Heterocyclic Building Blocks-quinoxaline

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.,50998-17-9

To a solution of 11e (70.0 mg, 296 mumol), 6-bromoquinoxaline (94.1 mg, 450 mumol), Bu4NOAc (181 mg, 600 mol) and Pd(OAc)2 (10.1 mg, 45.0 mol) in NMP (0.6 mL). The reaction mixture was stirred for 23 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure. Diluted with water and extracted with EtOAc (3 ¡Á 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12d (15 mg, 14%) as a yellow solid. TLC: Rf 0.2 (1:1 hexane/EtOAc). mp: 208-210 oC. 1H-NMR (400 MHz, CDCl3) delta 8.89 (d, 1H, J = 1.6Hz), 8.85 (d, 1H, J = 1.6 Hz), 8.12 (d, 1H, J = 8.4 Hz), 8.07 (d, 1H, J = 1.6 Hz), 7.76 (dd, 1H, J = 8.4 Hz, J = 2.0 Hz), 7.73 (t, 1H, J = 7.6 Hz), 7.64 (d, 1H, J = 7.6 Hz), 7.59-7.57 (m, 2H), 7.30-7.27 (m, 3H), 7.12 (d, 1H, J = 7.6 Hz), 2.18 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 158.3, 149.1, 146.2, 145.9, 145.8, 143.0, 142.7, 139.1, 132.6, 132.4, 131.6, 131.0, 130.4, 129.5, 128.8, 128.4, 127.8, 123.7, 115.7, 23.8. HRMS (ESI) calcd. for C22H17N6 (M+H): 365.1509; found 365.1512.

50998-17-9 6-Bromoquinoxaline 610939, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Li, Fei; Park, Yunjeong; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry Letters; vol. 23; 4; (2013); p. 1083 – 1086;,
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7467-91-6, Quinoxalin-6-ol is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Underargon, to a solution of 6-ethoxyquinoxaline2(0.29 g, 1.65 mmol) in toluene (20 mL) was added aluminium chloride (0.80 g,5.96 mmol), and the reaction mixture was stirred at 100¡ãC. After 17 h, thereaction mixture was cooled to room temperature, and diluted with 1M aqueousNaOH solution (15 mL) and water (20 mL). The solution was extracted with ethylacetate (60 mL) twice, and the combined organic extracts were washed withbrine, dried over anhydrous Na2SO4, filteredand evaporated under reduced pressure to afford the crude product of 6-hydroxyquinoxalineas a brown oil. This crude product was dissolved in acetone (8.2 mL), and tothe solution were added potassium carbonate (1.14 g, 8.24 mmol) and tert-butylbromoacetate (0.24 mL, 1.64 mmol) at room temperature. The reaction mixture wasstirred at 55¡ãC. After 9 h, the reaction mixture was filtered and washed withacetone. The filtrate was evaporated under reduced pressure, diluted withchloroform, washed with water and brine, dried over anhydrous Na2SO4,filtered and evaporated under reduced pressure. The crude product was purifiedby column chromatography (kanto60N, hexane / ethyl acetate, 5 / 1 to 3 / 1)to afford the tert-butyl ester of the titlecompound as a brown solid (0.22 g, 51percent for 2steps). This ester (0.21 g, 0.83 mmol) was added to 35percent aqueous HCl solution(12 mL), and the reaction mixture was stirred at room temperature. After 7 h,the reaction mixture was evaporated under reduced pressure, and the residue waswashed with diethyl ether to afford the title compound as a brown powder (0.18g, 79percent), 7467-91-6

