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Hydrochloric Acid → methyl (Z)-3-{[6-hydroxy-3-oxo-7-(piperazin-1-ylmethyl)benzofuran-2(3H)-ylidene]methyl}-1H-indole-6-carboxylate

HRID 1749747
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인쇄 미리보기

반응식

HRID 1749747 반응식
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[C:23]3[O:22]/[C:21](=[CH:24]\[C:25]4[C:33]5[C:28](=[CH:29][C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=5)[NH:27][CH:26]=4)/[C:20](=[O:38])[C:19]=3[CH:18]=[CH:17][C:16]=2[OH:39])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[OH:39][C:16]1[CH:17]=[CH:18][C:19]2[C:20](=[O:38])/[C:21](=[CH:24]/[C:25]3[C:33]4[C:28](=[CH:29][C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=4)[NH:27][CH:26]=3)/[O:22][C:23]=2[C:15]=1[CH2:14][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1
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참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 86681942methyl (Z)-3-[(7-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-6-hydroxy-3-oxobenzofuran-2(3H)-ylidene)methyl]-1H-indole-6-carboxylate

생성물 1

HCID 71278517methyl (Z)-3-{[6-hydroxy-3-oxo-7-(piperazin-1-ylmethyl)benzofuran-2(3H)-ylidene]methyl}-1H-indole-6-carboxylate수율 43.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 31275
1,4-Dioxane
용매

실험 절차

A solution of methyl (Z)-3-[(7-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-6-hydroxy-3-oxobenzofuran-2(3H)-ylidene)methyl]-1H-indole-6-carboxylate (0.020 g, 0.037 mmol) in methylene chloride (2.0 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2.0 mL), and then the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, then the residue was added with an excessive amount of triethylamine, and the mixture was azeotroped with toluene. The resulting residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain methyl (Z)-3-{[6-hydroxy-3-oxo-7-(piperazin-1-ylmethyl)benzofuran-2(3H)-ylidene]methyl}-1H-indole-6-carboxylate (0.007 g, 43%).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with an excessive amount of triethylamine
  3. customthe mixture was azeotroped with toluene
  4. washThe resulting residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

출처 및 근거

ORD 기록
ord-6fd01017f2904cd7ab1c72cd445a857e
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156827B2

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