Heterocyclic Building Blocks-quinoxaline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.49679-45-0,Ethyl 3-chloroquinoxaline-2-carboxylate,as a common compound, the synthetic route is as follows.

General procedure: Method A: a solution of compound 3 (1.11 g, 4.70 mmol), 3- aminophenol (622 mg, 5.70 mmol) and p-TSA, as a catalyst, in absolute ethanol (40 mL) was refluxed for 110 h. Ethanol was then evaporated under reduced pressure, and the resulting residue was purified by silica column chromatography using cyclohexane with ethyl acetate gradient (0e50%) as eluent to give the desired compound 4a (1.0 g, 69%) as a red powder.

49679-45-0, The synthetic route of 49679-45-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Oyallon, Bruno; Brachet-Botineau, Marie; Loge, Cedric; Bonnet, Pascal; Souab, Mohamed; Robert, Thomas; Ruchaud, Sandrine; Bach, Stephane; Berthelot, Pascal; Gouilleux, Fabrice; Viaud-Massuard, Marie-Claude; Denevault-Sabourin, Caroline; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 101 – 109;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.32601-86-8,2-Chloro-3-methylquinoxaline,as a common compound, the synthetic route is as follows.

A mixture of 2-chloro-3-methylquinoxaline (500 mg, 2.8 mmol, Oakwood), methyl glycolate (1.06 mL, 14 mmol) and K2CO3 (1.93 g, 14 mmol) in DMF (14 mL) was stirred overnight at 60 C. By morning, the title compound had formed along with the methyl ester in approximately a 3:4, respectively. 1N NaOH (5.6 mL, 5.6 mmol), water (10 mL), and DCM (10 mL) were added and the reaction stirred overnight at room temperature while stirring vigorously. By morning, the product ratio had improved to approximately 1:1. Concentrated hydrochloric acid was added until a pH=3. The layers were separated and the aqueous layer was extracted with DCM twice more. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrate in vacuo. The crude material was purified by prep HPLC. Obtained 305 mg (50% yield) of the title compound as a white powder. 1H NMR (300MHz, CD3OD) delta = 7.93 – 7.86 (m, 1H), 7.82 – 7.75 (m, 1H), 7.69 – 7.53 (m, 2H), 5.10 (s, 2H), 2.67 (s, 3H)Retention time = 3.49 min. LCMS (ESI) m/z 219.02 (M+1)+

32601-86-8, The synthetic route of 32601-86-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Loughran, H. Marie; Han, Ziying; Wrobel, Jay E.; Decker, Sarah E.; Ruthel, Gordon; Freedman, Bruce D.; Harty, Ronald N.; Reitz, Allen B.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3429 – 3435;,
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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

The resulting compound (940 mg, 2.37 mmol) was condensed with 3-hydroxyquinoxaline-2-carboxylic acid (540 mg, 2.84 mmol) to afford the desired title compound (680 mg, yield 54%) as a pale yellow solid. 1H-NMR (DMSO-d6, 400 MHz) delta: 12.83 (1H, brs), 9.55 (1H, brs), 7.86 (1H, m), 7.61 (1H, m), 7.38 (2H, m), 7.28 (1H, m), 7.11 (3H, m), 4.90 (1H, dd, J=7.6 Hz, 7.1 Hz), 4.68 (1H, m), 3.99-3.80 (2H, m), 3.57-3.20 (2H, m), 2.05 (4H, m), 1.68 (1H, m), 0.94 (6H, d, J=6.4 Hz). IR (KBr)cm-1: 2960, 1690, 1640, 1505, 1240, 1160. MS (ESI, m/z): 533 (M+H)+. HRMS (ESI, m/z): 533.1998 (Calcd for C26H25F3N4O5: 533.2012). Anal. Calcd for C26H27F3N4O5: C, 58.64; H, 5.11; N, 10.52. Found: C, 58.28; H, 5.12; N, 10.51., 1204-75-7

