Potassium Iodide → HCID 22989260, compound

HRID 1169080Notes

Reaction equation

HRID 1169080 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:14]=2)[N:11]=1.[C:23]1([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:36]1([CH:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:30]2[CH2:31][CH2:32][N:33]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]3[CH:7]=[CH:8][C:9]4[N:10]([CH:12]=[C:13]([C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:14]=4)[N:11]=3)[CH2:34][CH2:35]2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 11110114HCID 11110114, compound

Product 1

HCID 22989260HCID 22989260, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

921 mg of ethyl 2-[6-(4-chlorobutyl)imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate was dissolved in 10 ml of N,N-dimethylformamide; 789 mg of 1-(diphenylmethyl)piperazine, 433 mg of potassium iodide and 520 mg of potassium carbonate were added, followed by stirring at 60° C. for 5 hours. After cooling, ethyl acetate was added; the mixture 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:triethylamine (50:1). The desired fraction was collected, concentrated under reduced pressure and crystallized from ethyl ether-hexane (1:1), collected by filtration, washed with hexane and dried to yield 554 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate:triethylamine (50:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated under reduced pressure
  8. customcrystallized from ethyl ether-hexane (1:1)
  9. filtrationcollected by filtration
  10. washwashed with hexane
  11. customdried

Sources & evidence

ORD record
ord-a1a42d82888540debbc3e261661090fc
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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