Heterocyclic Building Blocks-quinoxaline

6298-37-9,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.

A mixture of tert-butyl (4-nitrophenyl) butane-1,4-diyldicarbamate (3) (550 mg,1.55 mmol), quinoxalin-6-amine (339 mg,2.33 mmol), DMF (6.6 mL), and Et3N (0.43 mL, 3.11 mmol) in a 20 mL microwave vial washeated in a Biotage microwave at normal absorption for 2.75 h at 80 C. Solvent was removed invacuo. The crude product was purified on a silica cartridge (40 g) with a CombiflashCompanion, eluting at 35 mL/min with a gradient running from 100% DCM to 100 % EtOAcover 55 min to afford the free base tert-butyl (4-(3-(quinoxalin-6-yl)ureido)butyl)carbamate (334mg, 0.890 mmol, 60 % yield) LCMS (ES)+ [M+H]+ = 360.2 (0.78 min).

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

Reference£º
Article; Boehm, Jeffrey; Davis, Roderick; Murar, Claudia E.; Li, Tindy; McCleland, Brent; Dong, Shuping; Yan, Hongxing; Kerns, Jeffrey; Moody, Christopher J.; Wilson, Anthony J.; Graves, Alan P.; Mentzer, Mary; Qi, Hongwei; Yonchuk, John; Kou, Jen-Pyng; Foley, Joseph; Sanchez, Yolanda; Podolin, Patricia L.; Bolognese, Brian; Booth-Genthe, Catherine; Galop, Marc; Wolfe, Lawrence; Carr, Robin; Callahan, James F.; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 579 – 588;,
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17056-99-4, Quinoxalin-5-ol is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. Diethylthiocarbamic acid O-quinoxalin-5-yl ester. ; A mixture of 5-hydroxyquinoxaline (2.13 g, 14.6 mmol), finely ground K2CO3 (4.0 g, 29 mmol), and DMF (50 mL) was stirred at 23 C. for 1 h. Solid diethylthiocarbamoyl chloride (2.439 g, 16.1 mmol) was then added. The resulting mixture was stirred for 2 h, then was diluted with water (150 mL) and extracted with Et2O (2¡Á100 mL). The combined organic extracts were washed with water (100 mL) and brine (100 mL), then dried and concentrated to a viscous orange oil, which was used without purification (3.63 g, 95%). MS (ESI+): mass calcd. for C13H15N3OS, 261.1; m/z found, 262 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.85-8.65 (m, 2H), 7.96 (dd, J=8.5, 1.1, 1H), 7.71 (t, J=7.9, 1H), 7.46 (dd, J=7.6, 1.2, 1H), 3.87 (q, J=7.1, 2H), 3.78 (q, J=7.1, 2H), 1.38 (t, J=7.1, 3H), 1.28 (t, J=7.1, 3H). 13C NMR (125 MHz, CDCl3): 186.6, 149.4, 144.9, 144.5, 143.4, 137.0, 128.9, 127.0, 123.1, 48.2, 44.5, 13.1, 11.5.

17056-99-4, The synthetic route of 17056-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Allison, Brett; Phuong, Victor K.; Pippel, Marna C.W.; Rabinowitz, Michael H.; Venkatesan, Hariharan; US2006/69286; (2006); 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

50998-17-9, 6-Bromo quinoxaline (2.0 g, 9.5 mmcl) in toluene (20 mL) was degassed for 30 mm. To thissolution, 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 HCI solution in water (20 mL) was added and the mixture was stirred for I hour at rt. It was concentrated and neutralized with sat. NaHCO3. The desired product wasextracted with DCM (100 mL), dried over Na2SO4 and concentrated. The crude productwas purified by column chromatography to afford the title compound (brown solid). 1H NMR(400 MHz, DMSO-d6): 6 9.06-9.04 (m, 2H), 8.70 (d, J=2.4 Hz, I H), 8.28 (t, J = 2.8 Hz, I H),8.16 (d, J = 11.6 Hz, IH), 2.97 (5, 3H). LCMS: (Method A) 173 (M+H), Rt. 2.25 mm,99.06% (Max).