The synthetic route of 7467-91-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Koda, Hironori; Brazier, John Alan; Onishi, Ippei; Sasaki, Shigeki; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4583 – 4590;,
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6925-00-4,6925-00-4, Quinoxaline-6-carboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of quinoxaline-6-carboxylic acid (2 g, 11.49 mmol) and thionyl chloride (30 mL) was stirred at reflux for 2 hours. The reaction mixture was concentrated to dryness using a rotary evaporator to afford quinoxaline-6- EPO carboxylic acid chloride (crude quantitative). A solution of the above acid chloride (11.49 mmol) in DCM (50 mL) and pyridine (20 mL) was mixed with N,O-dimethyl hydroxylamine HCI salt (2.24 g, 23 mmol) and stirred at room temperature for 12 hours. The reaction was quenched by adding aqueous HCI (50 mL, 1 N), extracted with DCM (3×100 mL), concentrated using a rotary evaporator. The residue was further purified by column (Sitheta2, Hexanes/EtOAc = 1 :3) to yield quinoxaline-6-carboxylic acid methoxy-methyl-amide (2 g, 80%). To a solution of the above Weinreb amide (2.0 g, 9.2 mmol) in THF (30 mL) at O0C was added methyl magnesium bromide (3.9 mL, 11.6 mmol). The reaction mixture was stirred at O0C for 2 hours and then 1 hour at room temperature, quenched by adding aqueous HCI (20 mL, 1 N), extracted with DCM (3×100 mL), concentrated using a rotary evaporator. The residue was further-purified by column (SiO2, Hexanes/EtOAc = 1 :3) to yield 6-acetylquinoxaline (1.17 g, 74%). A solution of 2- chloronicotinic acid ethyl ester (5.0 g, 27 mmol) in MeOH (25 mL) was mixed with sodium methoxide (25.6 mL, 112.5 mmol) and stirred at reflux for 12 hours. The reaction was quenched by adding water (100 mL), extracted with DCM (3×100 mL), concentrated using a rotary evaporator to afford 2-methoxynicotinic acid methyl ester (3.2 g, 71%). A solution of 6-acetylquinoxaline (0.62 g, 3.6 mmol), 2- methoxynicotinic acid methyl ester (0.64 g, 3.8 mmol), and sodium hydride (0.46 g, 11.4 mmol) in THF (100 mL) was stirred at room temperature for 16 hours. The reaction was quenched by adding water (100 mL) and AcOH (20 mL), extracted with dichloromethane (3×100 mL), and concentrated using a rotary evaporator. The residue was re-dissolved in DCM (5 mL) and MeOH (3 mL) and was diluted with Hexanes (50 mL). The solid was removed by filtration and the filtrate was concentrated to afford the diketo compound (0.7 g, 60%). A solution of the above diketone (0.4 g, 1.3 mmol) in AcOH (50 mL) and sulfuric acid (cone, 15 drops) was stirred at reflux for 1 hour. Most of the solvent was removed using a rotary evaporator. The residue was re-dissolved in MeOH and neutralized with potassium carbonate to pH = 8. The solid residue was removed by filtration, washed with MeOH and DCM. The filtrate was extracted with CH2CI2 (3×100 mL) and concentrated using a rotary evaporator. The solid residue was purified by column (SiO2, Hexanes/EtOAc/MeOH = 2:2:1) to afford 2-(quinoxalin-6-yl)-4H- EPO pyrano[2,3-b]pyridin-4-one (90 mg, 24%); MS (ES) m/z: 276 (M+1 ); MP 272.3- 274.80C

As the paragraph descriping shows that 6925-00-4 is playing an increasingly important role.

Reference£º
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
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76982-23-5, 5-Bromoquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

76982-23-5, 5-Bromoquinoxaline (300 mg, 1.44 mmol) and di-tert-butyl hydrazine-1,2-dicarboxylate (500 mg, 2.15 mmol) were dissolved in DMF (5 mL). CuI (27.5 mg, 0.14 mmol) and K3PO4 (609.3 mg, 2.87 mmol) were added and purged with N2, cyclohexane-1,3-diamine (32.8 mg, 0.29 mmol) was added and the reaction mixture was stirred at 110 C. for 16 h. The reaction mixture was filtered through a pad of diatomaceous earth and the pad was washed with EtOAc (20 mL*3). The filtrate was concentrated under reduced pressure to afford a crude produce as a brown oil. The crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate=100:0 to petroleum ether/ethyl acetate=50:50), and the solvents were removed under reduced pressure to afford compound 66a as a brown oil (0.3 g, 58%). LCMS (ESI): m/z 383.0 [M+H]+.

76982-23-5 5-Bromoquinoxaline 610437, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
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879-65-2,879-65-2, 2-Quinoxalinecarboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[1499] to a solution of quinoxaline-2-carboxylic acid (6 g, 34.45 mmol) in MeOH (80 ml) was added con. H2SO4 (675.8 mg, 6.89 mmol) dropwise, then the mixture was stirred at 65 ¡ãC for 10 hours. After cooling to room temperature, the mixture was neutralized with a sat. NaHCO3 and extracted with DCM (60 ml x 3). The organic phases were combined, dried with anhydrous Na2SO4, and evaporated to afford compound 356a (5.80 g, yield: 89.47percent) as a brown solid. The crude product was used directly in the next step without further purification. 1H NMR (CDCl3, 400 mhz) delta 9.56 (s, 1h), 8.31 (d, j = 7.6 hz, 1h), 8.20 (d, j = 8.0 hz, 1h), 7.97 – 7.84 (m, 2h), 4.13 (s, 3h).

As the paragraph descriping shows that 879-65-2 is playing an increasingly important role.

Reference£º
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.80636-30-2,3,3-Dimethyl-3,4-dihydroquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.,80636-30-2

3,4-Dihydro-1,3,3-trimethylquinoxalin-2(1H)-one. In a 200-mL r.b. flask, a solution of 3,4-dihydro-3,3-dimethylquinoxalin-2(1H)-one (1.00 g, 5.66 mmol) in dry THF was treated with NaH (0.28 g, 7.09 mmol, 1.25 equiv). The reaction mixture was stirred at room temperature for 30 minutes before iodomethane (0.39 mL, 6.24 mmol, 1.1 equiv) was added to the reaction flask. The reaction was then stirred at room temperature overnight then partitioned between EtOAc (100 mL) and H2O (20 mL). The aqueous layer was extracted with EtOAc (2*30 mL). The combined organic layers were then washed with brine (20 mL), dried (MgSO4), filtered, and concentrated to a thick oil. Purification by flash chromatography (25% EtOAc/hexane) afforded 830 mg (78%) of 3,4-dihydro-1,3,3-trimethylquinoxalin-2(1H)-one as a white solid. Data for 3,4-dihydro-1,3,3-trimethylquinoxalin-2(1H)-one: 1H NMR (400 MHz, CDCl3) delta 6.90 (m, 3H), 6.67 (d, J=7.7, 1H), 3.69 (bs, 1H), 3.36 (s, 3H), 1.37 (s, 6H).

