Potassium Carbonate → HCID 57505520, compound

HRID 2391260Notes

Reaction equation

HRID 2391260 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].I[C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH:22]=[C:23]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[N:24]=2)[N:21]=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][CH:7]=1)[O:8][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH:22]=[C:23]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[N:24]=2)[N:21]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 23665647Potassium tert-butoxideHCID 57441029HCID 57441029, compound

Product 1

HCID 57505520HCID 57505520, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-aminophenol (331 mg, 3.0 mol) in N,N-dimethylformamide (8.0 mL) was added potassium tert-butoxide (355 mg, 3.16 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)propaneamide (0.80 g, 2.53 mmol) and potassium carbonate (175 mg, 1.27 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 magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) and precipitated from hexane/ethyl acetate to give the title compound (420 mg, 56%) as a white 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 magnesium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)
  8. customprecipitated from hexane/ethyl acetate

Sources & evidence

ORD record
ord-4c57a85ce190401eb237e77dc59173ab
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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