참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | 2-Methyl-5-Nitroaniline | HCID 7444 | — |
| 반응물 | Stannous chloride dihydrate | HCID 61436 | — |
| 반응물 | Diisopropylethylamine | HCID 81531 | — |
| 반응물 | Sodium Bicarbonate | HCID 516892 | — |
| 반응물 | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| 반응물 | HCID 178524710 | HCID 178524710 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | N-(5-Amino-2-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide | HCID 57567293 | 8% |
반응 단계
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+).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08829204B2 |
|---|
| 출처 데이터셋 | uspto-grants-2014_09 |
|---|
| ORD ID | ord-93b084af9c8b4076b9ce5a1f26dc07d4 |
|---|
| 출처 메모 | uspto-grants-2014_09 |
|---|
