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

HRID 490557ノート

反応式

HRID 490557 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-1ac33710e4ea4fbba2e85f7bace6c2d2
出典データセット
uspto-grants-2009_05
特許番号
US07528158B2

反応ノート

読み込み中…