Heterocyclic Building Blocks-quinoxaline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6639-87-8,6-Nitroquinoxaline,as a common compound, the synthetic route is as follows.

Synthesis of 3-chloro-2-methvl-N-auinoxalin-6-vl-benzenesulfonamide, STX 957:; 6-aminoquinoxaline (KRB01083) :; To a solution of 6-nitroquinoxaline [24] (500 mg, 2.86 mmol) in methanol (20 mL) was added 10% palladium on carbon (50 mg) and the mixture was stirred under 1 atm H2 for 4 h. The mixture was filtered through celite and the filtrate evaporated. The residue was passed through a silica plug and evaporated to afford 6-aminoquinoxaline as a yellow solid (342 mg, 82%), single spot at Rf 0.32 (ethyl acetate).’H NMR (CDCI3) : 8 8.65 (1H, d, J= 1.7 Hz), 8.55 (1H, d, J=1.7 Hz), 7.87 (1H, d, J=8. 9 Hz), 7.18 (1H, dd, J=8.9, 2.5 Hz), 7.13 (1H, d, J=2.5 Hz), 4.20 (2H, br. s,-NH2) [25].

As the paragraph descriping shows that 6639-87-8 is playing an increasingly important role.

Reference£º
Patent; STERIX LIMITED; WO2005/42513; (2005); A1;,
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6344-72-5, 6-Methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Methylquinaxoline (100 g, 0.69 mol) was heated in a sealed tube to 160 0C and was then added selenium dioxide (100 g, 0.90 mol). The sealed tube was then stirred at 160 0C for 3 days, then allowed to cool to room temperature. The contents solidified and were dissolved in dichloromethane. Solids were filtered through a celite/silica gel cake. The cake was washed with dichloromethane and washes were combined and concentrated to give a pinkish solid, which was washed with hexane and then dried under vacuum to give quinoxaline-6- carbaldehyde as a white solid (50.5 g, contained ca. 10% of 6-methylquinaxoline).

The synthetic route of 6344-72-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOGEN IDEC MA INC; WO2006/26305; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.148231-12-3,5,8-Dibromoquinoxaline,as a common compound, the synthetic route is as follows.

General procedure: A mixture of 5,8-dibromoquinoxaline (3) (287 mg, 1.0 mmol), Pd(PPh3)2Cl2 (70 mg, 0.1 mmol), CuI (9.5 mg, 0.05 mmol) and PPh3 (26 mg, 0.1 mmol) in triethylamine/tetrahydrofuran 1:1 (20 mL) was stirred and heating until 70 Article; Aguiar, Leonardo de O.; Junior, Adalberto S.L.; Bechtold, Ivan H.; Curcio, Sergio Fernando; Cazati, Thiago; Alves, Tiago V.; Vieira, Andre Alexandre; Journal of Molecular Liquids; vol. 296; (2019);,
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1204-75-7, 3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 4: A suspension of 3-hydroxy-2-quinoxaline carboxylic acid 6-1 (500 mg, 2.63 mmol) and thionyl chloride (2.3 mL, 31.6 mmol, 12.0 equiv) in 10 mL toluene was heated to 80 C. After 2 h of heating, the reaction mixture was cooled to room temperature and evaporated to dryness to yield the acid chloride 7-6. In a separate flask, piperidine 7-5 (0.55 g, 2.63 mmol) and triethylamine (0.73 mL, 5.26 mmol, 2.0 equiv) in 10 mL CH2Cl2 was cooled to 0 C. To this mixture was added the acid chloride 7-6 dropwise. The reaction was allowed to stir at room temperature for 3 h after which was diluted with H2O (10 mL), extracted with EtOAc (2¡Á10 mL), washed with sat. NaHCO3, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography (10-30% EtOAc/CH2Cl2) to produce 7-7 (R isomer).

As the paragraph descriping shows that 1204-75-7 is playing an increasingly important role.

Reference£º
Patent; CHENG, CLIFFORD; SHIPPS, JR., GERALD W.; HUANG, XIAOHUA; HUANG, YING; SHAO, NING; RAO, ASHWIN; PALANI, ANANDAN; ORTH, PETER; VOIGT, JOHANNES H.; HERR, ROBERT J.; ROSSITER, LANA MICHELE; ZENG, QI; SUN, XIANFENG; US2012/122837; (2012); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2427-71-6,6-Chloro-2(1H)-quinoxalinone,as a common compound, the synthetic route is as follows.