80636-30-2 3,3-Dimethyl-3,4-dihydroquinoxalin-2(1H)-one 595203, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Ligand Pharmaceuticals, Inc.; US6462038; (2002); B1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6298-37-9,Quinoxalin-6-amine,as a common compound, the synthetic route is as follows.

HATU (0.631 g, 1.66 mmol) was added to a mixture of Intermediate 125 (0.50 g, 1.5 mmol) and quinoxalin-6-amine (0.219 g, 1.51 mmol) in DMF (10 mL) and DIPEA (0.53 mL, 3 mmol) and the reaction mixture was stirred at rt for 16 h. The reaction mixture was partitioned between aq NaHCC -NaCl (30 mL) and EtOAc (2 x 50 mL) and the combined organic components were dried, filtered concentrated and then purified by flash silica chromatography: (40g SiC , eluted with solv A = Hexane / solv B = EtOAc, gradient from 0 – 70%B, hold at 70%B) to yield the title compound (790 mg) as light yellow solid. LC-MS retention time = 1.15 min; m/z = 459.1 [M+H]+. (Column: Waters Aquit BEH C18 2.1 X 50 mm 1.7U. Solvent A = 100% Water: 0.05% TFA. Solvent B = 100% Acetonitrile: 0.05% TFA. Flow Rate = 0.8 mL/min. Gradient: 2-98% B. Gradient Time = 1.5 min. Wavelength = 220)., 6298-37-9

The synthetic route of 6298-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3476-89-9,1,2,3,4-Tetrahydroquinoxaline,as a common compound, the synthetic route is as follows.

Example 4: Synthesis of 2- (3, 4-DIHYDRO-2H-QUINOXALIN-1-YLMETHYL)-1, 1, 1-TRIFLUORO-4- (5- fluoro-2-methoxyphenyl)-4-methylpentan-2-ol A solution of 2-[2-(5-FLUORO-2-METHOXYPHENYL)-2-METHYLPROPYL]-2-TRIFLUOROMETHYLOXIRANE (see Example 1) (54.4 mg) and tetrahydroquinoxaline (124. 8 mg) in DMF (0.6 mL) was heated at 100C for 6 hours. The resulting mixture was diluted with diethyl ether, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 25% diethyl ether-benzene) to give the title compound as a clear oil (31.2 mg)., 3476-89-9

The synthetic route of 3476-89-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/63163; (2004); A1;,
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3476-89-9, 1,2,3,4-Tetrahydroquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Bromine was added dropwise to a magnetically stirred refluxing solution of quinoxaline (1) or tetrahydroquinoxaline 15 or 19 in the relevant solvent. The resulting reaction mixture was heated at reflux temperature. The reaction was monitored by TLC or 1H NMR spectroscopy. After the desired time, the resulting reaction mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The mixture was diluted with a saturated solution of sodium carbonate (10mL) and the mixture was extracted with ethyl acetate (2¡Á25mL). Combined organic layers were washed with water, dried over Na2SO4 and concentrated. The crude was purified appropriate method described in below., 3476-89-9

The synthetic route of 3476-89-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ucar, Sefa; E?siz, Selcuk; Da?tan, Arif; Tetrahedron; vol. 73; 12; (2017); p. 1618 – 1632;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.879-65-2,2-Quinoxalinecarboxylic acid,as a common compound, the synthetic route is as follows.

879-65-2, General procedure: The mixture of ethyl 3,4-diaminobenzoate 19 (1 eq., 7.34 mmol) and appropriate benzoic acid (1 eq., 7.34 mmol) was put under argon atmosphere and 15 mL of POCl3 were added. The whole was heated at reflux for 3 h. The mixture was cooled to room temperature, poured on ice and neutralized with 6 M NaOH (80 mL), then brought to pH ca. 9 by addition of 20 g of solid NaHCO3. 100 mL of CHCl3 were added and phases were separated. Aqueous phase was extracted with CHCl3 (2¡Á50 mL). Combined organic phases were purified by chromatography on silica gel (CHCl3/MeOH, gradient 0-5 %).

The synthetic route of 879-65-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Moszczy?ski-P?tkowski, Rafa?; Majer, Jakub; Borkowska, Ma?gorzata; Bojarski, ?ukasz; Janowska, Sylwia; Mat?oka, Miko?aj; Stefaniak, Filip; Smuga, Damian; Bazyd?o, Katarzyna; Dubiel, Krzysztof; Wieczorek, Maciej; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 96 – 116;,
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