HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → (RS)-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-(2-oxo-2lambda4-[1,2,3]oxathiazolidin-3-yl)-pyridin-3-yl]-N-methyl-isobutyramide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 2-(3,5-bis(trifluoromethyl)phenyl)-N-(4-(2-chlorophenyl)-6-(2-hydroxyethylamino)pyridin-3-yl)-N,2-dimethylpropanamide | HCID 10303099 | — |
| Solvent | Water | HCID 962 | — |
| Product | (RS)-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-(2-oxo-2lambda4-[1,2,3]oxathiazolidin-3-yl)-pyridin-3-yl]-N-methyl-isobutyramide | HCID 86597718 | 77.9% |
Reaction Steps
To a solution of 0.20 g (0.36 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-(2-hydroxy-ethylamino)-pyridin-3-yl]-N-methyl-isobutyramide in a 5 ml dichloromethane were added consecutively 0.11 g (1.1 mmol) triethylamine and 0.05 g (0.4 mmol) thionyl chloride at room temperature. After 1 h the reaction mixture was diluted with water and extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 0.17 g (77%) of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07939533B2 |
| Source dataset | uspto-grants-2011_05 |
| ORD ID | ord-23bc7889eb824a66804347153f057422 |
| Source note | uspto-grants-2011_05 |