Acetic Acid → HCID 178465801, Verbindung

HRID 1714452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1714452
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][O:17]C1CCCCO1)[C:9](=O)[CH2:8][CH2:7]2)[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:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][OH:17])[C:9]1=[N:44][NH:45][C:33]([NH:32][C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=3)=[C:8]1[CH2:7]2)[CH3:2]

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 9321HydrazineHCID 98343-Fluorophenyl isothiocyanate2×HCID 18445696HCID 18445696, VerbindungHCID 57425481Lithium hexamethyldisilane

Produkt 1

HCID 178465801HCID 178465801, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 5-Ethoxy-6-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one, (Intermediate Z) (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 5 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 384.4 (M+H)+;

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 5 h
  2. temperaturewas then heated
  3. temperatureat reflux temperature for 12 h
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe crude material was purified on the reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-648d87e400614e7b95c427e497434191
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795440B2

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