Dimethyl Sulfoxide → N-{4-[Acetyl(methyl)amino]phenyl}-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

A solution of 2,2,2-trichloroethyl {4-[acetyl(methyl)amino]phenyl}carbamate (200 mg, 0.589 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (145 mg, 0.589 mmol), diisopropylethylamine (0.103 ml, 0.589 mmol) and dimethylsulfoxide (4 ml) was stirred at 70° C. for 12 hours, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain the desired product as a solid. This was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (47.3 mg, 18.3%) as a solid.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe extract was washed with water
3. dry with materialdried over anhydrous magnesium sulfate
4. distillationThe solvent was distilled off under reduced pressure
5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

ORD-Eintrag

ord-fcf4cdc5076c4ac088906b41d542d27e

Quelldatensatz

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07851473B2