Heterocyclic Building Blocks-quinoxaline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6924-66-9,Quinoxaline-5-carboxylic acid,as a common compound, the synthetic route is as follows.

PyBOP (206 mg, 396 muiotaetaomicronIota) was added to a mixture of 8-amino-2-(2-chloro-4-fluorophenyl)-2- azaspiro[4.5]decan-1 -one (isomer 1 ) (100 mg, 330 muiotaetaomicronIota, Intermediate 112), quinoxaline-5- carboxylic acid (71 .9 mg, 413 muiotaetaomicronIota) and N,N-diisopropylethylamine (290 muIota, 1 .7 mmol) in DMF (3.7 ml) and the mixture was stirred over night at room temperature. For work-up, the reaction mixture was concentrated and the residue was purified by preparative HPLC to give the title compound 65.0 mg (43 % yield).LC-MS (Method 1 ): Rt= 1 .14 min; MS (ESIpos): m/z = 453 [M+H]+ 1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 9.78 (d, 1 H), 9.10-9.06 (m, 2H), 8.44 (dd, 1 H), 8.27 (dd, 1 H), 7.98 (dd, 1 H), 7.62-7.58 (m, 1 H), 7.49 (dd, 1 H), 7.35-7.28 (m, 1 H), 3.96-3.85 (m, 1 H), 3.66-3.60 (m, 2H), 2.16 (t, 2H), 2.09-2.00 (m, 2H), 1 .76-1 .66 (m, 4H), 1.60-1 .38 (m, 2H)

The synthetic route of 6924-66-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
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53967-21-8, 6-(Bromomethyl)quinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 6-(bromomethyl)quinoxaline (3 g, 13.5 mmol) and NaN3 (1.2 g, 18.5 mmol) in DMF (50 mL) was stirred at RT for 12h. The reaction was diluted with H2O (500 mL) and extracted with EtOAc (70 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give 6-(azidomethyl)quinoxaline as a yellow solid which was used in the next step without further purification. (2.5 g crude). ESI-MS [M+H]+: 186.2.

53967-21-8 6-(Bromomethyl)quinoxaline 10214510, aquinoxaline compound, is more and more widely used in various.

Reference£º
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
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34117-90-3, 3-Chloroquinoxalin-2-amine is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Heating a mixture of 2a (495 mg, 2.75 mmol) and Ph2PH (0.48 mL, 2.76 mmol) in the presence of Pd(OAc)2 (0.8 mg, 0.13 mol%) for 2 h at 130C led to a viscous blue-green mass. Extraction of the soluble part with diethyl ether and NMR monitoring in C6D6 identified Ph2P-PPh2, Ph2PCl, 3a and an unknown phosphorus compound (31P signals at d 14.9, 82.2, 12.8 and 5.4 ppm, intensity ratio 84:12:2:2). The insoluble hydrochloride part, 615 mg blue-green powder, was treated with aqueous NaOH/Et2O. The ether phase was dried with Na2SO4 and the ether removed in vacuo to give a brownish-yellow viscous mass (220 mg) with a low content of 3a (relative 31P intensity ca. 20% besides signals of Ph4P2, Ph2PHO and other P compounds). Purification under aerobic conditions by column chromatography on silica gel (ethyl acetate/hexane 95/5%) and removal of solvent gave 180 mg (45%) pale yellow solid 2-aminoquinoxaline. Mp: 156C. 1H NMR (CDCl3) d: 5.03 (vbr s, 2H, NH2), 7.45 (td, 3J = 8.4, 7, 4J = 1.2 Hz, 1H, H-6), 7.61 (td, 3J = 8.4, 7, 4J = 1.2 Hz, 1H, H-7), 7.67 (dd, 3J = 8.4, 4J = 1.2 Hz, 1H, H-8), 7.92 (dd, 3J = 8.4, 4J = 1.2 Hz, 1H, H-5), 8.35 (s, 1H, H-3); these values are in good agreement with the reported data [17]. 13C NMR (CDCl3) d: 125.05 (CH-6), 125.88 (CH-8), 128.83 (CH-5), 137.43 (Cq-4a), 137.78 (CH-3), 130.29 (CH-7), 140.89 (Cq-8a), 151.97 (Cq-2). HRMS (ESI in MeOH): Calc. for C8H7N3 [M+H+] 146.0713; found: 146.0713.

34117-90-3 3-Chloroquinoxalin-2-amine 817274, aquinoxaline compound, is more and more widely used in various.

