4-Chlorobenzenesulfonyl chloride → 1,5-bis-(4-chloro-benzenesulfonyl)-6-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

HRID 15724

Reaktionsgleichung

Reaktionsgleichung von HRID 15724
C(OC([N:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][C:11]2[NH:20][N:21]=[CH:22][C:10]=2[CH2:9]1)=O)(C)(C)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(OCC)(=O)C>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:20]2[C:11]3[CH2:12][CH:13]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:8]([S:30]([C:27]4[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=4)(=[O:32])=[O:31])[CH2:9][C:10]=3[CH:22]=[N:21]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Komponenten

4

Edukt 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 593424006-Phenyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

Produkt 1

HCID 593423461,5-bis-(4-chloro-benzenesulfonyl)-6-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Compound 52 from the previous step (1.1 g, 3.67 mmol) was dissolved in ethyl acetate (15 ml). HCl (g) was bubbled into the solution for 5 minutes. Solvent was removed under reduced pressure and the residue was re-dissolved in pyridine (15 ml). 4-chlorophenylsulfonyl chloride (1.55 g, 2.2 eq.) was added to the solution at zero degrees. The mixture was stirred at zero degrees and slowly raised to room temperature upon stirring overnight. Ethyl acetate (100 ml) was added to the reaction mixture, and the solution was washed with sat. NaHCO3 (2×25 ml), 10% HCl solution (2×25 ml) and brine (10 ml). Sample dried over (MgSO4), and solvent was removed under reduced pressure. The crude product was purified via flash chromatography, eluted with EtOAc/hexane (15:85) to give a white solid as the mixture of two regioisomers. LCMS 569.9 (M+23)

Aufarbeitung

  1. customHCl (g) was bubbled into the solution for 5 minutes
  2. customSolvent was removed under reduced pressure
  3. dissolutionthe residue was re-dissolved in pyridine (15 ml)
  4. stirringupon stirring overnight
  5. washthe solution was washed with sat. NaHCO3 (2×25 ml), 10% HCl solution (2×25 ml) and brine (10 ml)
  6. dry with materialSample dried over (MgSO4), and solvent
  7. customwas removed under reduced pressure
  8. customThe crude product was purified via flash chromatography
  9. washeluted with EtOAc/hexane (15:85)
  10. customto give a white solid
  11. additionas the mixture of two regioisomers

Quellen und Nachweise

ORD-Eintrag
ord-f296dfa423414303b11e9b4c72dcf515
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732609B2

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