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Diisopropylethylamine → 1-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (7-chloro-2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | PyBroP | HCID 2733179 | — |
| 反応物 | 1-Benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid | HCID 18179616 | — |
| 反応物 | 3-aminomethyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one | HCID 71208332 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 1-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (7-chloro-2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide | HCID 71217329 | — |
反応手順
In a 10 mL round-bottomed flask, 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (32.6 mg, 0.142 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (66.3 mg, 0.142 mmol) and N,N-diisopropylethylamine (73.5 mg, 0.099 mL, 0.569 mmol) were combined with DMF (2 mL). The reaction mixture was stirred at room temperature for 10 min. After this time, 3-aminomethyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one (intermediate A) was added (0.050 g, 0.142 mmol). The reaction mixture was stirred at room temperature for 3 hr. The product was purified using flash chromatography (40% ethyl acetate/hexane ramped to 100% ethyl acetate/hexanes). MS calcd. for C32H24ClN4O4 [(M+H)+] 563.1, obsd. 563.3.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08501732B2 |
| 出典データセット | uspto-grants-2013_08 |
| ORD ID | ord-8a717c4bc36a4e079b40f4554f59b3c0 |
| 出典メモ | uspto-grants-2013_08 |