Reaction equation
ClC(Cl)(Cl)CO[C:5](=[O:17])[NH:6][C:7]1[CH:8]=[N:9][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:11][CH:12]=1.[C:20]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:25]=[CH:24][CH:23]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:21]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:14]([NH:13][C:10]1[N:9]=[CH:8][C:7]([NH:6][C:5]([N:29]2[CH2:30][CH2:31][N:26]([C:22]3[CH:21]=[C:20]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:25]=[CH:24][CH:23]=3)[CH2:27][CH2:28]2)=[O:17])=[CH:12][CH:11]=1)(=[O:16])[CH3:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixed solution of 2,2,2-trichloroethyl[6-(acetylamino)pyridin-3-yl]carbamate (301 mg, 0.923 mmol), 1-biphenyl-3-ylpiperazine (200 mg, 0.839 mmol) and diisopropylethylamine (0.292 ml, 1.68 mmol) in dimethylsulfoxide (2.5 ml) was stirred at 70° C. for 14 hours. To the reaction solution was added water, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduce pressure. The residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the titled compound (62.6 mg, 18.0%) as solid product.
Workup
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled away
- customThe residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran
Sources & evidence
- ORD record
- ord-1c9d480f075c46bcae5ed1acf7146185
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812025B2
Linked notes
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