N:37]([CH2:6][CH2:7][NH:8][C:9]3[CH:10]=[CH:11][C:12]4[N:13]([CH:15]=[C:16]([C:18]([CH3:25])([CH3:26])[C:19]([OH:21])=[O:20])[N:17]=4)[N:14]=3)[CH2:38][CH2:39]2)[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 22989273HCID 22989273, compound

Product 1

HCID 22989334HCID 22989334, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1.24 g of isopropyl 2-[6-[2-(methanesulfonyloxy)ethylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate was dissolved in 15 ml of N,N-dimethylformamide; 977 mg of 1-(diphenylmethyl)piperazine, 642 mg of potassium iodide and 535 mg of potassium carbonate were added, followed by stirring at room temperature for 1 hour and at 60° C. for 1.5 hours. Ice water and sodium chloride were added, followed by extraction with ethyl acetate; the extract was washed with saturated saline and dried with magnesium sulfate. The dry product was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography and eluted with ethyl acetate. The desired fraction was collected, concentrated under reduced pressure and dried to yield 570 mg of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe extract was washed with saturated saline
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe dry product was concentrated under reduced pressure
  5. washeluted with ethyl acetate
  6. customThe desired fraction was collected
  7. concentrationconcentrated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-f700dc13ff284fceb99a55ac31d223b4
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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