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

HRID 2059939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059939
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:34])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH2:30][NH:29][CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17].N12CCCN=C1CCCCC2.[C:46]([O:50][CH2:51][CH3:52])(=[O:49])[CH:47]=[CH2:48]>C(#N)C>[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:34])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH2:30][N:29]([CH2:48][CH2:47][C:46]([O:50][CH2:51][CH3:52])=[O:49])[CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 8821Ethyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 684983726-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydroisoquinoline trifluoroacetate

Produkt 1

HCID 59370484Ethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoateAusbeute 103,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydroisoquinoline trifluoroacetate (Example 10; 90 mg; 0.18 mmol) in acetonitrile (3 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 0.16 ml; 1.09 mmol). Ethyl acrylate (0.03 ml; 0.27 mmol) was added to the solution and the resulting mixture stirred at 70° C. for 0.5 h. The mixture was cooled to room temperature and the solvent removed. The residue was partitioned between ethyl acetate and brine, and the aqueous layer further extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (90 mg).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent removed
  3. customThe residue was partitioned between ethyl acetate and brine
  4. extractionthe aqueous layer further extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f96b86cdc35c4c3ea25168d6795eb8ac
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278324B2

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