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Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate → HCID 178452314, 화합물

HRID 1750014
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HRID 1750014 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.[NH:26]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[C:28]([CH:35]=O)=[N:27]1>CO.N1CCCCC1>[NH:26]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[C:28](/[CH:35]=[C:7]2\[O:8][C:4]3[C:3]([CH2:12][N:13]4[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]4)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=3[C:6]\2=[O:9])=[N:27]1
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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 178520050HCID 178520050, 화합물

생성물 1

HCID 178452314HCID 178452314, 화합물수율 64%

시약·촉매·용매 2

HCID 8082Piperidine촉매HCID 887Methanol용매

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온도
60 °C

실험 절차

A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.0366 g, 0.105 mmol) synthesized in Example B1, Step 1 in methanol (2 mL) was added with 1H-pyrazolo[3,4-b]pyridine-3-carboxaldehyde (International Patent Publication WO2010/051561, 0.0162 g, 0.110 mmol) and piperidine (5 drops), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain tert-butyl (Z)-4-({2-[(1H-pyrazolo[3,4-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0321 g, 64%).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-43a0617e72c04848836e651e2443ac7a
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156827B2

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