Piperidine → HCID 178503482, compound

HRID 624768Notes

Reaction equation

HRID 624768 reaction equation
[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

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 58196600HCID 58196600, compound

Product 1

HCID 178503482HCID 178503482, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-e3ff4daa481348e3b8658469a53b641e
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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