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

After adding 6-bromoquinoxaline (3.8 g, 18.2 mmol), n-butyl vinyl ether (12.3 mL, 95.2 mmol), potassium carbonate (3.1 g, 22.8 mmol), 1,3-bis(diphenylphosphino)propane (504 mg, 1.3 mmol) and palladium(II) acetate (124 mg, 0.5 mmol) to N,N-dimethylformamide (47 mL) and water (6 mL), the result was stirred and refluxed for 6 hours. After terminating the reaction, the result was cooled to room temperature, 2 N hydrochloric acid was added thereto, and the result was stirred for 0.5 hours. Ethyl acetate was added thereto, the organic layer was washed with water and sodium bicarbonate, dried using anhydrous magnesium sulfate, and filtered. The filtrate was concentrated and purified using column chromatography to obtain a target compound (2.4 g). 1H NMR spectrum (300 MHz, DMSO-d6) delta 10.05(d, 1H), 9.73(t, 1H), 8.71(s, 1H), 7.97(d, 1H), 3.16(s, 3H).

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

Reference£º
Patent; Hanmi Pharmaceutical Co., Ltd.; LEE, Kyung Ik; JUNG, Young Hee; SONG, Ji Young; JUN, Seung Ah; (89 pag.)EP3480193; (2019); 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

A solution of 2-chloro-3-methylquinoxaline L [45] (500mg, 2.8mmol) and 3-trifluoromethylaniline (2,5mL, 20mmol) in anhydrous DMF (10mL) was heated at 140C in a sealed vial under microwave irradiation. After completion of the reaction (45min), CH2Cl2 was added, and the organic phase was washed successively with 1M HCl and brine. The organic layer was then dried with Na2SO4, filtered and evaporated. The resulting solid was purified by silica gel column chromatography (eluent: CH2Cl2) to afford 3-Methyl-N-(3-(trifluoromethyl)phenyl)quinoxalin-2-amine. Yield 69%. Amber powder. mp 98C. 1H NMR (250MHz, CDCl3) delta=8.24 (s, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.87 (dd, J=8.1, 1.1 Hz, 1H), 7.78 (dd, J=8.2, 1.0 Hz, 1H), 7.64-7.53 (m, 1H), 7.52-7.39 (m, 2H), 7.37-7.27 (m, 1H), 6.77 (bs, 1H, NH), 2.65 (s, 3H). 13C NMR (63MHz, CDCl3) delta=147.7, 144.6, 140.3 (d, J=3.2 Hz), 137.9, 131.5 (q, J=33.1 Hz), 129.4 (d, J=6.0 Hz), 128.2, 126.9, 126.1, 124.3 (q, J=272.9 Hz), 122.8, 119.6 (d, J=3.8 Hz), 116.6 (d, J=3.4 Hz), 21.03. LC-MS (ESI, 35 eV): tR=4.75min, m/z 304 [M+H]+., 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; 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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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.

General procedure: The tail group containing monomer, dimer ortrimer (0.266 mmol) was dissolved in methanol (25 mL), to which Pd/C-10% (60mg) was added at 0oC under nitrogen with stirring. The reactionmixture was hydrogenated at room temperature and atmospheric pressure for 4 h.The catalyst was removed over Kieselguhr and the solvent was removed underreduced pressure to give the amine, which was dissolved in DMF (1 mL, dry). Theappropriate head group carboxylic acid (0.266 mmol) was dissolved in DMF (1 mL,dry) to which HBTU (260 mg, 0.685 mmol) and triethylamine (50 muL) were added tothe reaction mixture at room temperature with stirring and the reaction mixturewas left standing at room temperature overnight. The product was purified byHPLC (no work up required). Fractions containing the product were collected andfreeze dried to give the required product., 879-65-2

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

Reference£º
Article; Scott, Fraser J.; Puig-Sellart, Mireia; Khalaf, Abedawn I.; Henderson, Catherine J.; Westrop, Gareth; Watson, David G.; Carter, Katharine; Grant, M. Helen; Suckling, Colin J.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3478 – 3486;,
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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.

