HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Ethyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorobenzenesulfonamide | HCID 46909431 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ethyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonylcarbamate | HCID 66739854 | 68.3% |
Reaction Steps
To a mixture of 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorobenzenesulfonamide (100 mg, 0.17 mmol) and ethyl chloroformate (0.022 mL, 0.21 mmol, 1.2 eq) in DCM was added Et3N (0.05 mL, 0.34 mmol, 2.0 eq). After stirring 3 h, the reaction mixture was diluted with EtOAc, washed with water and brine, and purified by chromatography (0 to 80% EtOAc/Hex, then 10% MeOH/DCM) to give 76 mg (68%) of ethyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonylcarbamate. MS (EI): 655 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846739B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-bcc35af41068489098a6ce6678c90ae9 |
| Source note | uspto-grants-2014_09 |