HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → (2-{(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | N-(tert-Butoxycarbonyl)-1,2-phenylenediamine | HCID 676311 | — |
| Reactant | (E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]acrylic acid | HCID 68524810 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | (2-{(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester | HCID 86621696 | — |
Reaction Steps
A mixture of 3.1 g (E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid with 170 ml DMF and 1.3 g HOBt.H2O and 12.0 ml triethylamine is stirred for 0.5 h. Then 4.9 g EDC.HCL is added and the suspension is stirred again at ambient temperature for 0.5 h. After that 1.8 g (2-amino-phenyl)-carbamic acid tert-butyl ester are added and the mixture is stirred at ambient temperature for 24 h. The DMF is evaporated and the residue is extracted with ethyl acetate and water. The organic layer is dried over sodium sulfate. The title compound is isolated by flash chromatography.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815855B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-b45f6a8fdd5d430aaa2e62cb67757c29 |
| Source note | uspto-grants-2014_08 |