Dimethyl Sulfoxide → HCID 68780989, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25](N3CCNCC3)[S:26][CH:27]=2)=[CH:19][CH:18]=1.C([N:37]([CH:40]([CH3:42])C)[CH2:38][CH3:39])(C)C.O.[CH3:44]S(C)=O>>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[N:24]=[C:25]([CH:44]3[CH2:39][CH2:38][N:37]([C:8]([NH:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:40][CH2:42]3)[S:26][CH:27]=2)=[CH:21][CH:22]=1Participants
6
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (226 mg, 0.839 mmol), 1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]piperazine (200 mg, 0.762 mmol) and diisopropylethylamine (0.266 ml, 1.52 mmol) in dimethylsulfoxide (2.5 ml) was stirred at 70° C. for 14 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, 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 ethyl acetate to give the desired product (170 mg, 58.2%) 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)
- customrecrystallized from a mixed solvent of hexane and ethyl acetate
Sources & evidence
- ORD record
- ord-53fbc6f27b904d0d9398fad2f93305cb
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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