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4-Aminobenzoic Acid → 4-[(2-Oxo-6-{3-[(thiophene-2-carbonyl)-amino]-benzoyl}-1,2-dihydro-indol-3-ylidenemethyl)-amino]-benzoic acid

HRID 2352864
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HRID 2352864 반응식
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:28].[NH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1>C1COCC1>[O:28]=[C:4]1[C:3](=[CH:2][NH:29][C:30]2[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=2)[C:11]2[C:6](=[CH:7][C:8]([C:12](=[O:13])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[O:22])[CH:15]=3)=[CH:9][CH:10]=2)[NH:5]1
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참가 물질

4

반응물 2

HCID 9784-Aminobenzoic AcidHCID 178517289N-[3-[3-(hydroxymethylidene)-2-oxo-1H-indole-6-carbonyl]phenyl]thiophene-2-carboxamide

생성물 1

HCID 686984204-[(2-Oxo-6-{3-[(thiophene-2-carbonyl)-amino]-benzoyl}-1,2-dihydro-indol-3-ylidenemethyl)-amino]-benzoic acid수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

A small screw cap test tube was charged with Thiophene-2-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 45, 80 mg, 0.2049 mmol) and THF (2 mL). To the resulting solution was added 4-Amino-benzoic acid (34 mg, 0.248 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. The room temperature reaction mixture was concentrated in vacuo. The solid residue was recrystallized from EtOAc (5 mL) and Hexanes (2 mL) yielding the title compound in 81% yield (0.085 g, 0.1668 mmol).

후처리

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. customThe room temperature reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customThe solid residue was recrystallized from EtOAc (5 mL) and Hexanes (2 mL)

출처 및 근거

ORD 기록
ord-5806bbf28bab4453ad4ca4dfc004a54f
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07749530B2

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