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;,
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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 C. Then, the respective terminal arylacetylene (4aeg) (2.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise. The reaction mixture was stirred under reflux for 20min under a nitrogen atmosphere. Cooled down to room temperature, the solution was evaporated, and the crude product was purified by a silica gel chromatography column using hexane/dichloromethane (70:30) as the eluent to afford the respective final compound 5a-g. 5.3.1. 5,8-Bis[(4-methoxyphenyl)ethynyl]quinoxaline: compound 5a Yield: 74 mg (55%). IR (KBr): 2956, 2919, 2850, 2210, 1602, 1565, 1507, 1464, 1248, 826 cm 1.1H NMR (400 MHz, CDCl3) d ppm: 9.00 (s, 2 H), 7.97 (s, 2 H), 7.64 (d, J ? 8.0 Hz, AreH, 4 H), 6.93 (d, J ? 8.0 Hz, AreH, 4 H), 3.85 (s, -OCH3, 6 H). 13C NMR (100 MHz, CDCl3) d ppm: 160.1, 145.4, 143.1, 133.6, 133.4, 123.9, 115.0, 114.0, 97.8, 85.1, 55.3. APPI-MS m/z: Molecular formula C26H18N2O2 requires [MthH]th 391.1441; found: 391.1443., 148231-12-3

The synthetic route of 148231-12-3 has been constantly updated, and we look forward to future research findings.

Reference£º
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

The resulting compound (113 mg, 0.382 mmol) was condensed with 3-hydroxyquinoxaline-2-carboxylic acid (72.7 mg, 0.382 mmol) to afford the desired title compound (92.8 mg, yield 51%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz) delta: 12.67 (1H, brs), 10.17 (1H, brs), 8.05-7.96 (1H, m), 7.70-7.32 (3H, m), 7.04-6.84 (4H, m), 5.08 (1H, dd, J=7.6 Hz, 7.1 Hz), 4.53-4.46 (1H, m), 4.00-3.68 (4H, m), 2.38-2.09 (1H, m), 2.02-1.85 (4H, m), 1.17-1.07 (6H, m). IR (KBr)cm-1: 2960, 1690, 1630, 1505, 1210. MS (ESI, m/z): 467 (M+H)+. HRMS (ESI, m/z): 467.2170 (Calcd for C25H28FN4O4: 467.2095)., 1204-75-7

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;,
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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

3-chloroquinoxalin-2-amine (1.8 g, 10 mmol) and 3, 5 -dimethoxy aniline (4.6 g, 30 mmol, commercially available from Aldrich) are taken up in NMP (4.5 ml) and heated to 1450C in the sealed tube for 3h under N2. When TLC confirms the total consumption of the starting material, the reaction is cooled to rt and treated with EtOAc (4 ml). The first crop of solid is filtered followed by the 2nd crop. The first is recrystallised from CHCl3: EtOAc and the 2nd crop is washed with EtOAc, to afford 1.8 g (60 %) of pure title compound. LC/MS: (ES+): 297.1, (ES-): 295.1.

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

Reference£º
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/23186; (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.

This procedure is based on our previous report27 and vogels procedure36. To a conical flask containing NaOH solution (1.5eq, 10 mL H2O) was added substituted acetophenones (1mmole) in ethanol (10 mL), and the reaction mixture was stirred for 10 minutes to allow enolate formation, to this was added quinoxaline-2- carbaldehyde 1 (1mmole) and the reaction mixture was stirred till completion. After completion of the reaction, as monitored by TLC the reaction mixture was poured in an ice bath and was acidified using conc. HCl. The solid obtained was then filtered, dried and recrystallized using Ethanol. The quinoxalinyl chalcone 2a-n were then characterized using IR, NMR (1H, 13C) and HR-MS spectroscopy. The purity was checked by HPLC measurements using mobile phase consisting methanol and water in the ratio 90:10.

