Sodium Hydroxide → N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)amine

HRID 9200

Reaction equation

HRID 9200 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:26][CH3:27])[C:17]([NH:18]C(=O)OC(C)(C)C)=[C:13]2[CH:12]=[CH:11][CH:10]=1.[H-].[Na+].[CH3:30][O:31][CH2:32][CH2:33]Br.Cl.C(OCC)(=O)C.[OH-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:26][CH3:27])[C:17]([NH:18][CH2:33][CH2:32][O:31][CH3:30])=[C:13]2[CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 21866389Hydrogen chloride-ethyl acetateHCID 21984513tert-butyl N-[7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]carbamate

Product 1

HCID 21984623N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

After dissolving tert-butyl N-[7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]carbamate (57 mg) in N,N-dimethylformamide (2 mL), sodium hydride (60%, 7.3 mg) was added while cooling on ice, and then 2-bromoethyl methyl ether (0.015 mL) was added and the mixture was stirred for 1 hour. Water was added to the reaction mixture, extraction was performed with ethyl acetate and the extract was washed with brine. The obtained organic layer was dried over anhydrous magnesium sulfate and filtered, and then the solvent was concentrated under reduced pressure to obtain a crude product. This was dissolved in ethyl acetate (1 mL) without purification, a 4 N hydrochloric acid/ethyl acetate solution (2 mL) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with 5 N aqueous sodium hydroxide while cooling on ice, and then extraction was performed with ethyl acetate and the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (46 mg) was obtained from the n-hexane:ethyl acetate (5:1) fraction as a yellow oil.

Workup

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. washthe extract was washed with brine
  4. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customto obtain a crude product
  8. stirringthe mixture was stirred at room temperature for 1 hour
  9. temperaturewhile cooling on ice
  10. extractionextraction
  11. washthe organic layer was washed with water and brine
  12. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  13. concentrationthe solvent was concentrated under reduced pressure
  14. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff1ad39d39ca41c0b5fe15c41495f583
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Linked notes

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