Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Pyrazole-3,5-dicarboxylic acid | HCID 76559 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 5706704 | HCID 5706704 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Trifluoroacetic acid | HCID 6422 | 97% |
| Product | 5-[(R)-2-Carboxy-1-(2-trifluoromethylbenzyl)-ethylcarbamoyl]-2H-pyrazole-3-carboxylic Acid | HCID 71074298 | — |
Reaction Steps
(R)-3-Amino-4-(2-trifluoromethyl-phenyl)-butyric acid (63 mg, 260 μmol, 1.0 eq.), 3,5-pyrazoledicarboxylic acid (40 mg, 0.2 mmol, 1.0 eq.), and HATU (97 mg, 260 μmol, 1.0 eq.) were dissolved in DMF (5 mL) and stirred. DIPEA (200 μL, 4.0 eq.) was added and the resulting mixture was stirred at room temperature for 1 hour. The product was then vacuumed to dryness. This crude product was dissolved in MeOH (3 mL), and 10N NaOH (250 μL) was added. The resulting mixture was stirred at 60° C. for 1 hour. Glacial AcOH (250 μL) was added and the mixture was then vacuumed to dryness. The product was then purified by preparative HPLC to yield the title compound as a TFA salt (26.4 mg, 97% purity). MS m/z [M+H]+ calc'd for C16H14F3N3O5, 386.09. found 386.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09422245B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-48dfc8ed6e564f78ba7e02f28b6b66c7 |
|---|
| Source note | uspto-grants-2016_08 |
|---|
