Heterocyclic Building Blocks-quinoxaline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25983-13-5,6,7-Dichloroquinoxaline-2,3(1H,4H)-dione,as a common compound, the synthetic route is as follows.

General procedure: 2,2?-Bipyridine (0.071 g, 0.455 mmol) was added to a solution containing 0.100 g (0.454 mmol) of Cr(CO)6 in 50 mL of THF. The mixture was refluxed for 2 h with continuous stirring. The resulting orange colored solution was cooled down to room temperature. DCQX (0.104 g, 0.450 mmol) was dissolved in 20 mL of EtOH and slowly added to the reaction mixture. The contents were refluxed for 18 h with continuous stirring, and during this time the brown solid product separated from solution. The solid was isolated, washed with 15 mL THF/EtOH (1:1) and dried in vacuum. A concentrated solution of the product in DMSO/EtOH (3:1) was allowed to evaporate slowly for 2 weeks, which resulted in a reddish-brown powder. Washing the powdery solid with EtOH followed by diethyl ether and then drying overnight in vacuum resulted in 0.13 g (59.6% yield) of the pure product (one brown spot in a TLC test). Attempts to obtain crystals suitable for X-ray crystallography were unsuccessful due to the limited solubility of the synthesized complex in most common solvents. Anal. Calc. for C40H34Cl4Cr2N8O6 (Mr = 968.55): C, 49.60; H, 3.54; Cl, 14.64; N, 11.57. Found: C, 49.53; H, 3.52; Cl, 14.70; N, 11.62%. Effective magnetic moment at 298 K, mueff (BM): 2.955., 25983-13-5

The synthetic route of 25983-13-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Attia, Attia S.; Abdel Aziz, Ayman A.; Alfallous, Khalifa A.; El-Shahat; Polyhedron; vol. 51; 1; (2013); p. 243 – 254;,
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6924-66-9, Quinoxaline-5-carboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

PyBOP (149 mg, 287 muiotaetaomicronIota) was added to a mixture of quinoxaline-5-carboxylic acid (45.4 mg, 261 muiotaetaomicronIota), 8-amino-2-(3-chlorophenyl)-2-azaspiro[4.5]decan-1 -one (isomer 1 , Intermediate I50) (80.0 mg, 287 muiotaetaomicronIota) and N,N-diisopropylethylamine (180 muIota, 1 .0 mmol) in DMF (2.6 ml) and the mixture was stirred over night at room temperature. For work-up, water (45 ml) and methanol (2 ml) were added and the mixture was stirred for 4 h. The precipitate was collected by filtration, washed with a mixture of water and methanol (4:1 ) and dried to give the title compound 109 mg (93 % yield).LC-MS (Method 1 ): Rt= 1 .22 min; MS (ESIpos): m/z = 435 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1 .494 (2.45), 1 .506 (2.64), 1 .524 (2.94), 1 .535 (2.88) 1 .555 (1 .60), 1 .566 (1.50), 1 .650 (1 .19), 1.660 (1 .47), 1.683 (10.64), 1.706 (3.13), 1 .714 (3.63) 2.012 (3.13), 2.023 (3.32), 2.046 (3.09), 2.055 (2.76), 2.081 (5.42), 2.099 (9.45), 2.116 (5.61 )2.327 (0.87), 2.518 (2.62) 2.523 (1.85), 2.669 (0.91 ), 2.729 (0.63), 2.888 (0.76), 3.804 (5.72) 3.813 (1 .63), 3.822 (9.67) 3.829 (1.66), 3.839 (5.52), 3.888 (1.32), 3.898 (1 .62), 3.907 (1 .29) 3.917 (1 .57), 3.927 (1 .22) 7.189 (3.31 ), 7.191 (3.67), 7.194 (3.70), 7.196 (3.56), 7.209 (3.89) 7.21 1 (4.22), 7.214 (4.32) 7.216 (4.10), 7.394 (5.26), 7.415 (9.49), 7.435 (5.33), 7.589 (3.61 ) 7.591 (3.98), 7.594 (3.89) 7.596 (3.88), 7.610 (3.00), 7.61 1 (3.01 ), 7.615 (3.35), 7.617 (2.95) 7.910 (5.41 ), 7.916 (10.28), 7.921 (5.48), 7.960 (5.22), 7.977 (5.64), 7.981 (6.35), 7.999 (5.99) 8.253 (6.1 1 ), 8.257 (6.58), 8.274 (5.36), 8.278 (5.38), 8.430 (6.23), 8.433 (6.27), 8.448 (5.77) 8.452 (5.22), 9.069 (7.93), 9.074 (16.00), 9.080 (15.91 ), 9.084 (7.60), 9.770 (4.17), 9.788 (4.13), 6924-66-9

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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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7251-61-8,2-Methylquinoxaline,as a common compound, the synthetic route is as follows.,7251-61-8

To a 80 mL microwave tube was added 2-methylquinoxaline (0.576 g, 4 mmol), Fe (NO3)3¡¤ 9H2O (0.808 g, 2 mmol) and DMSO (50 mL) were heated to 135 C for 3 min at 150 W in a CEM Discover microwave reactor.After completion of the reaction, the mixture was cooled to room temperature, filtered and the filtrate was poured into saturated NaHCO3Aqueous solution, ethyl acetate (3 x 30 mL), and the combined organic layers were washed with anhydrous Na2SO4After drying, it was concentrated under reduced pressure and recrystallized from n-hexane (35 mL) to give 0.506 g of a yellow target product in 80% yield.

