Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 3-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)Aniline | HCID 2735391 | — |
| Reactant | 2-[4-(Trifluoromethoxy)phenyl]acetic acid | HCID 2777319 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 15896224 | HCID 15896224 | 68% |
Reaction Steps
A solution of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (35 mg, 0.14 mmol) and triethylamine (23 μL, 0.17 mmol) in DMF (0.5 mL) was added in one portion to a stirred solution of 4-trifluoromethoxyphenylacetic acid (31 mg, 0.14 mmol), HBTU (53 mg, 0.14 mmol) and HOBT (19 mg, 0.14 mmol) in DMF (1 mL). The mixture was heated at 70° C. for 24 h and then quenched with aqueous sodium bicarbonate solution. Ethyl acetate was added and the organic phase separated, washed with water (.times.3), brine, dried (MgSO4) and evaporated. Chromatography on flash silica (50% EtOAc/hexane) gave the title compound as a colourless solid (43 mg, 68%). m.p. 141.2-142.5° C. (EtOAc/hexane).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07368539B2 |
|---|
| Source dataset | uspto-grants-2008_05 |
|---|
| ORD ID | ord-32640a06c1b14f98912d5bfc01166459 |
|---|
| Source note | uspto-grants-2008_05 |
|---|
