Potassium Carbonate → 2,2-Dimethylpropyl 4-[4-(5-methyl-1,2,4-triazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate

HRID 421831

Reaktionsgleichung

Reaktionsgleichung von HRID 421831
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[CH:4]=1)#[N:2].[C:23](O)(=O)[CH3:24].[NH2:27][NH2:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[CH3:24][C:23]1[NH:28][N:27]=[C:1]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([N:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:13][CH2:14]3)[CH:4]=2)[N:2]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 165591Hydrazine, acetate (1:1)HCID 119924192,2-Dimethylpropyl 4-(4-cyanopyridin-2-yl)-1-piperazinecarboxylate

Produkt 1

HCID 119928952,2-Dimethylpropyl 4-[4-(5-methyl-1,2,4-triazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylateAusbeute 4,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2,2-Dimethylpropyl 4-(4-cyanopyridin-2-yl)piperazine-1-carboxylate (143 mg) obtained in Example 2 was dissolved in ethanol (5 mL), and hydrazine acetate (140 mg) and potassium carbonate (328 mg) were added thereto and heated under reflux for 5 hours, then the reaction liquid was evaporated. Acetic anhydride (3 mL) was added to the resulting residue, and heated under reflux for 2 hours, then the reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (chloroform/methanol=9/1) to obtain 7.6 mg of the entitled compound as a colorless oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. customthe reaction liquid
  4. customwas evaporated
  5. additionAcetic anhydride (3 mL) was added to the resulting residue
  6. temperatureheated
  7. temperatureunder reflux for 2 hours
  8. customthe reaction liquid
  9. washwashed with water and saturated saline water
  10. dry with materialdried with anhydrous sodium sulfate
  11. customThe solvent was evaporated away
  12. customthe resulting residue was isolated
  13. custompurified through thin-layer silica gel chromatography (chloroform/methanol=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-241f80ed593d401f8b4f89df86e1e3e7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101618B2

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