Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate → tert-butyl (Z)-4-[(6-hydroxy-2-{[5-(2-morpholinoethoxy)-1H-indol-3-yl]methylene}-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate

HRID 1749737노트

반응식

HRID 1749737 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.[O:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][O:34][C:35]2[CH:36]=[C:37]3[C:41](=[CH:42][CH:43]=2)[NH:40][CH:39]=[C:38]3[CH:44]=O)[CH2:28][CH2:27]1>CO.N1CCCCC1>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])/[C:7](=[CH:44]/[C:38]3[C:37]4[C:41](=[CH:42][CH:43]=[C:35]([O:34][CH2:33][CH2:32][N:29]5[CH2:30][CH2:31][O:26][CH2:27][CH2:28]5)[CH:36]=4)[NH:40][CH:39]=3)/[O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]1

참가 물질

5

반응물 2

HCID 60155786Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylateHCID 866819325-(2-morpholinoethoxy)-1H-indole-3-carboxaldehyde

생성물 1

HCID 86681933tert-butyl (Z)-4-[(6-hydroxy-2-{[5-(2-morpholinoethoxy)-1H-indol-3-yl]methylene}-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate수율 81%

시약·촉매·용매 2

HCID 8082Piperidine촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.067 g, 0.19 mmol) obtained in Example A16, Step 1 in methanol (5.0 mL) was added with 5-(2-morpholinoethoxy)-1H-indole-3-carboxaldehyde (0.044 g, 0.16 mmol). Then, the mixture was added with 5 drops of piperidine, and the mixture was stirred at 50° C. for 2 hours. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (95:5)) to obtain tert-butyl (Z)-4-[(6-hydroxy-2-{[5-(2-morpholinoethoxy)-1H-indol-3-yl]methylene}-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.076 g, 81%).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (95:5))

출처 및 근거

ORD 기록
ord-1974cb75ab9c4d24aecf5765cd6f0ecd
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156827B2

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