The synthetic route of 50998-17-9 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; (280 pag.)WO2017/144633; (2017); A1;,
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108229-82-9, 6-Bromo-2,3-dichloroquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 16 9-Bromo-1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxaline and 10-bromo-1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxaline The above compounds are obtained when 6-bromo-2,3-dichloro quinoxaline is treated with 2-piperidinomethanol by the procedure of Example 2.

108229-82-9, The synthetic route of 108229-82-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; American Cyanamid Company; US4200748; (1980); A;,
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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 suspension of NaH (33.7 mg, 842 muetaiotaomicron) in DMF (3 ml) at 0 under an argon atmosphere was added (6-(pyrrolidin-l-yl)pyridin-2-yl)methanol (0.1 g, 561 muiotaetaomicron) and 2-chloro-3- methylquinoxaline (150 mg, 842 muiotaetaomicron). The mixture was stirred at 0 for 2.5 firs. At 0 water was given to the reaction mixture. The product was extracted with EtOAc, washed with water, dried over MgSC^, filtered and evaporated. The crude product was purified by column chromatography using a CH2Cl2/MeOH gradient as eluent, providing the title compound (0.15 g, 83%) as off-white solid. MS: M = 321.1 (M+H)+

32601-86-8, 32601-86-8 2-Chloro-3-methylquinoxaline 236276, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; LERNER, Christian; WO2013/178569; (2013); A1;,
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7251-61-8, 2-Methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A 25 mL pressure vial was charged with 2-methylquinoline (1a) (71.5 mg, 0.50 mmol, 1.0 equiv.), I2 (317.3 mg, 1.25 mmol, 2.5 equiv.) and DMSO (3.0 mL). The vial was sealed and the resulting mixture was stirred at 110 C for 4-6 h under an air atmosphere, after disappearance of the reactant (monitored by TLC), then added benzohydrazide (2a) (81.6 mg, 0.6 mmol, 1.2 equiv.) , K2CO3 (414.0 mg, 3.0 mmol, 6.0 equiv.) at 110 C for another 4-6 h. After the reaction completed, and added 50 mL water to the mixture, then extracted with EtOAc 3 times (3 ¡Á 50 mL). The extract was washed with 10% Na2S2O3 solution (w/w), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was puried by flash column chromatography on silica gel to yield the corresponding product 3aa as a yellow solid (72% yield)., 7251-61-8

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

Reference£º
Article; Shang, Zhi-Hao; Sun, Ji-Na; Guo, Jiang-Shan; Sun, Yuan-Yuan; Weng, Wei-Zhao; Zhang, Zhen-Xiao; Li, Zeng-Jing; Zhu, Yan-Ping; Tetrahedron; vol. 76; 6; (2020);,
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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.

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, EXAMPLE 8 Preparation of 5-chloro-7-[2-(pyridin-2-yl)ethyl]-2-(quinoxalin-2-yl)-benzoxazole This is prepared from 2-amino-4-chloro-6-[2-(pyridin-2-yl)ethyl]phenol and 2-quinoxaline carboxylic acid using method B to give the intermediate amide (32%). This is cyclised with methanesulphonic acid in toluene with azeotropic removal of water with a Dean-Stark trap to give the title compound as a white crystalline solid (9%), m.p 182-183 C. TLC (SiO2, EtOAc:hexanes 1:1, Rf=0.27). Mass spectrum CI (methane) m/z=387 [M+H]+.

879-65-2 2-Quinoxalinecarboxylic acid 96695, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Euro-Celtique, S.A.; US6166041; (2000); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2213-63-0,2,3-Dichloroquinoxaline,as a common compound, the synthetic route is as follows.

