Acetyl chloride → N-(3-{[2-(acetylamino)[1,2,4]triazolo[1,5-a]pyridin-6-yl]oxy}phenyl)-3-methylpyridine-2-carboxamide

HRID 1874532Notes

Reaction equation

HRID 1874532 reaction equation
[NH2:1][C:2]1[N:27]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18]([C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:4]2[N:3]=1.[C:28](Cl)(=[O:30])[CH3:29]>CN(C)C(=O)C.C(=O)([O-])O.[Na+]>[C:28]([NH:1][C:2]1[N:27]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18]([C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:4]2[N:3]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 57749272N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

Product 1

HCID 57749088N-(3-{[2-(acetylamino)[1,2,4]triazolo[1,5-a]pyridin-6-yl]oxy}phenyl)-3-methylpyridine-2-carboxamideYield 66.5%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (120 mg, 0.333 mmol) in N,N-dimethylacetamide (5 mL) was added acetyl chloride (24.0 μL, 0.338 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with 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 purified by silica gel column chromatography (0%→100% ethyl acetate-hexane) to give the title compound (89.1 mg, 66%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution 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 silica gel column chromatography (0%→100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-8336819b943a4bfb81865c23f2b0e850
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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