Dimethyl Sulfoxide → Methyl 6-(((5-methyl-3-phenylisoxazol-4-yl)methyl)amino)nicotinate

HRID 83288

Reaktionsgleichung

[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1NC.Cl[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1.[CH:26]([N:29](CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:16]([NH:29][CH2:26][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:17][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of (5-methyl-3-phenyl-4-isoxazolyl)-methylamine (200 mg, 1.06 mmol), methyl 6-chloronicotinate (182 mg, 1.06 mmol), N,N-diisopropyl ethyl amine (364 μL, 2.13 mmol) and DMSO (2 mL) was heated in the microwave to 160° C. for 0.5 h. It was diluted with ethyl acetate (8 mL) and washed with aqueous sodium carbonate (saturated, 8 mL), water (8 mL) and brine (8 mL). The combined aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (158 mg, 46%) as a light yellow oil. MS: m/e=324.3 [M+H]+.

Aufarbeitung

washwashed with aqueous sodium carbonate (saturated, 8 mL), water (8 mL) and brine (8 mL)
extractionThe combined aqueous layers were extracted with ethyl acetate (10 mL)
dry with materialthe combined organic layers were dried over sodium sulfate
concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

Quellen und Nachweise

ORD-Eintrag: ord-d6f0e4ff98fb4548b255d2fe6f0dd391
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846719B2

Verknüpfte Notizen

Wird geladen…