Reference£º
Article; Adam, Mohamed Shaker S.; Mohamad, Ahmad Desoky; Jones, Peter G.; Kindermann, Markus K.; Heinicke, Joachim W.; Polyhedron; vol. 50; 1; (2013); p. 101 – 111;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of N,N’-carbonyldiimidazole (363 mg) and triethylamine (312 mul) in chloroform (10 ml), E-4-aminoadamantan-1-ol obtained in Reference Example 2 (250 mg) and N,N-dimethylformamide (4 ml) were added and stirred at room temperature for 1 hour. To the reaction mixture, tert-butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate obtained in Reference Example 28 (698 mg) was added and heated under reflux for 6 hours, followed by stirring overnight at room temperature. The reaction mixture was then heated under reflux for an additional 8 hours. After cooling at room temperature, the reaction mixture was diluted with water and extracted with chloroform. The organic layer was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and washed sequentially with 0.1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluding solvent: n-hexane:ethyl acetate = 5:1 to 1:1 ? chloroform:methanol = 9:1) to give the titled compound (Compound 31, 290 mg) as a colorless amorphous substance. 1H NMR (300 MHz, CHLOROFORM-D) delta 1.35 (s, 1 H), 1.43-1.61 (m, 13 H), 1.70-1.79 (m, 4 H), 1.84-1.93 (m, 2 H), 2.06-2.19 (m, 3 H), 3.80-3.86 (m, 4 H), 3.89-3.97 (m, 1 H), 5.38 (d, J=6.5 Hz, 1 H), 7.04-7.20 (m, 2 H), 7.28-7.33 (m, 1 H), 8.00-8.05 (m, 1 H).

887590-25-2 tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate 16740533, aquinoxaline compound, is more and more widely used in various.

Reference£º
Patent; Taisho Pharmaceutical Co. Ltd.; EP2172453; (2010); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.50998-17-9,6-Bromoquinoxaline,as a common compound, the synthetic route is as follows.

EXAMPLE 1276-[3-(lH-Pyrazol-l-yl)phenyl]quinoxaline6-Bromoquinoxaline (100 mg, 0.48 mmol), 3-(lH-pyrazol-l-yl)phenylboronic acid (108 mg, 0.57 mmol), Na2CO3 (0.15 g, 1.44 mmol), Pd(PPh3)4 (55 mg, 0.048 mmol), water (2 mL) and DME (6 mL) were combined in a sealed tube and heated under microwave irradiation to 12O0C for 1 h. The reaction mixture was concentrated to dryness and purified by preparative EtaPLC to give the title compound (62.1 mg, 47%) as a pale yellow solid. deltaEta (CDCl3) 8.89 (IH, d, J 1.84 Hz), 8.86 (IH, d, J 1.84 Hz), 8.38 (IH, d, J2.05 Hz), 8.20 (IH, d, J8.74 Hz), 8.15-8.09 (2H, m), 8.03 (IH, d, J2.51 Hz), 7.78 (IH, d, J 1.76 Hz), 7.75 (IH, ddd, J8.00, 2.25, 1.14 Hz), 7.69-7.66 (IH, m), 7.63-7.55 (IH, m), 6.52 (IH, dd, J2.50, 1.78 Hz). LCMS (ES+) 273 (M+H)+, 15.14 minutes {Method 4).

The synthetic route of 50998-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
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2958-87-4, 2,3,6-Trichloroquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example C 6-Chloro-2,3-dicyanoquinoxaline A mixture of 11.7 g of 2,3,6-trichloroquinoxaline, 5.39 g of sodium cyanide and 2.04 g of benzyltrimethylammonium chloride is stirred in 200 ml of DMSO at room temperature for 24 hours. With intensive stirring the reaction mixture is poured onto 520 ml of ice-water, stirred for an hour, and filtered with suction, and the solid product is washed with water. Drying at 40 C. gives 8.12 g (76% of theory) of a gray powder of a compound with the following formula MS (m/e): 215 [M+H]+, 237 [M+Na]+ H NMR (DMSO): 8.53 (d, 1H), 8.37 (d, 1H), 8.26 (dd,1H)

The synthetic route of 2958-87-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Heckmann, Heino; Metz, Hans Joachim; US2007/264600; (2007); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1593-08-4,2-Formylquinoxaline,as a common compound, the synthetic route is as follows.

