N-(3-Aminophenyl)methanesulfamide → tert-butyl 2-(2-((3-(methylsulfonamido) phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate

HRID 1038423

반응식

HRID 1038423 반응식
Cl[C:2]1[O:3][C:4]([C:7]2[N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:5][N:6]=1.[NH2:23][C:24]1[CH:25]=[C:26]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=1>CC(O)C>[CH3:34][S:31]([NH:30][C:26]1[CH:25]=[C:24]([NH:23][C:2]2[O:3][C:4]([C:7]3[N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]4[C:14]([CH:15]=3)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:5][N:6]=2)[CH:29]=[CH:28][CH:27]=1)(=[O:33])=[O:32]

참가 물질

4

반응물 2

HCID 2734262N-(3-Aminophenyl)methanesulfamideHCID 71060197tert-butyl 2-(2-chlorooxazol-5-yl)-1H-indole-1-carboxylate

생성물 1

HCID 71060239tert-butyl 2-(2-((3-(methylsulfonamido) phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate수율 54%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of tert-butyl 2-(2-chlorooxazol-5-yl)-1H-indole-1-carboxylate 21 (0.281 g, 0.883 mmol) and commercially available N-(3-aminophenyl)methanesulfonamide 6 (0.321 g, 1.723 mmol) in 2-propanol (20 mL) was heated to 80° C. for 14 h with stirring. Upon cooling, solvent was evaporated and silica column purified (Biotage) (Acetone/hexane as an eluent) to provide tert-butyl 2-(2-((3-(methylsulfonamido) phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate 24 (0.221 g, 54% yield) as solid. MS (ES) m/z 469 (M+H+).

후처리

  1. temperatureUpon cooling
  2. customsolvent was evaporated
  3. customsilica column purified (Biotage) (Acetone/hexane as an eluent)

출처 및 근거

ORD 기록
ord-b5c68f57f3b344ec80baa632b7eac6ce
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551992B2

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