HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Methoxypyridin-4-amine | HCID 280891 | — |
| Reactant | 5-Chloro-2-fluorobenzoic acid | HCID 2736537 | — |
| 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 | Dichloromethane | HCID 6344 | — |
| Product | 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide | HCID 86728468 | 47.3% |
Reaction Steps
A solution of 5-chloro-2-fluoro-benzoic acid (5.0 g, 28.64 mmol), HATU (10.89 g, 28.64 mmol), 2-methoxypyridin-4-amine (3.6 g, 28.64 mmol) and Et3N (15.98 mL, 114.60 mmol) in dichloromethane (45.0 mL) was stirred at room temperature overnight. The crude mixture was purified by column chromatography eluting with a gradient of ethyl acetate in hexanes (0-50%) to yield 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (3.8 g, 47%) as a white solid. ESI-MS m/z calc. 280.04. found 281.3 (M+1)+; Retention time: 1.31 minutes (3 minutes run).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09393235B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-77c47faf3a134507b99b46f72af6131c |
| Source note | uspto-grants-2016_07 |