3-(Trifluoromethyl)benzenesulfonyl chloride → n-(1-Isobutyl-3-oxo-2,3-dihydro-1h-indazol-5-yl)-3-trifluoromethyl-benzenesulfonamide

HRID 490557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490557
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[NH:6][C:5]2=[O:15].[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>N1C=CC=CC=1>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][S:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:28])[F:29])[CH:19]=3)(=[O:26])=[O:25])=[CH:10][CH:9]=2)[C:5](=[O:15])[NH:6]1)[CH:12]([CH3:13])[CH3:14]

Komponenten

4

Edukt 2

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 688331235-Amino-1-isobutyl-1,2-dihydro-indazol-3-one

Produkt 1

HCID 11718576n-(1-Isobutyl-3-oxo-2,3-dihydro-1h-indazol-5-yl)-3-trifluoromethyl-benzenesulfonamideAusbeute 21,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5-amino-1-isobutyl-1,2-dihydro-indazol-3-one (0.04 g) in pyridine (1 mL) was added 3-trifluoromethylbenzenesulfonylchoride (0.041 g) in one go. The solution was stirred at 60° C. for 24 hours. The pyridine was then removed in vacuo and the residue was dissolved in EtOAc/water and separated. The aqueous phase was extracted a further two times with EtOAc and the combined organic phases were washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the volatiles were removed in vacuo to afford a crude residue. The crude material was purified via flash column chromatography eluting with EtOAc/nHeptane/1% AcOH) to afford the desired N-(1-isobutyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-trifluoromethyl-benzenesulfonamide (0.015 g) as a pale yellow powder. MS (ESI+): 414.4[M+H]+).

Aufarbeitung

  1. customThe pyridine was then removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc/water
  3. customseparated
  4. extractionThe aqueous phase was extracted a further two times with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe drying agent was removed by filtration
  8. customthe volatiles were removed in vacuo
  9. customto afford a crude residue
  10. customThe crude material was purified via flash column chromatography
  11. washeluting with EtOAc/nHeptane/1% AcOH)

Quellen und Nachweise

ORD-Eintrag
ord-1ac33710e4ea4fbba2e85f7bace6c2d2
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528158B2

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