Water → N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

HRID 2391117Notes

Reaction equation

HRID 2391117 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1.[CH:12]1([C:15](Cl)=[O:16])[CH2:14][CH2:13]1.O>CN(C)C(=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:15]([CH:12]3[CH2:14][CH2:13]3)=[O:16])[N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 574410246-Iodoimidazo[1,2-B]pyridazin-2-amine

Product 1

HCID 57386058N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution (10 mL) of 6-iodoimidazo[1,2-b]pyridazin-2-amine (1.0 g, 3.85 mmol) in N,N-dimethylacetamide was added cyclopropylcarbonyl chloride (0.38 mL, 4.23 mmol), and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate (4/1) to give the title compound (1.01 g, 80%) as a dark brown powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with hexane/ethyl acetate (4/1)

Sources & evidence

ORD record
ord-d9958f09680b4f76b4a38b19d39c5c3b
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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