Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Fluorobenzoyl chloride | HCID 67879 | — |
| Reactant | HCID 86675991 | HCID 86675991 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86675993 | HCID 86675993 | 82% |
Reaction Steps
To a solution of 3-amino-N-[2,6-diethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)phenyl]-4-(1,2,4-triazol-1-yl)benzamide (75 mg, 0.15 mmol) (Example I4) in dichloromethane (3 ml) was added triethylamine (63 μl, 0.45 mmol) and 4-fluorobenzoyl chloride (21.3 μl, 0.18 mmol). The reaction mixture was heated to reflux for 15 hours. The reaction mixture was cooled to ambient temperature and quenched by addition of saturated aqueous sodium hydrogen carbonate (5 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (2×5 ml). The combined organic phases were dried over sodium sulfate and concentrated. The residue was purification by column chromatography on silica gel (eluent: hexane/ethyl acetate 1:4) to give Compound No. D2 of Table D (76 mg, 82% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08455399B2 |
|---|
| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-40e0c9c9281c4278bd977c3a111d143d |
|---|
| Source note | uspto-grants-2013_06 |
|---|