Reaktionsgleichung
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=O)=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][CH2:17][O:18]C1CCCCO1)[CH3:2].[F:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=S)[CH:29]=[CH:30][CH:31]=1.C[Si](C)(C)[Si](C)(C)C.[Li].[NH2:44][NH2:45].C(O)(=O)C>C(OCC)(=O)C.C1COCC1>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C:9]3[C:10]2=[N:44][NH:45][C:33]=3[NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=2)=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][CH2:17][OH:18])[CH3:2]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a mixture of 6-Ethoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one (Intermediate AA) (0.100 g, 0.0003 mol), 3-fluorophenyl isothiocyanate (Compound 4a) (0.043 mL, 0.00036 mol) and THF (3 mL) was added lithium hexamethyldisilane (0.360 mL, 0.00036 mol) dropwise at room temperature with stirring. The reaction mixture was stirred for 48 h. Hydrazine (0.011 mL, 0.00036 mol) and acetic acid (0.021 mL, 0.00036 mol) was added to the reaction mixture, which was then heated at reflux temperature for 12 h. The reaction solution was then diluted with ethyl acetate, washed with water and dried over MgSO4. The solvent was removed in vacuo and the crude material was purified on the reverse phase HPLC and converted to the desired product upon standing in the 0.1% TFA solution. Lyophilization yielded the title compound as a white powder. MS m/z 384.2 (M+H)+;
Aufarbeitung
- stirringThe reaction mixture was stirred for 48 h
- temperaturewas then heated
- temperatureat reflux temperature for 12 h
- washwashed with water
- dry with materialdried over MgSO4
- customThe solvent was removed in vacuo
- customthe crude material was purified on the reverse phase HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-fc8a575e0cc74445b882d49375af1e7d
- Quelldatensatz
- uspto-grants-2007_03
- Patentnummer
- US07196110B2
Verknüpfte Notizen
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