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 1663925

Reaction equation

HRID 1663925 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-6de9ebcd8fff4d9281da175000bb19f1
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Linked notes

Loading…