Cyclopropanecarbonyl chloride → HCID 25123227, compound

HRID 1874424Notes

Reaction equation

HRID 1874424 reaction equation
[NH2:1][C:2]1[N:28]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([F:27])=[C:15]([NH:17][C:18]([C:20]4[N:24]([CH3:25])[N:23]=[C:22]([CH3:26])[CH:21]=4)=[O:19])[CH:16]=3)=[CH:9][N:4]2[N:3]=1.[CH:29]1([C:32](Cl)=[O:33])[CH2:31][CH2:30]1>CN(C)C(=O)C.C(=O)([O-])O.[Na+]>[CH:29]1([C:32]([NH:1][C:2]2[N:28]=[C:5]3[CH:6]=[CH:7][C:8]([O:10][C:11]4[CH:12]=[CH:13][C:14]([F:27])=[C:15]([NH:17][C:18]([C:20]5[N:24]([CH3:25])[N:23]=[C:22]([CH3:26])[CH:21]=5)=[O:19])[CH:16]=4)=[CH:9][N:4]3[N:3]=2)=[O:33])[CH2:31][CH2:30]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride2×HCID 57749095HCID 57749095, compound

Product 1

HCID 25123227HCID 25123227, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-{5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-fluorophenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (581 mg, 1.52 mmol) in N,N-dimethylacetamide (5 mL) was added with stirring under ice-cooling cyclopropanecarbonyl chloride (166 μL, 1.83 mmol), and the mixture was stirred at room temperature for 1 hr. Cyclopropanecarbonyl chloride (492 μL, 0.966 mmol) was further added and the mixture was stirred for 15 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, 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 purified by column chromatography (silica gel, ethyl acetate) and recrystallized from ethyl acetate to give the title compound (485 mg, 71%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. stirringthe mixture was stirred for 15 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. filtrationfiltrated
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by column chromatography (silica gel, ethyl acetate)
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9e80e0507c2d429d9d9ed8caa1957f74
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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