Acetophenone → 4,7,7-trimethyl-4-phenyl-3-(trifluoromethyl)-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-b]quinolin-5(4H)-one

HRID 510022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510022
[CH3:1][C:2]1([CH3:10])[CH2:7][C:6](=O)[CH2:5][C:4](=[O:9])[CH2:3]1.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH3:12].[F:20][C:21]([F:29])([F:28])[C:22]1[CH:26]=[C:25]([NH2:27])[NH:24][N:23]=1>FC(F)(F)C(O)=O>[CH3:12][C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:4](=[O:9])[CH2:3][C:2]([CH3:1])([CH3:10])[CH2:7][C:6]=2[NH:27][C:25]2=[N:24][NH:23][C:22]([C:21]([F:29])([F:28])[F:20])=[C:26]12

Komponenten

5

Edukt 3

HCID 7410AcetophenoneHCID 31358DimedoneHCID 178507669HCID 178507669, Verbindung

Produkt 1

HCID 1362053284,7,7-trimethyl-4-phenyl-3-(trifluoromethyl)-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-b]quinolin-5(4H)-oneAusbeute 0,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

In a 25 mL rb flask, 5,5-dimethylcyclohexane-1,3-dione (1402.0 mg, 10.0 mmol, 1.0 equivalent) was dissolved in trifluoroacetic acid (10.0 mL, 0.47 molar), followed by addition of acetophenone (11.44 mL, 100.0 mmol, 10.0 equivalent) in one portion. The reaction was refluxed for 3 hours at 190° C., followed by addition of 3-(trifluoromethyl)-1H-pyrazol-5-amine (1511.0 mg, 10.0 mmol, 1.5 equivalent) and continued reflux for additional 2.5 hours at 190° C. The reaction mixture was cooled and evaporated to remove TFA. The crude reaction mixture was purified by HPLC to afford the desired product as a white solid (17.0 mg). 1H NMR (300 MHz, DMSO) δ 7.24 (d, J=7.6 Hz, 2H), 7.14 (t, J=7.6 Hz, 2H), 6.99 (t, J=7.1 Hz, 1H), 2.43 (d, J=4.7 Hz, 2H), 2.01 (d, J=15.8 Hz, 1H), 1.92 (s, 3H), 1.86 (d, J=15.8 Hz, 1H), 0.99 (s, 3H), 0.92 (s, 3H). LRMS (ESI+) (M+H): 376.24, retention time 0.67 min.

Aufarbeitung

  1. temperaturecontinued reflux for additional 2.5 hours at 190° C
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. customto remove TFA
  5. customThe crude reaction mixture
  6. customwas purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-63b7514a2fbf41f587f173e6166f1195
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096594B2

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