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Cesium carbonate → ethyl 4-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]butanoate formic acid salt

HRID 2059928
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HRID 2059928 반응식
[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][NH:22][CH2:23]4)[N:14]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].Br[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:32]([OH:34])=[O:33].[C:7]([C:6]1[CH:9]=[C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][N:22]([CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:23]4)[N:14]=2)[CH:11]=[CH:12][C:5]=1[O:4][CH:2]([CH3:1])[CH3:3])#[N:8]
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrate2회HCID 441248992-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile

생성물 1

HCID 68500834ethyl 4-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]butanoate formic acid salt

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

A suspension of 2-[(1-methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile (Example 3, 28.8 mg, 0.080 mmol), ethyl 4-bromobutyrate (45.8 μl, 0.32 mmol) and Cs2CO3 (130 mg, 0.40 mmol) in DMF (2 mL) was stirred at room temperature for 1 h, and then irradiated to 60° C. for 5 min in the microwave. More ethyl 4-bromobutyrate (45.8 μl, 0.32 mmol) was added and the suspension was stirred at room temperature for 3.5 h. It was then filtered, concentrated in vacuo and purified by MDAP to give the title compound as a yellow film (8.0 mg, 21%). 1H NMR (400 MHz, CDCl3) δ 8.42 (1H, d), 8.34 (1H, dd), 8.27 (br. s), 8.09 (1H, d), 7.39 (1H, t), 7.27 (1H, d), 7.13 (1H, d), 4.80 (1H, sept), 4.19 (2H, s), 4.13 (2H, q), 3.47 (2H, t), 3.28 (2H, t), 2.99 (2H, t), 2.44 (2H, t), 2.10 (2H, quin), 1.48 (6H, d), 1.25 (3H, t); m/z (ES) 475 [M+H]+.

후처리

  1. customirradiated to 60° C. for 5 min in the microwave
  2. stirringthe suspension was stirred at room temperature for 3.5 h
  3. filtrationIt was then filtered
  4. concentrationconcentrated in vacuo
  5. custompurified by MDAP

출처 및 근거

ORD 기록
ord-165c1bfa5eee4175b170599625078d91
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08278324B2

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