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Sodium Hydroxide → 5-[3-(3,4-Dihydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile

HRID 2383302
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HRID 2383302 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].BrN1C(=O)CCC1=O.[OH-].[Na+]>C(Cl)Cl>[CH:23]1[C:24]2[C:19](=[C:18]([C:15]3[N:14]=[C:13]([C:10]4[CH:11]=[CH:12][C:5]([O:4][CH:2]([CH3:3])[CH3:1])=[C:6]([CH:9]=4)[C:7]#[N:8])[O:17][N:16]=3)[CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:21][N:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 441248992-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile

생성물 1

HCID 595910795-[3-(3,4-Dihydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

A solution of 2-[(1-methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile (Preparation 7, 50 mg, 0.139 mmol) and N-bromosuccinimide (29.6 mg, 0.166 mmol) in DCM (5 mL) was heated at reflux for 3 h, then cooled to room temperature. 2M aqueous NaOH (5 mL) was added, and the layers separated. The aqueous was extracted with DCM (5 mL) and the organic layers combined. Concentration in vacuo gave the title compound as a yellow solid (47.8 mg). 1H NMR (400 MHz, CDCl3) δ 8.52 (1H, t), 8.43 (1H, d), 8.34 (1H, dd), 8.23 (1H, dd), 7.55-7.51 (2H, m), 7.14 (1H, d), 4.81 (1H, sept), 3.86 (2H, td), 3.31 (2H, t), 1.48 (6H, d); m/z (ES) 359 [M+H]+.

후처리

  1. temperatureat reflux for 3 h
  2. customthe layers separated
  3. extractionThe aqueous was extracted with DCM (5 mL)
  4. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-06c8d64399604a5aa07ce0d115f155f8
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263620B2

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