(1) To a solution of ethyl 3-chloroquinoxaline-2-carboxylate (2.00 g, 8.41 mmol) was added sodium methoxide (28% in methanol, 3.60 g, 18.7 mmol) at 0 C. After being stirred for 1 hour at room temperature, the reaction mixture was diluted with dichloromethane (200 mL). The solution was neutralized with ammonium chloride and filtrated through celite. The filtrate was combined and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:2), followed by trituration with hexane to give ethyl 3-methoxyquinoxaline-2-carboxylate as colorless powder (1.37 g, 74%). MS (APCI): m/z 219 (M+H).

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

Reference£º
Patent; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); A1;,
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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.

0180] First, 3.02 g of 2-chloro-3-methylquinoxaline, 3.88 g of 3,5-dimethylphenyl boronic acid, 2.77 g of sodium carbonate, 0.14 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of DMF were put in a recovery flask equipped with a reflux pipe, and the air in the flask was replaced with argon. Heating was performed by irradiation with microwaves (2.45 GHz, 100 W) for 2 hours. Then, water was added to this solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and saturated saline, and was dried with magnesium sulfate. The solution obtained by the drying was filtered. The solvent of this solution was distilled off, and the obtained residue was purified by flash column chromatography using hexane and ethyl acetate in a volume ratio of 5: 1 as a developing solvent. The solid obtained by concentration of a fraction was purified by flash column chromatography using dichloromethane as a developing solvent to give a target quinoxaline derivative, Hmdmpq, as flesh color powder in a yield of 72 %. Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). Synthesis Scheme (b- 1) of Step 1 is shown below. [0181]

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; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; INOUE, Hideko; YAMAGUCHI, Tomoya; SEO, Hiromi; TAKAHASHI, Tatsuyoshi; SEO, Satoshi; WO2014/199842; (2014); 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.

To a solution of 11i (30 mg, 110 mumol), 6-bromoquinoxaline (41.8 mg, 200 mumol), Bu4NOAc (78.3 mg, 260 mumol) and Pd(OAc)2 (4.4 mg, 19.6 mol) in NMP (0.5 mL ). The reaction mixture was stirred for 13 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 12i (8.4 mg, 19%) as a yellow solid. TLC: Rf 0.29 (1:1 hexane/EtOAc). mp: 164166 oC. 1H-NMR (400 MHz, CDCl3) delta 8.93 (d, 1H, J = 2.0 Hz), 8.88 (d, 1H, J = 2.0 Hz), 8.18 (d, 1H, J = 8.8 Hz), 8.08 (d, 1H, J = 2.0 Hz), 7.77 (dd, 1H, J = 8.8 Hz, J = 2.0 Hz), 7.74 (t, 1H, J = 8.0 Hz), 7.65 (d, 1H, J = 8.0 Hz), 7.15-7.10 (m, 3H), 6.73 (tt, 1H, JHF = 8.8 Hz, JHH = 2.4 Hz), 2.17 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 163.3 (dd, JCF = 246.9 Hz, JCF = 13.1 Hz), 158.4, 148.9, 146.3, 146.0, 144.0, 143.2, 142.8, 139.3, 133.6, 133.2, 132.3, 131.7, 130.3, 130.0, 124.0, 115.6, 110.5 (dd, JCF = 19.3 Hz, JCF = 7.6 Hz), 103.9 (t, JCF = 24.9 Hz), 23.8. HRMS (ESI) calcd. for C22H15F2N6 (M+H): 401.1321; found 401.1327., 50998-17-9

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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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

