Potassium Carbonate → ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-piperidinyl]amino}2-pyrazinyl)acrylate
Reaktionsgleichung
Cl[C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH2:36])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH:36][C:2]2[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=2)[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
To a solution of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (300 mg) and potassium carbonate (4.94 mg) in DMF (15 mL) was added (3R)-1-benzyl-3-piperidinamine dihydrochloride (668 mg) under nitrogen at ambient temperature and the mixture was stirred at 85° C. for 18 hrs. The reaction mixture was evaporated in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform-MeOH=97-3) to give ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-piperidinyl]amino}-2-pyrazinyl)acrylate (125 mg) as an oil.
Aufarbeitung
- customThe reaction mixture was evaporated in vacuo
- customthe residue was partitioned between water and ethyl acetate
- washThe organic layer was washed with water and brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residue was purified by silica gel column chromatography (chloroform-MeOH=97-3)
Quellen und Nachweise
- ORD-Eintrag
- ord-82c5cf8b1c5b4d4a99c674a0c870b3dd
- Quelldatensatz
- uspto-grants-2008_12
- Patentnummer
- US07465731B2
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