Piperidine → HCID 178503482, Verbindung

HRID 624768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624768
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=O)=[C:9]3[N:8]=[C:7]([S:16][CH3:17])[N:6]=2)[CH2:3][CH2:2]1.[NH:18]1[CH2:24][C:22](=[O:23])[NH:21][C:19]1=[O:20].N1CCCCC1>C(O)C>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:24]4/[C:22](=[O:23])[NH:21][C:19](=[O:20])[NH:18]/4)=[C:9]3[N:8]=[C:7]([S:16][CH3:17])[N:6]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 10006HydantoinHCID 58196600HCID 58196600, Verbindung

Produkt 1

HCID 178503482HCID 178503482, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-(Cyclopropylamino)-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine-8-carbaldehyde (1.0 eq, 3.00 g, 12.03 mmol) was suspended in ethanol (40 ml). Hydantoin (1.5 eq, 1.81 g, 18.08 mmol) and piperidine (1.5 eq, 1.78 ml, 18.01 mmol) were added. The mixture was heated at reflux under vigorous magnetic stirring for 3 hours. After cooling of the reaction mixture, the precipitate was filtered, washed with ethanol, then with a mixture of ethanol and water (1:1). After drying in vacuo, (Z)-5-((4-(cyclopropylamino)-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione was isolated as a yellow solid (3.80 g, 95%). LCMS (ES): >85% pure, m/z 332 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux under vigorous
  3. temperatureAfter cooling of the reaction mixture
  4. filtrationthe precipitate was filtered
  5. washwashed with ethanol
  6. additionwith a mixture of ethanol and water (1:1)
  7. customAfter drying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e3ff4daa481348e3b8658469a53b641e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303033B2

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