Dimethyl Sulfoxide → N-[4-(2-oxopyrrolidin-1-yl)phenyl]-4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide
Reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([N:13]([C:22]([O:24]CC(Cl)(Cl)Cl)=O)C(OCC(Cl)(Cl)Cl)=O)=[CH:9][CH:8]=1.[C:30]1([C:36]2[N:37]=[C:38]([N:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)[S:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:22]([N:44]2[CH2:45][CH2:46][N:41]([C:38]3[S:39][CH:40]=[C:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:37]=3)[CH2:42][CH2:43]2)=[O:24])=[CH:11][CH:12]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of bis(2,2,2-trichloroethyl) [4-(2-oxopyrrolidin-1-yl)phenyl]imidodicarbonate (200 mg, 0.379 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (196 mg, 0.758 mmol), diisopropylethylamine (0.132 ml, 0.758 mmol) and dimethyl sulfoxide (4 ml) was stirred at 70° C. for 24 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, and the residue was recrystallized from ethyl acetate to give 116 mg (68.2%) of the desired product 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 recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-0ee3de035623480993988107af2a96e6
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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