Heterocyclic Building Blocks-quinoxaline

1865-11-8, Methyl quinoxaline-2-carboxylate is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: In a round bottom flask, the previously prepared methyl ester 2 (2 g, 10.6 mmol) was stirred in ethanol (50 mL) in the presence of cesium carbonate (0.3 g, 0.92 mmol) at ambient temperature. The progress of the reaction was followed by GC chromatography. At the end of the transesterification, the reaction mixture was evaporated to dryness and the product was extracted with dichloromethane (425 mL). The combined organic layers were then dried over MgSO4 and, after filtration, evaporated to dryness. The ethyl ester 3 was obtained as beige powder. Yield: 67percent.

1865-11-8, 1865-11-8 Methyl quinoxaline-2-carboxylate 478049, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Maj, Anna M.; Heyte, Svetlana; Araque, Marcia; Dumeignil, Franck; Paul, Sebastien; Suisse, Isabelle; Agbossou-Niedercorn, Francine; Tetrahedron; vol. 72; 10; (2016); p. 1375 – 1380;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1204-75-7,3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid,as a common compound, the synthetic route is as follows.

The resulting compound (180 mg, 0.470 mmol) was condensed with 3-hydroxyquinoxaline-2-carboxylic acid (90.0 mg, 0.470 mmol) to afford 3-hydroxy-N-[(1S)-2-methyl-1-({4-[(2-methyl-1,3-benzothiazol-6-yl)oxy]piperidin-1-yl}carbonyl)propyl]quinoxaline-2-carboxamide (181 mg, yield 74%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz) delta: 12.78 (1H, brs), 10.20 (1H, brs), 7.99 (1H, s), 7.85 (1H, dd, J=8.8 Hz, 5.9 Hz), 7.61 (1H, brs), 7.51 (1H, brs), 7.34 (2H, dd, J=5.9 Hz, 2.0 Hz), 7.07 (1H, dt, J=9.1 Hz, 2.0 Hz), 5.09 (1H, t, J=7.3 Hz), 4.68-4.61 (1H, m), 4.02-3.73 (4H, m), 2.81 (3H, d, J=2.0 Hz), 2.40-2.17 (2H, m), 2.07-1.91 (3H, m), 1.16-1.09 (6H, m). IR (KBr) cm-1: 2960, 1690, 1640, 1530, 1455, 1210. MS (ESI, m/z): 520 (M+H)+. Anal. Calcd for C27H29N5O4S: C, 62.41; H, 5.63; N, 13.48. Found: C, 62.17; H, 5.79; N, 13.17., 1204-75-7

1204-75-7 3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid 71001, aquinoxaline compound, is more and more widely used in various fields.

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.2958-87-4,2,3,6-Trichloroquinoxaline,as a common compound, the synthetic route is as follows.

EXAMPLE 2 9-Chloro-1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxaline and 10-chloro-1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxaline A mixture of 23.3 g. of 2,3,6-trichloroquinoxaline, 11.5 g. of 2-piperidinomethanol, 40 ml. of triethylamine and 400 ml. of dimethylformamide is stirred at room temperature for 4 hours and then heated on a steam bath for 48 hours. A 500 ml. portion of water is added dropwise. The solid is recovered by filtration, washed with water and air dried. This solid is dissolved in dichloromethane, passed through Magnesol and recrystallized from ethyl acetate. Recrystallization from ethanol or ethyl acetate gives pale yellow crystals of 10-chloro-1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxaline, m.p. 147-149 C. Fractional crystallization from the mother liquor gives a second yield of the above 10-chloro derivative plus 9-chloro-1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxaline, m.p. 107-109 C. The monohydrochloride salts of both compounds may be prepared as described in Example 1 and decompose above 300 C., 2958-87-4

2958-87-4 2,3,6-Trichloroquinoxaline 18070, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; American Cyanamid Company; US4200748; (1980); A;,
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879-65-2, 2-Quinoxalinecarboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

879-65-2, General procedure: To a flask containing amine (1 eq), and carboxylic acid (1.5 eq) in DMF or EtOAc (0.1 M-0.2 M) were added either N-methylimidazole, diisopropylethylamine, or triethylamine (3.0-5.0 eq) followed by T3P solution (1.5-3.0 eq., 50% in EtOAc). The resulting reaction mixture was stirred at rt for 4 h, at which point 1 M NaOH solution was added followed by EtOAc. The layers were separated, and the aqueous layer was extracted with EtOAc (3x). The combined organic layers were dried over anhydrous Mg504, filtered and concentrated under reduced pressure. The cmde reaction mixture was purified employing silica flash chromatography or reverse-phase HPLC to provide the desired product.

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

Reference£º
Patent; DENALI THERAPEUTICS INC.; CRAIG, Robert A., II; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; HALE, Christopher R. H.; LEXA, Katrina W.; OSIPOV, Maksim; REMARCHUCK, Travis; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (187 pag.)WO2019/32743; (2019); 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.

