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Trifluoroacetic acid → 6-(2-(piperazin-1-yl)ethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331294
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HRID 331294 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:9]=2)[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:3]1[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[N:14]1([CH2:13][CH2:12][O:11][C:8]2[CH:9]=[C:10]3[C:5]([C:4]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[C:3]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)[C:2]3=[O:1])=[CH:6][CH:7]=2)[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 70312805tert-butyl 4-(2-(1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yloxy)ethyl)piperazine-1-carboxylate

생성물 1

HCID 510018316-(2-(piperazin-1-yl)ethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

실험 절차

To a solution of tert-butyl 4-(2-(1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yloxy)ethyl)piperazine-1-carboxylate (0.38 mmol, 200 mg) obtained in Step 2 of Example 44 in CH2Cl2 (0.3M) was added TFA (20 eq). The resulting mixture was stirred at room temperature for 40 min and diluted with CH2Cl2. The solution was basicified to pH 9 by the addition of 3N NaOH. The mixture was washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (acetone/hexanes=1:1) to obtain the title compound (75%).

후처리

  1. washThe mixture was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (acetone/hexanes=1:1)

출처 및 근거

ORD 기록
ord-d1edc047765948a3941283abebe1d577
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877747B2

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