Potassium Carbonate → N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamide

HRID 2391338Notes

Reaction equation

HRID 2391338 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].CC(C)([O-])C.[K+].I[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([CH:23]=[C:24]([NH:26][C:27](=[O:29])[CH3:28])[N:25]=2)[N:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH3:8])[O:9][C:17]1[CH:18]=[CH:19][C:20]2[N:21]([CH:23]=[C:24]([NH:26][C:27](=[O:29])[CH3:28])[N:25]=2)[N:22]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 178203-Amino-p-cresolHCID 23665647Potassium tert-butoxideHCID 57441059N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide

Product 1

HCID 57505579N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamideYield 42.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-amino-4-methylphenol (1.22 g, 9.93 mmol) in N,N-dimethylformamide (25.0 mL) was added potassium tert-butoxide (1.16 g, 10.3 mmol), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture were added N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (2.5 g, 8.28 mmol) and potassium carbonate (0.57 g, 4.14 mmol), and the mixture was stirred at 140° C. for 16 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran, washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate alone) and the obtained residue was washed with hexane/ethyl acetate, and filtrated to give the title compound (1.04 g, 42%) as a brown powder.

Workup

  1. stirringthe mixture was stirred at 140° C. for 16 hr
  2. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate alone) and the obtained residue
  8. washwas washed with hexane/ethyl acetate
  9. filtrationfiltrated

Sources & evidence

ORD record
ord-7dc727de64344175be7fd66ebe9b921e
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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