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Diisopropylethylamine → 7-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid ethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Ethyl 7-aminoquinoline-3-carboxylate | HCID 9877801 | — |
| 反応物 | 2-(5-(Trifluoromethyl)pyridin-2-yl)benzoic acid | HCID 22736909 | — |
| 溶媒 | 1,2-Dichloroethane | HCID 11 | — |
| 溶媒 | Thionyl Chloride | HCID 24386 | — |
| 生成物 | 7-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid ethyl ester | HCID 69891345 | 85% |
反応手順
2-(5-Trifluoromethyl-pyridin-2-yl)-benzoic acid (325 mg, 1.05 mmol) was dissolved in 15 ml of thionyl chloride, and the mixture heated at 60 C. After 4 h, the volatiles were removed under vacuum, the residue combined with 7-amino-quinoline-3-carboxylic acid ethyl ester (100 mg, 0.46 mmol), dissolved in 1,2-dichloroethane (15 ml), and diisopropylethylamine (300 mg, 2.31 mmol) added. After heating at reflux for 48 h, the reaction mixture was washed with 1N HCl, dried (magnesium sulfate), filtered, and concentrated under vacuum. The resulting residue was purified by silica gel chromatography eluting with 50% ethyl acetate in hexanes to provide 180 mg (85%) of the title compound.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06713489B2 |
| 出典データセット | uspto-grants-2004_03 |
| ORD ID | ord-45cde8f8728746f0a03b36badf7735a8 |
| 出典メモ | uspto-grants-2004_03 |