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Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate → tert-butyl (Z)-4-({2-[(6-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate

HRID 1749821
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HRID 1749821 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[C:26]([C:28]1[N:33]=[C:32]2[NH:34][CH:35]=[C:36]([CH:37]=O)[C:31]2=[CH:30][CH:29]=1)#[CH:27]>CO.N1CCCCC1>[C:26]([C:28]1[N:33]=[C:32]2[NH:34][CH:35]=[C:36](/[CH:37]=[C:7]3\[O:8][C:4]4[C:3]([CH2:12][N:13]5[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]5)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=4[C:6]\3=[O:9])[C:31]2=[CH:30][CH:29]=1)#[CH:27]
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참가 물질

5

반응물 2

HCID 60155786Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylateHCID 866820046-ethynyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde

생성물 1

HCID 86682005tert-butyl (Z)-4-({2-[(6-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate수율 73.1%

시약·촉매·용매 2

HCID 8082Piperidine촉매
HCID 887
Methanol
용매

실험 절차

A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.017 g, 0.049 mmol) obtained in Example A16, Step 1 in methanol (2.0 mL) was added with 6-ethynyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.007 g, 0.041 mmol). Then, the mixture was added with 5 drops of piperidine, and then the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and then the residue was washed with methylene chloride to obtain tert-butyl (Z)-4-({2-[(6-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.015 g, 60%).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was washed with methylene chloride

출처 및 근거

ORD 기록
ord-1136e4203eb349f2aad78e9cbe260a5b
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156827B2

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