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Ethyl bromoacetate → Ethyl[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]acetate formic acid

HRID 2059926
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2059926
[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][C:30]([O:32][CH2:33][CH3:34])=[O:31].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:30]([OH:32])=[O:31].[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:22]1[CH2:21][CH2:20][C:19]2[C:24](=[CH:25][CH:26]=[CH:27][C:18]=2[C:15]2[N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[C:6]([C:7]#[N:8])[CH:9]=3)[O:17][N:16]=2)[CH2:23]1)[CH3:34]
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Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 441248992-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile

Produkt 1

HCID 131729974Ethyl[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]acetate formic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

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 bromoacetate (35.5 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. The suspension was added to an SCX cartridge, and the product eluted with methanolic ammonia. Concentration in vacuo gave a crude product (43 mg) that was purified by MDAP to give the title compound as a clear film (11.6 mg, 32%). 1H NMR (400 MHz, CDCl3) δ 8.41 (1H, d), 8.33 (1H, dd), 8.09 (1H, br. s), 8.01 (1H, d), 7.34 (1H, apparent t), 7.21 (1H, d), 7.12 (1H, d), 4.80 (1H, sept), 4.24 (2H, q), 4.00 (2H, s), 3.52 (2H, s), 3.35 (2H, t), 3.07 (2H, t), 1.48 (6H, d), 1.31 (3H, t); m/z (ES) 447 [M+H]+.

Aufarbeitung

  1. customirradiated to 60° C. for 5 min in the microwave
  2. additionThe suspension was added to an SCX cartridge
  3. washthe product eluted with methanolic ammonia
  4. concentrationConcentration in vacuo
  5. customgave a crude product (43 mg) that
  6. customwas purified by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-f5646bcb51044bdd9cbbbd4be5649cc0
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08278324B2

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