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

HRID 9210

Reaktionsgleichung

Reaktionsgleichung von HRID 9210
[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]([S:26][CH3:27])[C:17]([NH:18][C:19](=O)OC(C)(C)C)=[C:13]2[CH:12]=[CH:11][CH:10]=1.[H-].[Na+].I[CH2:31][CH2:32]C.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]([S:26][CH3:27])[C:17]([NH:18][CH2:19][CH2:31][CH3:32])=[C:13]2[CH:12]=[CH:11][CH:10]=1

Komponenten

9

Edukt 5

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 21866389Hydrogen chloride-ethyl acetateHCID 21984611tert-butyl N-[7-(2,4-dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate

Produkt 1

HCID 21984560N-[7-(2,4-Dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N-propylamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

After dissolving tert-butyl N-[7-(2,4-dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate (150 mg) in N,N-dimethylformamide (3 mL), sodium hydride (60%, 21 mg) was added while cooling on ice, and then 1-iodopropane (0.041 mL) was added and the mixture was stirred for 30 minutes. 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 distilled off 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 (4 mL) was added, and the mixture was stirred at room temperature for 2 hours. 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 (60 mg) was obtained from the n-hexane:ethyl acetate (20:1) fraction as a yellow oil.

Aufarbeitung

  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. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product
  8. stirringthe mixture was stirred at room temperature for 2 hours
  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

Quellen und Nachweise

ORD-Eintrag
ord-d6d9ef502a3f4df18fbb4eeb81fb5ea4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091215B2

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