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

HRID 1874410Notes

Reaction equation

HRID 1874410 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:29]=[CH:30][CH:31]=2)[O:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([NH:23]C(=O)OCC)=S)=[N:18][CH:19]=2)=[O:8])=[CH:5][C:4]([CH3:32])=[N:3]1.[Cl-].O[NH3+].C([N:39](CC)C(C)C)(C)C.C(O)C>O.CO>[NH2:23][C:21]1[N:20]=[C:17]2[CH:16]=[CH:15][C:14]([O:13][C:12]3[CH:11]=[C:10]([NH:9][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:32])[CH:5]=4)=[O:8])[CH:31]=[CH:30][CH:29]=3)=[CH:19][N:18]2[N:39]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 21645Hydroxylamine HClHCID 81531DiisopropylethylamineHCID 57749218ethyl ({[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate

Product 1

HCID 57749195N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl ({[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate (238 mg, 0.524 mmol), hydroxylammonium chloride (364 mg, 5.24 mmol), N,N-diisopropylethylamine (548 μL, 3.14 mmol), ethanol (3 mL) and methanol (3 mL) was stirred at 60° C. for 5 hr and at 80° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and 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, hexane/ethyl acetate/methanol=50/50/0→40/100/0→40/90/10) and recrystallized from ethyl acetate-hexane to give the title compound (131 mg, 69%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate/methanol=50/50/0→40/100/0→40/90/10)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4b1c3a9d6e184bd08b554bb8a3b5bef2
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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