Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | 1,1'-Thiocarbonyldiimidazole | HCID 80264 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | tert-Butyl 4-carbamothioylpiperazine-1-carboxylate | HCID 12093220 | — |
| Reactant | 2-(Benzenesulfonyl)-3-(trifluoromethyl)oxirane | HCID 21100218 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67549316 | HCID 67549316 | 26% |
Reaction Steps
To a solution of 17.5 mmol 2-benzenesulfonyl-3-trifluoromethyl-oxirane in 20 ml N,N-dimethylformamide was added 15.9 mmol 4-thiocarbamoyl-piperazine-1-carboxylic acid tert-butyl ester (prepared from tert-butyl 1-piperazinecarboxylate, 1,1′-thiocarbonyldiimidazole and ammonia according to the procedure of J. Med. Chem. 1998, 41, 5037–5054). The mixture was heated at 90° C. for 10 h. The reaction mixture was then concentrated in vacuo and the residue purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as an orange crystalline solid (yield 26%). MS (m/e): 338.1 (M+H+, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07220744B2 |
|---|
| Source dataset | uspto-grants-2007_05 |
|---|
| ORD ID | ord-eddb781fa26e4d88b48c42e1c0bcecc0 |
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| Source note | uspto-grants-2007_05 |
|---|
