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

HRID 1874355

Reaction equation

HRID 1874355 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 57749397N-(6-hydroxy[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamideYield 172.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

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 with stirring under ice-cooling cyclopropanecarbonyl chloride (1.15 mL, 12.7 mmol), 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 filtrated. 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.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer 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. filtrationthe residue was collected by filtration
  8. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-b8508a501972407db7c46d734eb00095
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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