HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrazole, 4-amino-3,5-dimethyl- → 5-{[2,4-dichloro-5-(pyridin-2-yl)benzoyl]amino}-N-(3,5-dimethyl-1H-pyrazol-4-yl)-1-phenyl-1H-pyrazole-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyrazole, 4-amino-3,5-dimethyl- | HCID 78931 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid | HCID 118497035 | — |
| Reactant | HCID 178484293 | HCID 178484293 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-{[2,4-dichloro-5-(pyridin-2-yl)benzoyl]amino}-N-(3,5-dimethyl-1H-pyrazol-4-yl)-1-phenyl-1H-pyrazole-3-carboxamide | HCID 118497125 | 49.6% |
Reaction Steps
To a solution of 5-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 111, 110 mg, 0.24 mmol), 3,5-dimethyl-1H-pyrazol-4-amine (30 mg, 0.27 mmol) and DIPEA (0.17 mL, 0.97 mmol) in DMF (1.5 mL) was added 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (101 mg, 0.26 mmol) and the reaction was stirred for 2 hours at room temperature. The reaction was concentrated in vacuo and the residue purified using Preparative HPLC to afford the title compound (65 mg, 49%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09328096B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-f765d43d60414545b93aa72d2a169944 |
| Source note | uspto-grants-2016_05 |