Hydrochloric Acid → 3-({2-[(Cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)benzoic acid

HRID 2391215Notes

Reaction equation

HRID 2391215 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=4)[C:19]([O:21]C)=[O:20])=[N:11][N:10]3[CH:26]=2)=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCCC1>[CH:1]1([C:4]([NH:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=4)[C:19]([OH:21])=[O:20])=[N:11][N:10]3[CH:26]=2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57505482Methyl 3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)benzoate

Product 1

HCID 575054813-({2-[(Cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)benzoic acidYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)benzoate (225 mg, 0.64 mmol) in tetrahydrofuran (5.0 mL) was added 1N sodium hydroxide (2.5 mL), and the mixture was stirred at room temperature for 24 hr. 1N Hydrochloric acid was added to the mixture (pH=3), and the aqueous layer was extracted three times with ethyl acetate/tetrahydrofuran. Combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was filtrated, and washed with ethyl acetate/hexane to give the title compound (150 mg, 69%) as a white powder.

Workup

  1. extractionthe aqueous layer was extracted three times with ethyl acetate/tetrahydrofuran
  2. washCombined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure
  6. filtrationthe residue was filtrated
  7. washwashed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-9a15cd1fd84649ada02ebeb97f576c66
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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