Dimethyl Sulfoxide → N-Isoxazol-5-yl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
Reaction equation
[O:1]1[C:5]([NH:6][C:7](=[O:14])OCC(Cl)(Cl)Cl)=[CH:4][CH:3]=[N:2]1.[C:15]1([C:21]2[N:25]=[C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[S:23][N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:1]1[C:5]([NH:6][C:7]([N:29]2[CH2:30][CH2:31][N:26]([C:24]3[S:23][N:22]=[C:21]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:25]=3)[CH2:27][CH2:28]2)=[O:14])=[CH:4][CH:3]=[N:2]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2,2,2-trichloroethyl isoxazol-5-ylcarbamate (200 mg, 0.771 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (190 mg, 0.771 mmol), diisopropylethylamine (0.134 ml, 0.771 mmol) and dimethylsulfoxide (7 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 tetrahydrofuran, ethyl acetate and hexane to obtain the desired product (61.5 mg, 22.4%) as a solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate)
Sources & evidence
- ORD record
- ord-6b69816db2f8489399769f4ceb85127f
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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