Cyclopropanecarbonyl chloride → N-(6-hydroxy[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

HRID 2095792

Reaktionsgleichung

Reaktionsgleichung von HRID 2095792
Br.[NH2:2][C:3]1[N:12]=[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][N:5]2[N:4]=1.[CH:13]1([C:16](Cl)=[O:17])[CH2:15][CH2:14]1>CN(C)C(=O)C.O>[OH:11][C:9]1[CH:8]=[CH:7][C:6]2[N:5]([N:4]=[C:3]([NH:2][C:16]([CH:13]3[CH2:15][CH2:14]3)=[O:17])[N:12]=2)[CH:10]=1

Komponenten

5

Edukt 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 468640672-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-ol hydrobromide

Produkt 1

HCID 57749397N-(6-hydroxy[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamideAusbeute 172,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 2-amino[1,2,4]triazolo[1,5-a]pyridin-6-ol hydrobromide (1.50 g, 4.22 mmol) in N,N-dimethylacetamide (5 mL) was added cyclopropanecarbonyl chloride (1.15 mL, 12.7 mmol) with stirring under ice-cooling, and the mixture was stirred at room temperature 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 filtered. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration, and washed with ethyl acetate-hexane to give the title compound (1.59 g, 89%) as a white solid.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. filtrationthe residue was collected by filtration
  9. washwashed with ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-4c58286230504e27b34ed0e9143de793
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445509B2

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