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

HRID 15724

反応式

HRID 15724 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-f296dfa423414303b11e9b4c72dcf515
出典データセット
uspto-grants-2010_06
特許番号
US07732609B2

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