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Ethyl Acrylate → Ethyl 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate

HRID 2059943
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2059943
FC(F)(F)C(O)=O.[CH3:8][CH:9]([O:11][C:12]1[CH:19]=[CH:18][C:17]([C:20]2[O:24][N:23]=[C:22]([C:25]3[C:26]([CH3:35])=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH2:31][NH:30][CH2:29][CH2:28]4)[N:21]=2)=[CH:16][C:13]=1[C:14]#[N:15])[CH3:10].[C:36]([O:40][CH2:41][CH3:42])(=[O:39])[CH:37]=[CH2:38].N12CCCN=C1CCCCC2>C(#N)C>[C:14]([C:13]1[CH:16]=[C:17]([C:20]2[O:24][N:23]=[C:22]([C:25]3[C:26]([CH3:35])=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH2:31][N:30]([CH2:38][CH2:37][C:36]([O:40][CH2:41][CH3:42])=[O:39])[CH2:29][CH2:28]4)[N:21]=2)[CH:18]=[CH:19][C:12]=1[O:11][CH:9]([CH3:8])[CH3:10])#[N:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8821Ethyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 575058522-[(1-Methylethyl)oxy]-5-[3-(5-methyl-1,2,3,4-tetrahydro-6-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile trifluoroacetate

Produkt 1

HCID 57505851Ethyl 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoateAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-[(1-methylethyl)oxy]-5-[3-(5-methyl-1,2,3,4-tetrahydro-6-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile trifluoroacetic acid salt (Example 11; 100 mg, 0.20 mmol), ethyl acrylate (31 mg, 33 μl, 0.31 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 187 mg, 185 μl, 1.23 mmol) in acetonitrile (3 ml) was stirred at room temperature for 3 hours. The solvent was evaporated and the residue dissolved in ethyl acetate (10 ml); the solution was washed with water (5 ml), dried and evaporated. Purification of the residue by chromatography on silica gel, eluting with 10% ethyl acetate in cyclohexane gave the title compound as a colourless oil (86 mg).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (10 ml)
  3. washthe solution was washed with water (5 ml)
  4. customdried
  5. customevaporated
  6. customPurification of the residue by chromatography on silica gel
  7. washeluting with 10% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-59232db235b44a3c9fc00d66010d15b9
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08278324B2

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