Acetonitrile → 4-Cyano-N-(2-{7-[2-(2-fluoro-phenoxy)-ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}-ethyl)-N-methyl-benzenesulfonamide

HRID 1992402

Reaktionsgleichung

Cl.Cl.[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH3:26])[CH2:15][CH2:16][N:17]2[CH2:24][CH:23]3[O:25][CH:19]([CH2:20][NH:21][CH2:22]3)[CH2:18]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)#[N:4].Br[CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[F:37].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH2:15][CH2:16][N:17]2[CH2:24][CH:23]3[O:25][CH:19]([CH2:20][N:21]([CH2:28][CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[F:37])[CH2:22]3)[CH2:18]2)[CH3:26])(=[O:13])=[O:12])=[CH:7][CH:6]=1)#[N:4]

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

To 4-cyano-N-methyl-N-[2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethyl]-benzenesulfonamide dihydrochloride (0.127 g, 0.30 mmol, prep I above), 1-(2-bromo-ethoxy)-2-fluoro-benzene (0.069 g, 0.315 mmol;) and potassium carbonate (0.145 g, 1.05 mmol) was added acetonitrile (4 mL) and water (0.1 mL). The mixture was heated by microwave irradiation (10 minutes, 160° C.) and was then filtered and evaporated. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 85 mg (58.0%) of the title compound.

Aufarbeitung

filtrationwas then filtered
customevaporated
customThe crude product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-fec54478f9c04f31973031cb30395e37
Quelldatensatz: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07648985B2

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