With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1204-75-7,3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid,as a common compound, the synthetic route is as follows.
1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (230 mg, 1.20 mmol) and 1-hydroxybenzotriazole monohydrate (184 mg, 1.20 mmol) were added to a methylene chloride solution (10 ml) of the resulting compound (308 mg, 1.00 mmol) and 3-hydroxyquinoxaline-2-carboxylic acid (190 mg, 1.00 mmol), at room temperature, under nitrogen stream, followed by further addition of N-methylmorpholine (0.550 ml, 5.00 mmol), and stirring was carried out at room temperature overnight. The reaction solution was diluted with methylene chloride, followed by sequential washing with a saturated aqueous sodium hydrogencarbonate solution, a saturated aqueous ammonium chloride solution, water and saline, and then the resulting organic layer was dried over anhydrous sodium sulfate. After the organic layer was concentrated and the resulting residue was purified by a medium-pressure preparative liquid chromatograph (manufactured by Biotage, Inc., 25+M), the residue resulting from concentration was suspended in a mixed solvent of methylene chloride-ethyl acetate, the solid substance was collected by filtration to afford the desired title compound (126 mg, yield 26%) as a pale yellow solid. 1H-NMR (DMSO-d6, 400 MHz) delta: 12.83 (1H, brs), 9.52 (1H, d, J=7.8 Hz), 7.86 (1H, dd, J=7.4 Hz, 7.0 Hz), 7.65 (1H, dd, J=7.8 Hz, 7.4 Hz), 7.40 (1H, d, J=7.0 Hz), 7.38 (1H, d, J=7.4 Hz), 7.17-7.09 (2H, m), 7.07-6.99 (2H, m), 5.08 (1H, m), 4.60 (1H, m), 4.02-3.18 (4H, m), 2.11-1.84 (2H, m), 1.76-1.44 (5H, m), 0.96 and 0.92 (6H, d, J=6.6 Hz). IR (KBr) cm-1: 2955, 1685, 1640, 1505, 1205. MS (ESI, m/z): 481 (M+H)+. HRMS (ESI, m/z): 481.2268 (Calcd for C26H30FN4O4: 481.2251).
The synthetic route of 1204-75-7 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Daiichi Sankyo Company, Limited; EP2258697; (2010); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider