Hydrochloric Acid → N-{5-[(2-{[(1-hydroxycyclopropyl)carbonyl]amino}imidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 2391422

Reaction equation

HRID 2391422 reaction equation
C([O:4][C:5]1([C:8]([NH:10][C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([NH:27][C:28]([C:30]5[N:34]([CH3:35])[N:33]=[C:32]([CH3:36])[CH:31]=5)=[O:29])[CH:21]=4)=[N:15][N:14]3[CH:37]=2)=[O:9])[CH2:7][CH2:6]1)(=O)C.[OH-].[Na+].Cl.C(OCC)(=O)C>O1CCCC1>[OH:4][C:5]1([C:8]([NH:10][C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([NH:27][C:28]([C:30]5[N:34]([CH3:35])[N:33]=[C:32]([CH3:36])[CH:31]=5)=[O:29])[CH:21]=4)=[N:15][N:14]3[CH:37]=2)=[O:9])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 575056601-({[6-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]amino}carbonyl)cyclopropyl acetate

Product 1

HCID 57505661N-{5-[(2-{[(1-hydroxycyclopropyl)carbonyl]amino}imidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-({[6-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]amino}carbonyl)cyclopropyl acetate (130 mg, 0.25 mmol) in tetrahydrofuran (2 mL) was added 1N aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 2 hr. 1N Hydrochloric acid (2.5 mL) and ethyl acetate were added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate (×3). Combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate/hexane to give the title compound (99 mg, 86%) as a pale-yellow solid.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (×3)
  2. washCombined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe residue was washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-93bcb31157324996b5848f90983f208e
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Linked notes

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