Water → HCID 67025457, Verbindung

HRID 217272

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([NH2:20])=[C:18](Br)[C:17]([Cl:22])=[C:16]([C:23]([F:26])([F:25])[F:24])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C1(C)C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([NH2:20])=[CH:18][C:17]([Cl:22])=[C:16]([C:23]([F:24])([F:25])[F:26])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

A solution of the compound obtained in Step B (0.2 g), tris(trimethylsilyl)-silane (0.16 ml), and 2,2′-azobis(2-methylpropionitrile) (10 mg) in toluene (10 ml) was stirred at 85° C. for 2 hours under a nitrogen atmosphere. More tris(trimethylsilyl)silane (0.3 ml) and more 2,2′-azobis(2-methylpropionitrile) (5 mg) were then added and the reaction mixture was heated to 85° C. for 16 hours. The reaction mixture was cooled to ambient temperature, poured into water, extracted with ethyl acetate, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane/ethyl acetate 1:1) afforded 3-amino-5-chloro-6-trifluoromethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.160 g) as a solid. MS (ES+) 324/326 (M-isoprene); 1H NMR (400 MHz, CDCl3) 1.48 (s, 9H), 1.84 (m, 4H), 2.78 (m, 1H), 2.88 (m, 2H), 4.25 (m, 2H), 4.42 (s, 2H), 7.46 (s, 1H).

Aufarbeitung

temperatureThe reaction mixture was cooled to ambient temperature
extractionextracted with ethyl acetate
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-9fbe68e98dfb40c395ffb8d6e2a87586
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08193362B2

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