HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4,5-Difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine | HCID 735132 | — |
| Reactant | 2-Chloro-4,5-difluorobenzoic acid | HCID 737171 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4,5-Difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid | HCID 22320195 | 81% |
Reaction Steps
Under an argon atmosphere, a solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.01 g, 34.5 mmol), 2-chloro-4,5-difluorobenzoic acid (6.64 g, 34.5 mmol), copper acetate (II) (0.718 g, 3.95 mmol) and potassium carbonate (4.77 g, 34.5 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 2 hours. The solution was cooled to room temperature, and poured into water. The solution was made weakly acidic by the addition of acetic acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (9.21 g, 81% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06949648B2 |
| Source dataset | uspto-grants-2005_09 |
| ORD ID | ord-93562eff33dc4f0482610bb09e6b1e61 |
| Source note | uspto-grants-2005_09 |