HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-amino-N-(4-chloropyridin-3-yl)-6-(2,6-difluorophenyl)-5-fluoropicolinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 3-Amino-4-chloropyridine | HCID 581932 | — |
| Reactant | 3-Amino-6-(2,6-difluorophenyl)-5-fluoropicolinic acid | HCID 59226513 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 3-amino-N-(4-chloropyridin-3-yl)-6-(2,6-difluorophenyl)-5-fluoropicolinamide | HCID 69041531 | 14% |
Reaction Steps
To a solution of 4-chloropyridin-3-amine (1.0 equiv.) and 3-amino-6-(2,6-difluorophenyl)-5-fluoropicolinic acid (1.0 equiv.) in NMP (1 M) was added HOAt and EDCI sequentially. The reaction mixture was stirred at room temperature for 2 days. The crude reaction was purified by prep HPLC to give 3-amino-N-(4-chloropyridin-3-yl)-6-(2,6-difluorophenyl)-5-fluoropicolinamide (14%). LCMS (m/z): 379.0 (MH+); LC Rt=3.49 min
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822497B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-c2a9a24737da4afeb34ee92ab5fc4609 |
| Source note | uspto-grants-2014_09 |