EXAMPLE 4 6-Chloro-1,2,3,4-tetrahydroquinoxalin-2-one (IV) Sodium borohydride (5.10 g) is added to a mixture of 6-chloro-1,2-dihydroquinoxalin-2-one (5.60 g), and ethanol (200 ml). The resultant solution is stirred for 2.5 hr at 20-25. The material is partitioned between water and ethyl acetate, the phases are separated, the organic phase is dried over magnesium sulfate and concentrated under reduced pressure to give a solid which is recrystallized from ethyl acetate/hexane to give the title compound, mp 171-174; IR (mineral oil) 2953, 2925, 1687, 1517, 1408, 1307 and 1299 cm-1; NMR (CDCl3 -MeOD) 6.6-6.8 and 3.95 delta; MS (m/z) 182, 153.

As the paragraph descriping shows that 2427-71-6 is playing an increasingly important role.

Reference£º
Patent; The Upjohn Company; US5541324; (1996); A;,
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82031-32-1, 7-Bromoquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7-Bromoquinoxalin-2(lH)-one (313.1 mg, 1.391 mmol) was dissolved in 0.15M DMF (9.2 mL) and treated with potassium carbonate (288.4 mg, 2.087 mmol) and iodomethane (95.5 iL, 1.530 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was then diluted with water and extracted with EtOAc (2 X). The organics were washed with water (3 X) and brine (1 X), dried over Na2S04, filtered and concentrated. Biotage chromatography (hexanes/EtOAc) provided 7- bromo-2-methoxyquinoxaline (25.2 mg, 0.105 mmol, 7.6% yield). 1H NMR (400 MHz, (CD3)2SO) delta = 8.642 (s, 1H), 8.070-8.064 (d, 1H), 7.971-7.950 (d, 1H), 7.801-7.774 (dd, 1H), 4.045 (s, 3H).

The synthetic route of 82031-32-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MATHIEU, Simon; MORENO, David; REN, Li; RUDOLPH, Joachim; WENGLOWSKY, Steven Mark; WO2012/118492; (2012); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.98416-72-9,6-Bromo-2-chloro-3-methylquinoxaline,as a common compound, the synthetic route is as follows.

INTERMEDIATE: (6-Bromo-3-methyl-quinoxalin-2-yl)-hydrazine (IIo). 4-Bromo-2-fluoro-l- nitro-benzene (40 g), racemic alanine (16.2 g), and K2CO3 (30 g) were refluxed overnight in a mixture of in ethanol (200 mL) and water (200 mL). After cooling to ambient temperature, the mixture was diluted with water, and acidified with 1M aq HCl. The precipitated solid was collected and dried to afford 2-(5-bromo-2-nitro-phenylamino)-propionic acid (41 g). A larger portion of this material prepared in a similar manner (60 g) was dissolved in methanol (250 mL) and treated with SOCI2 (30 mL, added drop-wise). The reaction mixture was stirred at ambient temperature overnight. The volatiles were removed in vacuo. The residue was partitioned between EtOAc and aq NaHC03. The organic layer was dried over MgSO i, filtered, and concentrated in vacuo to afford (5- bromo-2-nitro-phenylamino)-propionic acid methyl ester (60 g). This material was dissolved in AcOH (400 mL), iron powder (55 g) was added, and the mixture was refluxed for 4h. After cooling to ambient temperature, the solid was filtered off and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc and sat. aq NaHC03. The organic layer was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica (eluent: heptanes? EtOAc) to afford 6-bromo-3-methyl-3,4-dihydro-lH-quinoxalin-2-one (47.7 g) as a pale yellow solid. A portion of this material (10 g) was dissolved in THF (150 mL), and the solution was cooled on an ice/water bath. Mn02 (19.3 g) was added. The resulting mixture was stirred at ambient temperature overnight. EtOAc (100 mL) was added to the mixture. The solid was filtered off. The filtrate was concentrated in vacuo to afford 6-bromo-3-methyl-lH-quinoxalin-2-one (8.8 g). A larger portion of this material prepared in a similar manner (10 g) was stirred in PI1POCI2 (80 mL) at 150C for 3h. After cooling to ambient temperature, water was added and pH was adjusted to 7 with aqueous ammonia. The precipitated solid was filtered off, washed with water and dried to afford 6-bromo-2-chloro-3-methyl-quinoxaline (6.67 g). A larger portion of this material prepared in a similar manner (14 g) was dissolved in ethanol (250 mL) and hydrazine hydrate (180 mL) was added. The mixture was refluxed for 3h, cooled to ambient temperature, and most of the volatiles were removed in vacuo. The residue was diluted with water, and solid was filtered off, washed with water, and dried to afford IIo (11.2 g) as a yellow solid sufficiently pure for the next step.