As the paragraph descriping shows that 7251-61-8 is playing an increasingly important role.

Reference£º
Patent; ZHEJIANG UNIVERSITY OF TECHNOLOGY; XIE, YUANYUAN; XIE, TINGHUI; HUANG, YINGYI; GAN, BING; YAN, YIYAN; LI, PINGPING; (10 pag.)CN106083713; (2016); A;,
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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: To the flask containing a mixture of substituted benzaldehyde (1mmole) and 2-aminophenol (1mmole) was added silica chloride(1 eq) and was heated on a sand bath at 120 C, TLC was taken afterevery 1 h. After 4 h, TLC showed appearance of new spot. The productwas isolated by first separating out the catalyst by filtration using organicsolvent; the organic layer was dried using anhydrous sodiumsulfate and evaporated under vacuum. The solid thus obtained was recrystallized using petroleum ether and its % yield and melting pointswere determined. The results are tabulated in Table 1 and Table 2.

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

Reference£º
Article; Desai, Sulaksha; Desai, Vidya; Shingade, Sunil; Bioorganic Chemistry; vol. 94; (2020);,
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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.,49679-45-0

A solution of ethyl 3-chloroquinoxaline-2-carboxylate (500 mg, 2.12 mmol) in morpholine (5 mL was stirred for 1 hour at 100C. It was diluted with water, extracted with EA (x3), washed with brine (x2). The organic layer was dried and concentrated to give 450 mg (crude) of desired compound as yellow oil, which was used directly in the next step without further purification. ESI MS m/z = 287.5 [M+H]+.

As the paragraph descriping shows that 49679-45-0 is playing an increasingly important role.

Reference£º
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; LIN, Kai; RHODIN, Michael, H.J.; McALLISTER, Nicole, V.; OR, Yat, Sun; (447 pag.)WO2019/67864; (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.83570-42-7,1-(Quinoxalin-6-yl)ethanone,as a common compound, the synthetic route is as follows.

83570-42-7, To a stirred solution of 1-(quinoxalin-6-yl)ethan-1 -one (0.8 g,4.65mmol) in dry MeOH (20 mL), sodium borohydride (0.36 g, 9.3 mmol ) was added portion wise at 0 C and the resulting mixture was stirred for 1 h. It was then concentrated, diluted with DCM (80 mL), washed with water (20 mL), dried over Na2SO4 and concentrated. The crude product was taken for next step without further purification. Yield: 75% (600 mg, dark brown liquid). 1H NMR (400 MHz, DMSO-d6): delta 8.91 -8.89 (m, 2H), 8.03 (t, J = 11.6 Hz, 2H), 7.87-7.86 (m, 1 H), 5.49 (d, J = 5.9 Hz, 1 H), 4.97 (t, J = 6.2 Hz, 1 H), 1.42 (d, J = 8.6 Hz, 3H). LCMS: (Method A) 175.0 (M+H), Rt. 1.89 min, 95.0% (Max).

The synthetic route of 83570-42-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
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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

In a round bottomed flask, thionyl chloride (8.5 mL, 117 mmol) was added to methanol (60 mL) and the resulting solution was cooled to 0 C. Quinoxaline-2-carboxylic acid 1 (5 g, 28.7 mmol) was then added by small portions over 5 min. At the end of the addition, the mixture was returned to ambient temperature and stirred overnight. The progress of the reaction could be followed by TLC (dichloromethane/methanol: 25/1). At the end of the reaction, the solvent and excessthionyl chloride were evaporated under reduced pressure and the crude residue was neutralized with Na2CO3 (saturated solution, 30 mL). The product was extracted with dichloromethane (520 mL). The combined organic layers were washed with brine and dried over MgSO4. After filtration, the solvent was evaporated to dryness. The methyl ester 2 was obtained as a brown powder.

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

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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6298-37-9, Quinoxalin-6-amine is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0269] A 20 mL vial was charged with picolinic acid (244 mg, 1.981 mmol), quinoxalin-6- amine (250 mg, 1.722 mmol), HATU (851 mg, 2.239 mmol), DMF (6 mL) and Et3N (0.720 mL, 5.17 mmol). The reaction mixture was stirred at 70C for 3 hours, then water was added and a precipitate was formed. The precipitate was isolated by filtration, washed with water, and dried under vacuum overnight to give the title compound. NMR (400 MHz, CD.iCN) delta ppm 7.65 (ddd,.7=7.64, 4.74, 1.26 Hz, 1H), 8.05 (td, J=7.71, 1.77 Hz, 1H), 8,08 – 8.12 (m, 1H), 8.15 – 8.20 (m, 1H), 8.29 (dt,,7=7,83, 1.01Hz, 1H), 8,69 (d, J=2.27 Hz, 1H), 8.74 (d, J=4.84 Hz, 1

6298-37-9, As the paragraph descriping shows that 6298-37-9 is playing an increasingly important role.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (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.13708-12-8,5-Methylquinoxaline,as a common compound, the synthetic route is as follows.

