Diisopropylethylamine → Gsk163090

HRID 15822

Reaktionsgleichung

CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][CH2:17][NH:16][C:15]2=[O:19])[CH:9]=1)(=O)=O.[CH3:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[N:22]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[N:31]2[CH2:36][CH2:35][N:34]([CH2:6][CH2:7][C:8]3[CH:9]=[C:10]([N:14]4[CH2:18][CH2:17][NH:16][C:15]4=[O:19])[CH:11]=[CH:12][CH:13]=3)[CH2:33][CH2:32]2)[N:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

2-[3-(2-Oxo-1-imidazolidinyl)phenyl]ethyl methanesulfonate (1.32 wt) and 2-methyl-5-(1-piperazinyl)quinoline (1 wt.) were suspended in acetonitrile (5 vol) at room temperature under nitrogen. Diisopropylethylamine (1.53 vol) was added dropwise over 30 minutes, and the mixture was then stirred at 75° C. for 4 hours. The reaction mixture was cooled to room temperature, concentrated to 2 vol, and diluted with ethyl acetate (7 vol). The organic layer was washed with saturated aqueous ammonium chloride solution (2×3 vol), followed by water (1×3 vol). The organic layer was evaporated to dryness, yielding the title compound as a brown foam (70% th).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated to 2 vol
additiondiluted with ethyl acetate (7 vol)
washThe organic layer was washed with saturated aqueous ammonium chloride solution (2×3 vol)
customThe organic layer was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-af166f26abae404db23b390200021af7
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07732600B2

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