1,4-diphenyl-1H-imidazole → 2-(1,4-diphenyl-1H-imidazol-2-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone

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Reaktionsgleichung

C([Li])CCC.[C:6]1([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[CH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[CH2:29][CH2:28]1)=[O:26].[Cl-].[NH4+].[Na]>C1COCC1>[C:6]1([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[C:13]2[CH2:24][C:25]([N:27]2[CH2:28][CH2:29][N:30]([C:33]3[N:34]=[CH:35][CH:36]=[CH:37][N:38]=3)[CH2:31][CH2:32]2)=[O:26])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

0.5 mL butyllithium (1.6 mol/L in THF) was added to 0.15 g 1,4-diphenyl-1H-imidazole in 10 mL THF at −78° C. under argon. The reaction was stirred 40 min at −78° C. and 0.22 g 2-bromo-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanon was added to the reaction. After stirring 1 h at −78° C. the reaction was decomposed with saturated sodiumammoniumchloride solution. The mixture was extracted with ethyl acetate. The organic layer was dried and evaporated. The residue was purified by chromatography on Alox (gradient: dichlormethane/EtOAC/MeOH 9:2:0-50:45:5) to yield 20 mg of the desired compound. Rt: 1.13 (method B), (M+H)+: 425

Aufarbeitung

stirringAfter stirring 1 h at −78° C. the reaction
extractionThe mixture was extracted with ethyl acetate
customThe organic layer was dried
customevaporated
customThe residue was purified by chromatography on Alox (gradient: dichlormethane/EtOAC/MeOH 9:2:0-50:45:5)

Quellen und Nachweise

ORD-Eintrag: ord-902ec9a6b65642d8829e509314723d0e
Quelldatensatz: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08937176B2

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