関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 2-Methyl-5-Nitroaniline | HCID 7444 | — |
| 反応物 | Stannous chloride dihydrate | HCID 61436 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| 反応物 | HCID 178524710 | HCID 178524710 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | N-(5-Amino-2-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide | HCID 57567293 | 8% |
反応手順
To a solution of 4-hydroxy-quinoline-3-carboxylic acid (A-1) (50 mg, 0.26 mmol), HBTU (99 mg, 0.26 mmol) and DIEA (138 μL, 0.79 mmol) in THF (2.6 mL) was added 2-methyl-5-nitro-phenylamine (40 mg, 0.26 mmol). The mixture was heated at 150° C. in the microwave for 20 min and the resulting solution was concentrated. The residue was dissolved in EtOH (2 mL) and SnCl2.2H2O (293 mg, 1.3 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was basified with sat. NaHCO3 solution to pH 7-8 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was dissolved in DMSO and purified by HPLC (10-99% CH3CN/H2O) to yield the product, N-(5-amino-2-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (94) (6 mg, 8%). HPLC ret. time 2.06 min, 10-99% CH3CN, 5 min run; ESI-MS 294.2 m/z (MH+).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08829204B2 |
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| 出典データセット | uspto-grants-2014_09 |
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| ORD ID | ord-93b084af9c8b4076b9ce5a1f26dc07d4 |
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| 出典メモ | uspto-grants-2014_09 |
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