6-(3-Methoxyphenyl)-1,3-dihydroindol-2-one → 4-(2-Carboxyethyl)-5-[6-(3-methoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid

HRID 24550

반응식

HRID 24550 반응식
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=O)=[C:9]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[C:10]=1[CH3:11])=[O:5])C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([C:29]2[CH:37]=[C:36]3[C:32]([CH2:33][C:34](=[O:38])[NH:35]3)=[CH:31][CH:30]=2)[CH:26]=[CH:27][CH:28]=1>N1CCCCC1.C(O)C>[C:14]([CH2:13][CH2:12][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:3])=[O:5])[NH:7][C:8]=1[CH:19]=[C:33]1[C:32]2[C:36](=[CH:37][C:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=3)=[CH:30][CH:31]=2)[NH:35][C:34]1=[O:38])([OH:16])=[O:15]

참가 물질

5

반응 조건

온도
90 °C

실험 절차

5-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (281 mg), 6-(3-methoxy-phenyl)-2-oxindole (287 mg), and piperidine (2 drops) in ethanol (5 mL) were stirred at 90° C. overnight. The precipitate was filtered and washed with ethanol. The yellow orange solid and potassium hydroxide (4 pellets) were stirred in ethanol (3 mL) at 90° C. for 2.5 hours. The reaction mixture was cooled and concentrated. The residue was dissolved into water and acidified with 2 N hydrochloric acid to pH 2. The precipitate was filtered, washed with water, and dried in a vacuum oven overnight to give 413 mg of 4-(2-Carboxyethyl)-5-[6-(3-methoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid

후처리

  1. filtrationThe precipitate was filtered
  2. washwashed with ethanol
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved into water
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customdried in a vacuum oven overnight

출처 및 근거

ORD 기록
ord-a4195a0932a748d4ba0033ecb630ebd4
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855730B2

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