Sodium Carbonate → 2-ethylsulfanyl-N-(2-propylamino-5-trifluoromethylpyridin-3-yl)-benzamide

HRID 533660

Reaktionsgleichung

[CH2:1]([NH:4][C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1)[CH2:2][CH3:3].[CH2:16]([S:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22])[CH3:17].CCN=C=NCCCN(C)C.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[CH2:16]([S:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:11][C:10]1[C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[N:6][CH:7]=[C:8]([C:12]([F:15])([F:13])[F:14])[CH:9]=1)=[O:22])[CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A mixture of N-propyl-5-trifluoromethylpyridin-2,3-diamine (770 mg), 2-ethylsulfanyl-benzoic acid (700 mg), WSC (740 mg), and pyridine (20 ml) was stirred with heating at 95° C. for 7 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 422 mg of 2-ethylsulfanyl-N-(2-propylamino-5-trifluoromethylpyridin-3-yl)-benzamide (Compound (1B)-513).

Aufarbeitung

temperatureInto the reaction mixture cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-cd2ed6b2e12143f19e7fedbe820a8f9e
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08853238B2

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