Water → HCID 68777416, compound
Reaction equation
[CH3:1][N:2]1[C:6]([N:7]([C:15]([O:17]CC(Cl)(Cl)Cl)=O)C(OC(Cl)(Cl)Cl)=O)=[CH:5][CH:4]=[N:3]1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:31]=[C:32]([N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[S:33][CH:34]=2)=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:31]=[C:32]([N:35]3[CH2:36][CH2:37][N:38]([C:15]([NH:7][C:6]4[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=4)=[O:17])[CH2:39][CH2:40]3)[S:33][CH:34]=2)=[CH:26][CH:25]=1Participants
6
Conditions
- Temperature
- 70 °C
Procedure
A mixture of trichloromethyl 2,2,2-trichloroethyl (1-methyl-1H-pyrazol-5-yl)imidodicarbonate (255 mg, 0.570 mmol), 4-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]piperazine (300 mg, 1.14 mmol) and diisopropylethylamine (0.198 ml, 1.14 mmol) in dimethyl sulfoxide (3.8 ml) was stirred at 70° C. for 18 hours. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over magnesium sulfate anhydrous, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 87.1 mg (39.6%) 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 magnesium sulfate anhydrous
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate)
- customrecrystallized from a mixed solvent of hexane and tetrahydrofuran
Sources & evidence
- ORD record
- ord-6d6b00d2e3df469c87262fa7f76154cb
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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