HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → [4-(4-Trifluoromethylpyrid-3-ylcarboxyamino)-2-phenylbenzoyl]methionine methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| 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 methyl ester hydrochloride | HCID 69612387 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [4-(4-Trifluoromethylpyrid-3-ylcarboxyamino)-2-phenylbenzoyl]methionine methyl ester | HCID 20622816 | 57% |
Reaction Steps
A mixture of 4-trifluoromethylnicotinic acid (100 mg, 0.523 mmol), (4-amino-2-phenylbenzoyl)methionine methyl ester hydrochloride (206 mg, 0.52 mmol), prepared as in Example 192B, 3-hydroxy1,2,3-benzotriazin-4(3H)-one (120 mg, 0.628 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (125 mg, 0.628 mmol) in THF (5 mL) was stirred 15 hours. The reaction mixture was diluted with ethyl acetate , washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (50% ethyl acetate-hexane) to give the title compound (157 mg, 57%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06693123B2 |
| Source dataset | uspto-grants-2004_02 |
| ORD ID | ord-02495e4431324cab80a50704c3e290d7 |
| Source note | uspto-grants-2004_02 |