Reference Example 74 2-[N-(3-Cyanophenyl)-N-(5-quinoxalinylmethyl)amino]-N-[4-(1-trifluoroacetylpiperidin-4-yl)phenyl]acetamide 5-Methylquinoxaline (710 mg) and 920 mg of N-bromosuccinimide were dissolved in 8 ml of carbon tetrachloride, 50 mg of 2,2′-azobis(isobutyronitrile) was added to the solution, and the mixture was heated under reflux under an argon atmosphere for 5 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in 8 ml of isopropanol. To the solution were added 0.60 ml of N-ethyldiisopropylamine, 418 mg of sodium iodide and 1.0 g of 2-(3-cyanophenylamino)-N-[4-(1-trifluoroacetylpiperidin-4-yl)phenyl]acetamide, and the mixture was heated under reflux for 45 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane) to give 560 mg of 2-[N-(3-cyanophenyl)-N-(5-quinoxalinylmethyl)amino]-N-[4-(1-trifluoroacetylpiperidin-4-yl)phenyl]acetamide. 1H-NMR(CDCl3) delta ppm: 1.56-1.72 (2H, m), 1.85-2.00 (2H, m), 2.70-2.93 (2H, m), 3.16-3.30 (1H, m), 4.05-4.17 (1H, m), 4.21 (2H, s), 4.60-4.72 (1H, m), 5.33 (2H, s), 7.00-7.19 (5H, m), 7.23-7.38 (3H, m), 7.53-7.61 (1H, m), 7.70-7.80 (1H, m), 8.05-8.26 (2H, m), 8.80-8.94 (2H, m)

13708-12-8, The synthetic route of 13708-12-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kissei Pharmaceutical Co., Ltd.; EP1020434; (2000); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34117-90-3,3-Chloroquinoxalin-2-amine,as a common compound, the synthetic route is as follows.

tBuLi (2.0 mL, 3.28 mmol, 1.64 M in pentane) was added dropwise to a solution of diphenylphosphane (0.56 mL, 3.22 mmol) in Et2O (10 mL) at 70C. After stirring for 15 min at 30C the yellow suspension was cooled again, and a solution of 2a (578 mg, 3.22 mmol) in Et2O (10 mL) was added slowly at 70C (rapid addition leads to a brown side product) and stirred for 1 h. Then the mixture was allowed to warm to room temperature and stirred overnight. 31P NMR monitoring displayed signals for 3a and Ph2PH in an intensity ratio of 17:83%. The mixture was cooled to 80C, and a second equivalent of cold tBuLi in pentane (2.0 mL) was added. The mixture was allowed to warm to room temperature (brown colour) und stirred for 2 d (31P NMR signal ratio of 3a and Ph2PH, 60:40%). The precipitate was filtered off and washed with ether. (The brown colour vanishes on contact with traces of moisture.) After the major part of the solvent was removed in vacuum the product started to crystallize. The mixture was overlayered with hexane and after some hours filtered, washed with hexane/Et2O and dried in vacuum to give 440 mg (42%) orange-yellow crystals. Mp: 158-160C. Single crystals were obtained from warm saturated hexane/Et2O solution. 1H NMR (CDCl3) d: 5.31 (br s, 2H, NH2), 7.29 (superimposed td, 3J = 8, 7, 4J?1.2 Hz, 1H, H-6), 7.25-7.35 (m, 7H, aryl), 7.39-7.46 (m, 4H, aryl), 7.48 (td, 3J = 8,7, 4J?1.2 Hz, 1H, H-7), 7.55 (dd, 3J = 8.3, 4J?1.2 Hz, 1H, H-8), 7.72 (dd, 3J = 8.3, 4J?1.2 Hz, 1H, H-5). 13C{1H} NMR (CDCl3) d: 124.70 (CH-6), 125.60 (CH-8), 128.57 (d, 3J = 7.4 Hz, 4 CH-m), 129.51 (2 CH-p), 129.46, 130.34 (CH-5, CH-7), 133.25 (d, 1J = 5.4 Hz, 2 Cq-i), 134.45 (d, 2J = 19.6 Hz, 4 CH-o), 138.78 (d, 3J = 3.3 Hz, Cq-4a), 141.05 (Cq-8a), 149.24 (d, 1J = 13.0 Hz, PCq-3), 153.60 (d, 2J = 24.3 Hz, NCq-2). 31P{1H} NMR (CDCl3) d: 12.1. UV-VIS (c = 3.4¡Á10-5 mol/L) lambdamax(MeOH)/nm (epsilon/dm3 mol-1 -cm-1): 371 (6730), 306 (3560), 244 (19500), 208 (38400). Anal. Calc. for C20H16N3P (329.33): C, 72.94; H, 4.90; N, 12.76. Found: C, 73.07; H, 4.89; N, 12.87%.

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

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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