Trifluoroacetic acid → HCID 71008950, Verbindung

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Reaktionsgleichung

[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][C:18]([F:34])([F:33])[O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][CH:29]=[CH:28][C:27]2=[O:32])=[CH:22][CH:21]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][CH:29]2[CH:28]([C:27](=[O:32])[N:26]([C:23]3[CH:22]=[CH:21][C:20]([O:19][C:18]([F:17])([F:34])[F:33])=[CH:25][CH:24]=3)[CH2:31][CH2:30]2)[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To N-benzyl(methoxy)-N-((trimethylsilyl)methyl)methanamine (1.7 g, 7.0 mmol) and 1-(4-trifluoromethoxy-phenyl)-5,6-dihydro-1H-pyridin-2-one (0.6 g, 2.3 mmol) in DCM (30 mL) was added a solution of trifluoroacetic acid (0.026 g, 0.23 mmol) in DCM (10 mL) at 4° C. After the mixture was stirred at 50° C. for 3 h, the solution was washed with saturated sodium bicarbonate and brine, then dried over anhydrous Na2SO4. After removal of the DCM, the residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate P (10:1 to 5:1) to yield the title compound (0.19 g, 21%). 1H NMR (300 MHz, CDCl3): δ 7.34-7.20 (m, 9H), 3.77-3.55 (m, 4H), 3.18-3.01 (m, 2H), 2.93-3.83 (m, 3H), 2.43-2.41 (m, 1H), 2.07-2.05 (m, 1H), 1.80-1.75 (m, 1H); LC-MS: [M+1]+ 391.1.

Aufarbeitung

washthe solution was washed with saturated sodium bicarbonate and brine
dry with materialdried over anhydrous Na2SO4
customAfter removal of the DCM
customthe residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate P (10:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag: ord-af21e24d68cd4c1888223403987272e5
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08501768B2

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