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

HRID 1874530Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-8e6cc0b681c94bcfb529bf2a39f59fa8
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Reaction notes

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