Ethanol → N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874392

Reaktionsgleichung

[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:18]=[CH:19][C:20]4[N:21]([CH:23]=[C:24]([NH:26]C(=O)C(F)(F)F)[N:25]=4)[CH:22]=3)[CH:11]=2)=[O:8])=[CH:5][C:4]([CH3:33])=[N:3]1.[OH-].[Na+].C(O)C>O>[NH2:26][C:24]1[N:25]=[C:20]2[CH:19]=[CH:18][C:17]([O:16][C:12]3[CH:11]=[C:10]([NH:9][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:33])[CH:5]=4)=[O:8])[CH:15]=[CH:14][CH:13]=3)=[CH:22][N:21]2[CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A mixture of 1,3-dimethyl-N-[3-({2-[(trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1H-pyrazole-5-carboxamide (328 mg, 0.715 mmol), 1N aqueous sodium hydroxide solution (3 mL) and ethanol (3 mL) was stirred at 40° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, methanol/ethyl acetate=0/100→20/80) to give the title compound (205 mg, 79%) as a white solid.

Aufarbeitung

extractionextracted with ethyl acetate (×3)
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by column chromatography (silica gel, methanol/ethyl acetate=0/100→20/80)

Quellen und Nachweise

ORD-Eintrag: ord-e8d24731029c4ab69d016190cc4b6390
Quelldatensatz: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08304557B2

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