Potassium Carbonate → ethyl (2E)-3-(5-{[(3R)-1-cyclohexyl-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

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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.Cl.Cl.[CH:17]1([N:23]2[CH2:27][CH2:26][C@@H:25]([NH2:28])[CH2:24]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:17]1([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:2]3[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=3)[CH2:24]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a solution of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (416 mg) in DMF (10 mL) was added (3R)-1-cyclohexyl-3-pyrrolidinamine dihydrochloride (849 mg) and K2CO3 (1.35 g). After stirring for 2 hours at 120° C., the reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with H2O, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(5-{[(3R)-1-cyclohexyl-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (318 mg). 1H-NMR (300 MHz, CDCl3) δ 1.11-1.34 (6H, m), 1.32 (3H, t, J=7 Hz), 1.57-2.09 (6H, m), 2.30-2.44 (2H, m), 2.67-2.74 (1H, m), 2.78-2.84 (1H, m), 2.98-3.06 (1H, m), 4.25 (2H, q, J=7 Hz), 4.39-4.50 (1H, m), 5.32 (1H, d, J=8 Hz), 6.68 (1H, d, J=16 Hz), 7.57 (1H, d, J=16 Hz), 7.88 (1H, d, J=1 Hz), 8.06 (1H, d, J=1 Hz).

Aufarbeitung

customthe reaction mixture was partitioned between ethyl acetate and H2O
washThe organic layer was washed with H2O
dry with materialdried over MgSO4
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-68ef71621e864ff681ea0fa43fa21a43
Quelldatensatz: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07557127B2

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