Ethanol → N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

HRID 1874530

Reaktionsgleichung

C(OC(=O)[NH:5][C:6](=S)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=3)=[O:23])[CH:16]=2)=[CH:10][N:9]=1)C.[Cl-].O[NH3+].C([N:39](CC)C(C)C)(C)C.C(O)C>CO>[NH2:39][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:16]=[C:17]([NH:21][C:22]([C:24]4[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=4)=[O:23])[CH:18]=[CH:19][CH:20]=3)=[CH:10][N:9]2[N:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of ethyl{[5-(3-{[(3-methylpyridin-2-yl)carbonyl]amino}phenoxy)pyridin-2-yl]carbamothioyl}carbamate (2.00 g, 4.43 mmol), hydroxylammonium chloride (3.13 g, 45.0 mmol), N,N-diisopropylethylamine (4.70 mL, 26.9 mmol), ethanol (50 mL) and methanol (50 mL) was stirred at 80° C. for 5 hr. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate to give the title compound (1.35 g, 84%) as a white solid.

Aufarbeitung

concentrationThe reaction solution was concentrated under reduced pressure, and ethyl acetate
additionwas added to the residue
washThe mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
concentrationThe filtrate was concentrated under reduced pressure
washthe residue was washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-8e6cc0b681c94bcfb529bf2a39f59fa8
Quelldatensatz: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08304557B2

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