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Trimethylsilyldiazomethane [2.0M in hexanes] (0.08?xL) was added dropwise to a solution of quinoxalin-6-yl-acetic acid (0.030g, 0.159mmol) in toluene/methanol [8/1] (0.5mL) and stirred until the bubbling stopped. The reaction was then evaporated and the crude product was purified via silica gel column chromatography in hexane: ethyl acetate (1:1) to give 0.013g of quinoxaJin-6-yl-acetic acid methyl ester. This was added to a solution of hydrazine (O.lOinL) in methanol and stirred at room temperature overnight. The reaction mixture was evaporated in vacuo to give 0.019g of quinoxalin-6-yl-acetic acid hydrazide. 1H NMR (400 MHz, DMSO-d6) 8 9.77 (bs, IH), 9.35 (m, 2H), 8.46 (d, IH, J=8.8Hz), 8.39 (m, IH), 8.19 (dd, IH, J=2.0, 8.8Hz), 4.68 (bs, 2H), 4.07 (s, 2H).
Trimethylsilyldiazomethane [2.0M in hexanes] (0.08?xL) was added dropwise to a solution of quinoxalin-6-yl-acetic acid (0.030g, 0.159mmol) in toluene/methanol [8/1] (0.5mL) and stirred until the bubbling stopped. The reaction was then evaporated and the crude product was purified via silica gel column chromatography in hexane: ethyl acetate (1:1) to give 0.013g of quinoxaJin-6-yl-acetic acid methyl ester. This was added to a solution of hydrazine (O.lOinL) in methanol and stirred at room temperature overnight. The reaction mixture was evaporated in vacuo to give 0.019g of quinoxalin-6-yl-acetic acid hydrazide. 1H NMR (400 MHz, DMSO-d6) 8 9.77 (bs, IH), 9.35 (m, 2H), 8.46 (d, IH, J=8.8Hz), 8.39 (m, IH), 8.19 (dd, IH, J=2.0, 8.8Hz), 4.68 (bs, 2H), 4.07 (s, 2H).
3-(cyclohex-1-en-1-yl)-7-methoxy-2-phenyl-6-(quinoxalin-6-yl)-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)pyrazolo[1,5-a]pyrimidin-5-amine[ No CAS ]
3-(cyclohex-1-en-1-yl)-2-phenyl-6-(quinoxalin-6-yl)-5-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)pyrazolo[1,5-a]pyrimidin-7(4H)-one[ No CAS ]
To dimethyl carbonate (30 mL) cooled at 0 was added potassium tert-butanolate (3.8 g, 34.12 mmol) in portions. The resultant mixture was stirred at 0 for 1 hour. Methyl 2- (quinoxalin-6-yl) acetate (2.3 g, 11.37 mmol) was added. The resultant mixture was slowly warmed up to room temperature and stirred for 1 hour. The reaction mixture was heated to 90 and stirred for 1.5 hours. After cooling to room temperature, the mixture was diluted with EtOAc (150 mL) , washed with saturated NH4Cl (80 mL) and brine (50 mL) , dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column (petroleum ether/ethyl acetate3: 1) to obtain dimethyl 2- (quinoxalin-6-yl) malonate (2.0 g) as a yellow solid. 1H NMR (CHLOROFORM-d) : delta 8.89 (s, 2H) , 8.10 -8.19 (m, 2H) , 7.91 (dd, J 8.7, 2.0 Hz, 1H) , 4.95 (s, 1H) , 3.82 (s, 6H) . LC-MS: m/z 261.1 (M+H) +.
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