General procedure: Two drops of glacial acetic acid as a catalyst were added to themixtures of thiosemicarbazides (0.5 mmol) and di(2-pyridyl) ketone,2-pyridinecarboxaldehyde, 2-quinolinecarboxaldehyde, 8-hydroxy-2-quinolinecarboxaldehyde or 2-quinoxalinecarbaldehyde (0.5 mmol) in ethanol (5 ml). The glasstubes were sealed and placed into a microwave reactor at 83 C for20 min (the reactor power did not exceed 50W). The final productswere crystallized from dry methanol.

As the paragraph descriping shows that 1593-08-4 is playing an increasingly important role.

Reference£º
Article; Mrozek-Wilczkiewicz, Anna; Malarz, Katarzyna; Rejmund, Marta; Polanski, Jaroslaw; Musiol, Robert; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 180 – 194;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6344-72-5,6-Methylquinoxaline,as a common compound, the synthetic route is as follows.

Intermediate 17: 6-(bromomethyl)quinoxaline A mixture of 6-methylquinoxaline (300 mg), NBS (370 mg) and benzoyl peroxide (5.04 mg) in carbon tetrachloride (8 ml.) was heated at reflux under an atmosphere of argon for 18 hr. The reaction mixture was cooled to RT, filtered and concentrated under reduced pressure to give a brown oil. The crude product was purified by column chromatography (Biotage SP4, 40+M column, 20-100% EtOAc / isohexane. The fractions containing product were combined and concentrated under reduced pressure to give the title compound (243 mg) as a white solid, m/z [M+H]+: 223.1 / 225.0. Retention time 0.80 min (LC/MS method 3).

As the paragraph descriping shows that 6344-72-5 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/23753; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6344-72-5,6-Methylquinoxaline,as a common compound, the synthetic route is as follows.

A suspension of 3,4-diaminotoluene (50.0 g; 0.409 mol.) and glyoxal (40% aq. soln.; 52.0 mL; 0.450 mol.) in water (150 mL) and CH3CN (20.0 mL) was heated to 60 0C for 1 h. Heating was then discontinued and brine (100 mL) was added. The solution was extracted with EtOAc (3 x 150 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification via distillation under reduced pressure (1200C, 10 torr) provided 6-methylquinoxaline (48.0 g, 81 %) as a clear, colorless oil. 1 H NMR (400 MHz, CDCl3) delta ppm 2.61 (s, 3 H) 7.61 (dd, J=8.59, 1.77 Hz, 1 H) 7.88 (s, 1 H) 8.00 (d, J=8.59 Hz, 1 H) 8.79 (dd, J=9.85, 1.77 Hz, 2 H) MS(ES+) m/e 145 [M+H]+. A suspension of 6-methylquinoxaline (8.O g; 0.055 mol.) and selenium dioxide (6.77 g; 0.061 mol.) in 1 ,4-dioxane (5.0 mL) was irradiated at 2000C for 30 min. in a Biotage Initiator microwave synthesizer. The above procedure was repeated five further times and the combined, cooled reaction mixtures were dissolved in CH2CI2, filtered through a plug of celite, and concentrated in vacuo. Purification via flash column chromatography (silica gel,20-50% ethyl acetate in hexanes) followed by crystallization from CH2CI2 provided quinoxaline-6-carbaldehyde (40.0 g, 91%) as a white solid. 1H NMR EPO (400 MHz, CDCI3) delta ppm 10.25 (s, 1 H) 8.95 (s, 2 H) 8.57 (d, J=1.3 Hz, 1 H) 8.24 (dd, J=8.6, 1.5 Hz, 1 H) 8.20 (d, J=8.6 Hz, 1 H). MS(ES+) m/e 159 [M+H]+.

6344-72-5 6-Methylquinoxaline 242567, aquinoxaline compound, is more and more widely used in various.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/127458; (2006); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6344-72-5,6-Methylquinoxaline,as a common compound, the synthetic route is as follows.

Intermediate 17: 6-(bromomethyl)quinoxaline A mixture of 6-methylquinoxaline (300 mg), NBS (370 mg) and benzoyl peroxide (5.04 mg) in carbon tetrachloride (8 ml.) was heated at reflux under an atmosphere of argon for 18 hr. The reaction mixture was cooled to RT, filtered and concentrated under reduced pressure to give a brown oil. The crude product was purified by column chromatography (Biotage SP4, 40+M column, 20-100% EtOAc / isohexane. The fractions containing product were combined and concentrated under reduced pressure to give the title compound (243 mg) as a white solid, m/z [M+H]+: 223.1 / 225.0. Retention time 0.80 min (LC/MS method 3).

6344-72-5 6-Methylquinoxaline 242567, aquinoxaline compound, is more and more widely used in various.

Reference£º
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/23753; (2011); A1;,
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