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

HRID 490557노트

반응식

HRID 490557 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 11718576n-(1-Isobutyl-3-oxo-2,3-dihydro-1h-indazol-5-yl)-3-trifluoromethyl-benzenesulfonamide수율 21.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
60 °C

실험 절차

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]+).

후처리

  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)

출처 및 근거

ORD 기록
ord-1ac33710e4ea4fbba2e85f7bace6c2d2
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528158B2

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