Cyclopropanecarbonyl chloride → HCID 57749407, compound

HRID 1874458Notes

Reaction equation

HRID 1874458 reaction equation
[NH2:1][C:2]1[N:26]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([CH3:25])=[C:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:16]=3)=[CH:9][N:4]2[N:3]=1.[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1>CN(C)C(=O)C.C(=O)([O-])O.[Na+]>[CH:27]1([C:30]([NH:1][C:2]2[N:26]=[C:5]3[CH:6]=[CH:7][C:8]([O:10][C:11]4[CH:12]=[CH:13][C:14]([CH3:25])=[C:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH:16]=4)=[CH:9][N:4]3[N:3]=2)=[O:31])[CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 57749251HCID 57749251, compound

Product 1

HCID 57749407HCID 57749407, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl {5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-methylphenyl}carbamate (3.52 g, 8.92 mmol) in N,N-dimethylacetamide (30 mL) was added cyclopropanecarbonyl chloride (0.811 mL, 8.93 mmol) at 0° C., and the mixture was stirred at room temperature for 84 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer 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 purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→425/75) to give the title compound (3.87 g, 97%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated 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 column chromatography (silica gel, hexane/ethyl acetate=100/0→425/75)

Sources & evidence

ORD record
ord-70bf5d9694eb4735b5719ac57aa4d7e2
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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