HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4-(4-Trifluoromethylpyrid-3-ylcarbonylamino)-2-phenylbenzoic acid 2-trimethylsilylethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 3-hydroxy-1,2,3-benzotriazin-4(3H)-one | HCID 73026 | — |
| Reactant | 3-Pyridinecarboxylic acid, 4-(trifluoromethyl)- | HCID 2777549 | — |
| Reactant | (4-Amino-2-phenylbenzoyl)methionine 2-trimethylsilylethyl ester | HCID 67550574 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(4-Trifluoromethylpyrid-3-ylcarbonylamino)-2-phenylbenzoic acid 2-trimethylsilylethyl ester | HCID 67550687 | 87% |
Reaction Steps
A mixture of 4-trifluoromethylnicotinic acid (472 mg, 2.46 mmol), the product of Example 283B (771 mg, 2.46 mmol), 3-hydroxy1,2,3-benzotriazin-4(3H)-one (481 mg, 2.95 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (566 mg, 2.95 mmol) in DMF (8 mL) was stirred room temperature for 15 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (30% ethyl acetate-hexane) to give the title compound (1.04 g, 87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06310095B1 |
| Source dataset | uspto-grants-2001_10 |
| ORD ID | ord-2e504847da2e45d7a3f084623e24a0ac |
| Source note | uspto-grants-2001_10 |