Acetonitrile → (4-Methyl-benzyl)-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-amine

HRID 8685

Reaktionsgleichung

Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1.C(#N)C>C(OCC)(=O)C.ClCCl>[CH3:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:32][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]3[C:16]4[S:17][CH:18]=[CH:19][C:15]=4[O:14][N:13]=3)[CH:7]=2)=[CH:29][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

Mix 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole (0.400 g, 1.18 mmol), potassium carbonate (0.326 g, 2.36 mmol), 4-methylbenzylamine (0.606, 5.00 mmol) and acetonitrile (5.0 mL) and heat (75° C.), overnight. Cool the reaction mixture and filter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate). Combine the appropriate fractions and concentrate to give a residue. Dissolved residue in 50% ethyl acetate in dichloromethane and chromatograph on silica (10 g) using ethyl acetate to give the title compound (356 mg, 80% yield). Purity by LC/MS (APCI)=98, [M+H]+=379.

Aufarbeitung

temperatureCool the reaction mixture
filtrationfilter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate)
concentrationCombine the appropriate fractions and concentrate
customto give a residue

Quellen und Nachweise

ORD-Eintrag: ord-a99c1c0c4a2345f79a71dc7c55462a97
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091199B1

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