Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine | HCID 2777760 | — |
| Reactant | HCID 68777910 | HCID 68777910 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 68779474 | HCID 68779474 | 23.9% |
Reaction Steps
A mixed solution of 2,2,2-trichloroethyl 1H-indol-5-ylcarbamate (227 mg, 0.738 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.129 ml, 0.738 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 3 hours, and then stirred at 70° C. for 18 hours. Water was poured to the reaction mixture, and the resulting solution 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 (hexane: ethyl acetate=1:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 71.3 mg (23.9%) of the desired product as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07851473B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-3a8999c2a486457db9eb7931d1cfd5b4 |
|---|
| Source note | uspto-grants-2010_12 |
|---|