Dimethyl Sulfoxide → HCID 68777886, 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:18]=[C:19]([C:23]2[N:24]=[C:25](N3CCNCC3)[S:26][CH:27]=2)[CH:20]=[CH:21][CH:22]=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]=[C:19]([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:20]=[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-(3-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 3 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 magnesium sulfate anhydrous, and the solvent distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the desired product (280 mg, 96.1%) as an oil.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate anhydrous
- distillationthe solvent distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate)
Sources & evidence
- ORD record
- ord-680f36dcf8ea49fcaa88c2cf71126735
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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