Reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:26][CH:27]=2)=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]([N:28]3[CH2:29][CH2:30][N:31]([C:8]([NH:7][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)=[O:15])[CH2:32][CH2:33]3)[S:26][CH:27]=2)=[CH:19][CH:18]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture if 2,2,2-trichloroethyl pyrazin-2-ylcarbamate (226 mg, 0.835 mmol), 4-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]piperazine (200 mg, 0.760 mmol) and diisopropylethylamine (0.265 ml, 1.52 mmol) in dimethylsulfoxide (2.5 ml) was stirred at 70° C. for 3 days. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was wash washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the desired product (99.7 mg, 34.0%) as a solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was wash
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified silica gel column chromatography (ethyl acetate)
- customrecrystallized from a mixed solvent of hexane and tetrahydrofuran
Sources & evidence
- ORD record
- ord-996151c7ada64869bae11e6fd38fd5fa
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Linked notes
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