50998-17-9, 6-Bromo quinoxaline (2.0 g, 9.5 mmol) in toluene (20 ml.) was degassed for 30 min. To this solution, 1-ethoxy vinyl tributyltin (3.8 g, 10.5 mmol) and bis(triphenylphosphine)palladium dichloride (0.67 g, 0.95 mmol) were added at rt and stirred for 16 hours at 90 C. The reaction mixture was cooled to rt and filtered through celite. After evaporation of the solvent, 6 N HCl solution in water (20 ml.) was added and the mixture was stirred for 1 hour at rt. It was concentrated and neutralized with sat. NaHCO3. The desired product was extracted with DCM (100 mL,), dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography to afford the title compound (brown solid). 1H NMR (400 MHz, DMSO-d6): delta 9.06-9.04 (m, 2H), 8.70 (d, J=2.4 Hz, 1H), 8.28 (t, J = 2.8 Hz, 1H), 8.16 (d, J = 11.6 Hz, 1H), 2.97 (s, 3H). LCMS: (Method A) 173 (M+H), Rt. 2.25 min, 99.06% (Max).

As the paragraph descriping shows that 50998-17-9 is playing an increasingly important role.

Reference£º
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); A1;,
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6925-00-4, Quinoxaline-6-carboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,6925-00-4

Reference Example I-1. Quinoxaline-6-carboxylic acid 3-phenoxybenzylamide To a solution of quinoxaline-6-carboxylic acid described in Preparation Example I-1 (15mg, 0.063mmol) and 4-phenoxybenzylamine described in Preparation Example 3 (13mg, 0.063mmol) in N,N-dimethylformamide (2mL) were added benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (36mg, 0.069mmol) and triethylamine (19mul, 0.14mmol), which was then stirred at room temperature for 24 hours. The reaction mixture was concentrated, the residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (12mg, 0.025mmol, 40%) was obtained as a trifluoroacetic acid salt. MS m/e(ESI) 356.37(MH+)

The synthetic route of 6925-00-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
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32601-86-8, 2-Chloro-3-methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-chloro-3-methylquinoxaline L [45] (500mg, 2.8mmol) and 4-chlorothiophenol (405mg, 2.8mmol) in anhydrous DMF (10mL), Cs2CO3 (912mg, 2.8mmol) was added under inert atmosphere. The mixture was stirred at 70C overnight. After completion of the reaction, water was added, leading to a precipitate which was separated by filtration. The resulting precipitate was then thoroughly washed with water. The precipitate was dissolved in CH2Cl2 and dried with Na2SO4. After filtration and evaporation, the resulting solid was purified by silica gel column chromatography (eluent: Petroleum Ether/CH2Cl2 1/1) to afford 2-((4-chlorophenyl)thio)-3-methylquinoxaline. Yield 83%. Beige powder. mp 118C. 1H NMR (250MHz, CDCl3) delta=7.96-7.92 (m, 1H), 7.72-7.68 (m, 1H), 7.60-7.54 (m, 4H), 7.44 (d, J=6.6 Hz, 2H), 2.77 (s, 3H). 13C NMR (101MHz, CDCl3) delta=155.3, 151.4, 141.4, 140.0, 136.7, 135.6, 129.5, 129.2, 128.6, 128.3, 128.1, 127.2, 22.4. LC-MS (ESI, 35 eV): tR=5.51min, m/z 287 [M+H]+., 32601-86-8

As the paragraph descriping shows that 32601-86-8 is playing an increasingly important role.

Reference£º
Article; Desroches, Justine; Kieffer, Charline; Primas, Nicolas; Hutter, Sebastien; Gellis, Armand; El-Kashef, Hussein; Rathelot, Pascal; Verhaeghe, Pierre; Azas, Nadine; Vanelle, Patrice; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 68 – 86;,
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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

53967-21-8, Example 25 6-({4-[2-(4-tert-butylphenyl)-1,3-benzoxazol-7-yl]piperazin-1-yl}methyl)quinoxaline: To a suspension of 2-(4-tert-butylphenyl)-7-piperazin-1-yl-1,3-benzooxazole 23.5 mg, 0.070 mmol) and 6-bromomethylquinoxaline (17.2 mg, 0.077 mmol) in CH3CN (anh., 10 mL) was added ethyldiisopropylamine (0.015 mL, 0.084 mmol). The mixture was heated in a 95 C. bath overnight. The reaction was cooled to room temperature and concentrated in vacuo. The residue was adsorbed onto silica gel. Silica gel chromatography using a gradient of 25% EtOAc/hexane to 50% EtOAc/hexane then 100% EtOAc afforded the title compound (23.2 mg) as an ivory powder. MS (ESI) m/z 478 [M+H]+; HPLC Method C, r.t.=10.9 min (98.9% a210-370 nm; 97.4% a 236 nm).

