HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Rac-2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1h-imidazol-1-yl]-n-{1-[3-(trifluoromethyl)phenyl]ethyl}acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | (1R)-1-(3-(Trifluoromethyl)phenyl)ethylamine | HCID 2782448 | — |
| Solvent | Water | HCID 962 | — |
| Product | Rac-2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1h-imidazol-1-yl]-n-{1-[3-(trifluoromethyl)phenyl]ethyl}acetamide | HCID 58011689 | — |
Reaction Steps
50.0 mg (0.171 mmol) of 4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid from Example 130A, 35.5 mg (0.188 mmol) of 1-[3-(trifluoromethyl)phenyl]-ethylamine and 27.7 mg (0.205 mmol) of HOBt are placed in 1.5 ml of dimethylformamide and treated with 42.6 mg (0.222 mmol) of EDC hydrochloride. This is stirred overnight at room temperature, then stirred with 19 ml of water and the resulting precipitate recovered by filtration. The crude product is washed with water, dried in vacuo and purified by preparative HPLC [Method 9]. 14 mg (18% of theory) of the target compound are thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08084481B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-0d08feff096c4ef2af8624bc1af7db70 |
| Source note | uspto-grants-2011_12 |