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

Reaktionsgleichung

Reaktionsgleichung von HRID 2391422
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

Komponenten

6

Edukt 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

Produkt 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-carboxamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-93bcb31157324996b5848f90983f208e
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273741B2

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