As the paragraph descriping shows that 53967-21-8 is playing an increasingly important role.

Reference£º
Patent; Wyeth; US2006/264631; (2006); A1;,
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98416-72-9, 6-Bromo-2-chloro-3-methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,98416-72-9

4.14 4-(-6-Bromo-3-methylquinoxalin-2-yloxy)benzaldehyde (14) p-Hydroxybenzaldehyde (0.01 mol) was dissolved in a mixture of acetonitrile (50 mL) and DMF (5 mL) containing anhydrous potassium carbonate (2.0 g). The mixture was refluxed for 1 h, then compound (5, 0.01 mol) was added and the mixture was further refluxed for 19 h (monitored by TLC). After completion of the reaction, the mixture was filtered and the excess of acetonitrile was evaporated under reduced pressure, dried and crystallized from mixture of benzene and petroleum ether to yield the crude product. Yield: 76%; (orange-brown powder): mp 101-103 C; IR (KBr) numax in cm-1: 2921 (aliphatic C-H), 2837, 2720 (CH-aldehyde), 1697 (C=O), 1597 (C=N); 1H NMR (DMSO-d6, 500 MHz): delta 2.74 (s, 3H, CH3), 7.58-8.04 (m, 7H, Ar-H), 10.04 (s, 1H, CHO); 13C NMR (DMSO-d6, 125 MHz): delta 20.49 (CH3), 122.47-133.54 (12Ar-C), 148.90, 149.52 (2C=N), 190.87 (CHO); MS (m/z), 342 (M+; 100%), 343 (M++1; 27%), 344 (M++2; 96%). Anal. Calcd for C16H11BrN2O2 (343.17): C, 56.00; H, 3.23; N, 8.16. Found: C, 56.19; H, 3.45; N.

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

Reference£º
Article; Abbas, Hebat-Allah S.; Al-Marhabi, Aisha R.; Eissa, Sally I.; Ammar, Yousry A.; Bioorganic and Medicinal Chemistry; vol. 23; 20; (2015); p. 6560 – 6572;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1204-75-7,3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid,as a common compound, the synthetic route is as follows.

A solution of 3-hydroxyquinoxaline-2-carboxylic acid, 9(500 mg, 2.63 mmol), and amino nitrile 6 (406 mg, 2.63 mmol) in anhydrous DMF (36 mL) was cooled down to 0Cin an ice/NaCl bath. To the cold solution, EDC¡¤HCl (1.50 g,7.89 mmol) and HOBt (1.46 g, 10.8 mmol) were added portionwiseover 30 min. The reaction mixture was stirred atroom temperature overnight and concentrated under vacuum.The resulting residue was taken CH2Cl2 (50 mL), treatedwith 2N NaOH until pH 14, and extracted with CH2Cl2 (3 ¡Á50 mL). The aqueous layer was treated with 1N HCl until pH1, extracted with CH2Cl2 (3 ¡Á 50 mL), and washed with brine(2 ¡Á 50 mL). The combined organic extracts were dried overanhydrous Na2SO4, concentrated under reduced pressure andthe resulting solid residue was washed with pentane (3 ¡Á 20mL), to provide amido nitrile 10 (730 mg, 85% yield) as ayellow solid; mp 181-182C; IR (ATR) nu 3081 (O-H, N-Hst), 2241 (CN st), 1678 (C=O st); 1H NMR (400 MHz,CD3OD) delta 1.41-1.50 (m, 8H), 1.61-1.71 (m, 4H), 2.43 (t, J =7.2 Hz, 2H), 3.48 (t, J = 7.2 Hz, 2H), 7.38 (dd, J = 8.4 Hz,J? = 1.2 Hz, 1H), 7.43 (ddd, J = 8.4 Hz, J? = 7.2 Hz, J? = 1.2Hz, 1H), 7.67 (ddd, J = 8.4 Hz, J? = 7.2 Hz, J? = 1.2 Hz,1H), 7.98 (dd, J = 8.4 Hz, J? = 1.2 Hz, 1H); 13C NMR (100.6MHz, DMSO-d6) delta 16.1, 24.7, 26.3, 28.0, 28.1, 28.5, 28.9,38.7, 115.57, 115.60, 120.7, 123.8, 129.2, 131.2, 131.7,132.4, 153.9, 163.0; HRMS (ESI), calcd for (C18H22N4O2 +H+) 327.1816, found 327.1817., 1204-75-7

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

Reference£º
Article; Artigas, Albert; Sola, Irene; Taylor, Martin C.; Clos, M. Victoria; Perez, Belen; Kelly, John M.; Munoz-Torrero, Diego; Letters in Organic Chemistry; vol. 15; 5; (2018); p. 455 – 461;,
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