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

HRID 1874443

Reaktionsgleichung

Reaktionsgleichung von HRID 1874443
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:29]=[C:30]([CH3:32])[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]([CH3:33])=[N:3]1.[Cl-].O[NH3+].C([N:40](CC)C(C)C)(C)C.C(O)C>CO>[NH2:40][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]([CH3:33])[CH:5]=4)=[O:8])[CH:31]=[C:30]([CH3:32])[CH:29]=3)=[CH:19][N:18]2[N:23]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 21645Hydroxylamine HClHCID 81531DiisopropylethylamineHCID 57749265ethyl ({[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-5-methylphenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate

Produkt 1

HCID 57749338N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl ({[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-5-methylphenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate (2.65 g, 4.76 mmol), hydroxylammonium chloride (2.96 g, 42.5 mmol), N,N-diisopropylethylamine (5.00 mL, 28.7 mmol), ethanol (100 mL) and methanol (100 mL) was stirred at 80° C. for 14 hr. The reaction solution was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure and washed with ethanol-ethyl acetate to give the title compound (1.29 g, 72%) as a white solid.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. washwashed with ethanol-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9b146da2cae44db68fc3da78c529a048
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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