2-Amino-3-chloroquinoxaline (2a). The compound was synthesized by a slightly modified version of the procedure of Saikachi and Tagami [1] using a reaction temperature of only 80 C. Compound 1 (8.0 g, 40.2 mmol) was dissolved in N-methyl-2-pyrrolidinone (NMP) (60 mL) and heated to 80 ?C. Then, ammonia gas was bubbled through the hot solution for 3 h while the reaction was monitored by TLC. The crude product was poured into water (100 mL). The precipitate was collected by filtration, dried over CaCl2 and crystallized from chloroform to give 4.8 g (63%) pale yellow crystals, mp. 137-139 C. The NMR data are in accordance with a semihydrate. 1H-NMR (CDCl3): delta 1.85 (br, 1 H, 0.5 H2O), 5.53 (br s, 2 H, NH2), 7.47 (td, 3J = 8.3, 6.8, 4J = 1.7 Hz, 1 H, H-6), 7.63 (td, 3J = 8.3, 6.8, 4J = 1.4 Hz, 1 H, H-7), 7.69 (ddd, 3J = 8.3, 4J = 1.5, 5J = 0.5 Hz, 1 H, H-8), 7.86 ppm (ddd, 3J = 8.2, 4J = 1.3, 5J = 0.5 Hz, 1 H, H-5). 13C-NMR (CDCl3): delta 125.4 (CH-6), 126.1 (CH-8), 128.1 (CH-5), 130.6 (CH-7), 137.1, 137.3 (Cq-4a, Cq-3), 140.3 (Cq-8a), 148.7 ppm (Cq-2). MS (EI 70 eV, 165 ?C): m/z (%) = 181 (30) [M+(37Cl)], 179 (100) [M+(35Cl)], 144 (84), 117 (23), 102 (8), 90 (26), 44 (81). Water was separated by azeotropic distillation with toluene at normal pressure. Residual toluene was removed in vacuum. Anal. Calcd for C8H6ClN3 (179.61 gmol-1): C, 53.50; H, 3.37; N 23.40. Found: C, 53.59; H, 3.40; N 22.96.

2213-63-0, The synthetic route of 2213-63-0 has been constantly updated, and we look forward to future research findings.

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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55687-34-8, 6-Bromoquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 29 Isopropyl 7-(3-chlorophenyl)-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate To a solution of 7-bromo-3-oxo-3,4-dihydroquinoxaline (6.8 g, 30 mmol) in pyridine (50 ml) was added a solution of isopropyl chloroformate in toluene (35 ml, 1M, 35 mmol) over 30 minutes. The mixture was triturated with water/chloroform, the organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated to obtain crude isopropyl 7-bromo-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate(9.3 g, 97%). A sample was recrystallized from ethanol: mp. 159-161 C. 1H-NMR (DMSO-d6) delta1.25 (d, J=6.2 Hz, 6H), 4.25 (s, 2H), 4.90 (sep, J=6.2 Hz, 1H), 6.89 (d, J=8.6 Hz, 1H), 7.27 (dd, J=9.1, 2.1 Hz, 1H), 7.74 (s, 1H), 12.51 (s, 1H), MS (ESI) m/z 330/332 (M+NH4)+. The title compound was prepared according to the procedure for Example 5 from isopropyl 7-bromo-3-oxo-3,4-dihydroquinoxaline-1 (2H)-carboxylate (6.3 g, 20 mmol), and 3-chlorophenyl boronic acid (3.2 g, 20 mmol). Off-white crystals (3.7 g, 49%): mp. 174-176 C. 1H-NMR (DMSO-d6) delta1.27 (d, J=6.4 Hz, 6H), 4.30 (s, 2H), 4.94 (sep, J=6.2 Hz, 1H), 7.04 (d, J=8.3 Hz, 1H), 7.50 (m, 4H), 7.61 (t, J=1.9 Hz, 1H), 7.86 (s, 1H), 10.79 (s, 1H), MS(APCI) m/z 345/347 (M+H)+., 55687-34-8

As the paragraph descriping shows that 55687-34-8 is playing an increasingly important role.

Reference£º
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6380235; (2002); B1;,
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