1593-08-4, 1593-08-4 2-Formylquinoxaline 594088, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Desai, Vidya; Desai, Sulaksha; Gaonkar, Sonia Naik; Palyekar, Uddesh; Joshi, Shrinivas D.; Dixit, Sheshagiri K.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 10; (2017); p. 2174 – 2180;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.82019-32-7,7-Bromo-1-methyl-1H-quinoxalin-2-one,as a common compound, the synthetic route is as follows.

82019-32-7, Add the substrate 1-methyl-7-bromoquinoxaline-2(1H)-one to a 15 ml reaction tube 71.7 mg, 0.3 mmol, the substituent on the structural formula R1 is a methyl group, and R2 is a bromine atom), Sodium trifluoromethylsulfinate (CF3SO2Na, 140.5 mg, 0.9 mmol), An oxidizing agent iodobenzene bis(trifluoroacetate) (387.0 mg, 0.9 mmol) was added. The oil pump was evacuated, filled with argon gas, and repeated 3 times, and 3 ml of acetonitrile was added by a syringe. The mixture was stirred at room temperature under an argon atmosphere for 12 hours. The reaction was confirmed to be completely complete by TLC. The solvent acetonitrile was distilled off and then directly purified by column chromatography (ethyl acetate / petroleum ether = 1/3) to give the produc 1-methyl-3-trifluoromethyl-7-bromoquinoxaline-2(1H)-one 49.8 mg, total yield 54%.

As the paragraph descriping shows that 82019-32-7 is playing an increasingly important role.

Reference£º
Patent; Hebei University of Technology; Zhang Hongyu; Wang Liping; Zhang Yuecheng; Zhao Jiquan; (13 pag.)CN108976174; (2018); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2379-60-4,2 3-Dichloro-6-nitroquinoxaline,as a common compound, the synthetic route is as follows.

2379-60-4, A. 3-Chloro-2-methoxy-6-nitroquinoxaline A slurry of 6.1 g (25 mmol) of 2,3-dichloro-6-nitroquinoxaline in 70 ml of dry methanol was heated to 50 C and treated dropwise over 5 h with 0.7 g (30 mmol) of sodium dissolved in 70 ml of dry methanol. The mixture was stirred over night at 50 C., cooled and filtered. The resulting precipitate was washed with cold ethanol and water and finally chromatographed on silica gel with toluene to give 3.5 g (58%) of the title compound; m.p. 155-158 C.; 1 H-NMR (DMSO-d6): delta4.17 (s, 3H, CH3), 8.05 (d,J=9 Hz, 1H, H-8), 8.48 (dd, J7-8 =9 Hz, J7-5 =2 Hz, 1H, H-7), 8.73 (d, J=2 Hz, 1H, H-5).

2379-60-4 2 3-Dichloro-6-nitroquinoxaline 689090, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Novo Nordisk A/S; US5504085; (1996); A;,
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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

Example 138 Preparation of Quinoxaline-2-carboxylic acid {(S)-1-[1-(2-cyano-benzenesulfonyl)-3-oxo-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide Following the procedure of Example 75, except substituting 2-cyanophenylsulfonyl chloride for thiazole-2-sulfonyl chloride and quinoxaline-2-carboxylic acid for benzofuran-2-carboxylic acid, the title compound was prepared. The residue was purified by HPLC. First eluding diastereomer; MS (M+H+): 563.2; 1H-NMR (400 MHz, CDCl3): ¡¤9.65(s, 1H), 8.40(m, 1H), 8.22-8.10(m, 3H), 7.90-7.22(m, 5H), 7.00(d, 1H), 5.10(m, 1H), 4.75(m, 1H), 4.65-4.60(d, 1H), 4.20-4.10(m, 1H), 3.72-3.70(d, 1H), 2.70(m, 1H), 2.38(m, 2H), 1.95-1.40(m, 5H), 1.02(d, 6H); and the second eluding diastereomer: MS (M+H+) 563.2.

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

Reference£º
Patent; SmithKline Beecham Corporation; US2002/147188; (2002); A1;,
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