Sodium Hydroxide → N-{3-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}cyclopropanecarboxamide

HRID 1663994Notes

Reaction equation

HRID 1663994 reaction equation
C([NH:4][C:5]1[N:6]=[C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([NH:20][C:21]([CH:23]4[CH2:25][CH2:24]4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[N:9][N:8]2[CH:26]=1)(=O)C.Cl.C(OCC)(=O)C.[OH-].[Na+]>CO>[NH2:4][C:5]1[N:6]=[C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([NH:20][C:21]([CH:23]4[CH2:25][CH2:24]4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[N:9][N:8]2[CH:26]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 57505442N-{3-[(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}cyclopropanecarboxamide

Product 1

HCID 57505725N-{3-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}cyclopropanecarboxamideYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-{3-[(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}cyclopropanecarboxamide (465 mg, 1.32 mmol), 4N hydrochloric acid-ethyl acetate solution (10 mL) and methanol (10 mL) was stirred at room temperature for 14 hr. The reaction mixture was neutralized by the addition of 8N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. 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 ethyl acetate/diisopropyl ether to give the title compound (376 mg, 92%) as a pale-green powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  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 ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-206d9872cd71482cbe88488d1e2f9b65
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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