Potassium Carbonate → N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)methanesulfonamide

HRID 1035810

반응식

HRID 1035810 반응식
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[O:14][C:15]([C:18]3[N:19](C(OC(C)(C)C)=O)[C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][N:17]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+]>CO.CC(C)=O.CCCCCC>[NH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[C:18]1[C:15]1[O:14][C:13]([NH:12][C:8]2[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:11]=[CH:10][CH:9]=2)=[N:17][CH:16]=1

참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 71060239tert-butyl 2-(2-((3-(methylsulfonamido) phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate

생성물 1

HCID 71060475N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)methanesulfonamide수율 63.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 21880519Acetone hexane용매

실험 절차

To a stirred solution of tert-butyl 2-(2-((3-(methylsulfonamido) phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate 24 (0.221 g, 0.472 mmol) in methanol (30 mL) was added potassium carbonate (0.652 g, 4.71 mmol) at room temperature. Reaction mixture was refluxed for 2 hours. After completion of the reaction (as judged by TLC) it was concentrated using rotavapour and the crude product was purified by MPLC column chromatography (Biotage; Acetone/hexane as an eluent) to provide N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)methanesulfonamide 25 (0.11 g, 63% yield) as a solid. MS (ES) m/z 369 (M+H+).

후처리

  1. customReaction mixture
  2. temperaturewas refluxed for 2 hours
  3. customAfter completion of the reaction (as judged by TLC) it
  4. concentrationwas concentrated
  5. customthe crude product was purified by MPLC column chromatography (Biotage

출처 및 근거

ORD 기록
ord-a96b654270054dc6aa19581e32a538bc
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546400B2

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