Tert-butyl [2-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate → N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 1874500

Reaktionsgleichung

Reaktionsgleichung von HRID 1874500
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([N:15]=[C:16]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:17]=3)[CH:14]=2)=[CH:4][C:3]=1[NH:24]C(=O)OC(C)(C)C>FC(F)(F)C(O)=O>[NH2:24][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[Cl:1])[O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([N:15]=[C:16]([NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[N:17]=2)[CH:14]=1

Komponenten

3

Edukt 1

HCID 57749186Tert-butyl [2-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate

Produkt 1

HCID 57749285N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (30 mL) was added to tert-butyl [2-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate (5.59 g, 12.6 mmol), and the mixture was stirred at room temperature for 30 min. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with saturated 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-hexane to give the title compound (3.58 g, 83%) as a white solid.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. washthe residue was washed with ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e03c6ae2a60e4eddbca633328483f3be
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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