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 (×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 | US06107324 |
|---|
| Source dataset | uspto-grants-2000_08 |
|---|
| ORD ID | ord-043f9dce024b4ddca375385a1d0d73ca |
|---|
| Source note | uspto-grants-2000_08 |
|---|