98416-72-9 6-Bromo-2-chloro-3-methylquinoxaline 13487186, aquinoxaline compound, is more and more widely used in various.

Reference£º
Patent; H. LUNDBECK A/S; J?RGENSEN, Morten; BRUUN, Anne, Techau; RASMUSSEN, Lars, Kyhn; LARSEN, Mogens; WO2013/34755; (2013); A1;,
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50998-17-9, 6-Bromoquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 6-bromoquinoxaline (0.40 g, 1.9 mmol), 2-propen-l-ol (0.260 mL, 3.8 mmol), tris(dibenzylideneacetone)dipalladium (26 mg, 0.029 mmol), tri-tert-butylphosphonium tetrafluoroborate (16 mg, 0.057 mmol) and N-cyclohexyl-N-methyl-cyclohexanamine (0.49 mL, 2.3 mmol) in 1,4-dioxane (3.0 mL) was stirred at 40 0C overnight. After cooling to RT, the mixture was filtered, washed with methylene chloride and the filtrate was concentrated. The crude material was purified by chromatography on silica gel with EtOAc in Hexane (0-40%) to afford the desired product (195 mg). LCMS: (M+H) = 187.3.

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

Reference£º
Patent; INCYTE CORPORATION; ZHUO, Jincong; METCALF, Brian; WO2008/64157; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23088-23-5,Methyl 6-Quinoxalinecarboxylate,as a common compound, the synthetic route is as follows.

Preparation Example I-1. Quinoxaline-6-carboxylic acid To a solution of quinoxaline-6-carboxylic acid methyl ester (2084mg, 11.07mmol) in ethanol (25mL) was added an aqueous solution of 1 N sodium hydroxide (25mL), and the solution was stirred for 4 hours under reflux. 1 N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, then, the precipitated solid was collected by filtration, washed with water and isopropanol, then dried to obtain the title compound (1477mg, 8.479mmol, 76.6%) as a solid. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 8.18 (1 H, d, J=8.4Hz), 8.29 (1H, dd, J=8.4, 1.2Hz), 8.61 (1 H, d, J=1.2Hz), 9.00-9.07 (2H, m).

23088-23-5 Methyl 6-Quinoxalinecarboxylate 2781239, aquinoxaline compound, is more and more widely used in various.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (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.55686-94-7,2-Chloro-7-nitroquinoxaline,as a common compound, the synthetic route is as follows.

To a suspension of nitro compound VI (14.36 g,68.5 mmol, 1 equiv.) in AcOEt (300 mE) is added SnCl2.2H20 (45.5 g, 239.9 mmol, 3.5 equiv.), then the reaction mixture is refluxed for 2 h. Afier cooling, 50% NaOH (6 equiv., 480 mmol) is added slowly at 00 C. and the reaction mixture is filtered on a silica gel pad and then eluted with hot acetone. After concentration, the residue is purified by recrystallisation with CHC13/petroleum ether to afford compound Had in the form of a yellow solid (9.65 g, 78%). ?H NMR (300 MHz, CDC13) oe ppm: 4.30 (brs, 2H), 7.03 (d, J=1.7 Hz, 1H), 7.15 (dd, J=8.8, 1.7 Hz, 1H), 7.85 (d, J=8.8 Hz, 1H), 8.47 (s, 1H). ?3C NMR (75 MHz, CDC13) oe ppm:107.2, 121.7, 130.3, 135.98, 140.3, 144.2, 147.7, 149.1. High-resolution mass (ESI): mlz calculated for [M+H] C8H7N3C1: 180.0329; mlz measured: 180.0326.

As the paragraph descriping shows that 55686-94-7 is playing an increasingly important role.

Reference£º
Patent; Institut Du Cerveau et de la Moelle Epiniere; Centre National de la Recherche Scientifique (CNRS (CNRS); Sorbonne Universite; Assistance Publique-Hopitaux de Paris; Institut National de la Sante et de la Recherche Medicale (INSERM); Universite Paris-SUD; Figadere, Bruno; Ferrie, Laurent; Le Douaron, Gael; Raisman-Vozari, Rita; Michel, Patrick; Sepulveda, Julia; (18 pag.)US2019/71438; (2019); A1;,
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