Potassium Iodide → HCID 22989367, compound

HRID 1067532Notes

Reaction equation

HRID 1067532 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:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:34][CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]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:41]1([CH:33]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:34][CH:35]2[CH2:40][CH2:39][N:38]([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)[CH2:37][CH2:36]2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 30175844-BenzhydryloxypiperidineHCID 22989273HCID 22989273, compound

Product 1

HCID 22989367HCID 22989367, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1.13 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; 943 mg of 4-(diphenylmethoxy)piperidine, 586 mg of potassium iodide and 488 mg of potassium carbonate were added, followed by stirring at 60° C. for 2 hours. Ice water was added; the mixture was saturated with sodium chloride and extracted 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:methanol (10:1). The desired fraction was collected, concentrated under reduced pressure and dried to yield 571 mg of the title compound.

Workup

  1. extractionextracted 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:methanol (10:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-6a67161696c848f1ac6b71f9fe526809
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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