Example 5. 3,7-bis[(quinoxalin-6-yl)carbonyl]-1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one (compound 5 corresponding to general formula 1.3).; To a solution of 34.8 g (0.2 mole) of quinoxaline-6-carboxylic acid in absolute dimethylformamide, 35.64 g (0.22 mole) of CDI were added while stirring and cooling in an ice bath. Stirring was carried out for five hours. Then a solution of 24.1 g (0.1 mole) of 1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one hydrochloride in DBU (1,8-diazabicyclo[5.4.0]undene-7) was added to the reaction mixture. The reaction was heated up to 50C and heated for eight hours. Then precipitate was filtered off. Filtrate was evaporated to dryness. The residue was applied on a chromatographic silica gel column. Chlorophorm was used as an eluent. A fraction with Rf=0.52 was recovered on silufol in the CHCl3-EtOH (20:1) system. Solvent was distilled off, and a clear oil was obtained which over time was crystallized. Yield: 64%. 1HNMR (CDCl3 delta, ppm): 0.97 s(6H); 3.00 d (2H, J 12 Hz); 3.34 d(2H, J 12 Hz); 4.22 d (2H, J 12 Hz); 4.84 d (2H, J 12 Hz); aromatic protons [7.80 d (1H, J=5.8 Hz), 8.18 s (1H), 8.20 d (1H, J=5.8 Hz)].

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

Reference£º
Patent; Institute of Physiologically active compunds of the Russian Academy of Sciences (IPAC RAN); EP2088149; (2009); 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

General procedure: Aminophenol (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 (5, 0.01 mol)was added and the mixture was further refluxed for 6 h (monitoredby TLC). After completion of the reaction, the mixture was filteredand the excess of acetonitrile was evaporated under reduced pressureand crystallized from ethanol to give the correspondingcompounds. 4.12.1 2-[6(7)-Bromo-2-methylquinoxalin-3-yloxy]aniline (12a) The compound 12a was obtained from the reaction of o-aminophenol. Yield: 64%; (orange powder): mp 119-121 C; IR (KBr) numax in cm-1: 3412, 3325 (NH2), 2921, 2825 (aliphatic C-H), 1603 (C=N); 1H NMR (DMSO-d6, 500 MHz): delta 2.75 (s, 3H, CH3), 4.45 (br s, 2H, NH2; exchangeable with D2O), 6.83-7.73 (m, 7H, Ar-H); 13C NMR (DMSO-d6, 125 MHz): delta 20.68 (CH3), 122.60-138.01 (12Ar-C), 143.94, 149.65 (2C=N); MS (m/z), 314 (M+-CH3; 100%), 329 (M+; 35%), 330 (M++1; 13%), 331 (M++2; 34%). Anal. Calcd for C15H12BrN3O (230.18): C, 54.56; H, 3.66; N, 12.73. Found: C, 54.78; H, 3.91; N, 12.63.

As the paragraph descriping shows that 98416-72-9 is playing an increasingly important role.

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.41959-35-7,6-Nitro-1,2,3,4-tetrahydroquinoxaline,as a common compound, the synthetic route is as follows.

To a stirred solution of 789 6-nitro-1,2,3,4-tetrahydroquinoxaline (0.5 g, 2.79 mmol, 1.0 eq) in 743 DCM (20 mL) was added 155 triethylamine (1.17 mL, 8.37 mmol, 3.0 eq) and 790 DMAP (68 mg, 0.558 mmol, 0.2 eq) at rt. The resulting mixture was allowed to cool to 0 C. followed by addition of 482 di-tert-butyl dicarbonate (1.41 mL, 6.139 mmol, 2.2 eq), the reaction mixture was stirred at RT for overnight. The progress of reaction was monitored by LCMS. The reaction mixture was diluted with DCM (50 mL), and washed with water (2¡Á50 mL) dried over Na2SO4, filtered and concentrated and purified by combi flash [silica gel 100-200 mesh; elution 0-35% 19 EtOAc in 20 Hexane] to afford the desired compound 791 di-tert-butyl 6-nitro-2,3-dihydroquinoxaline-1,4-dicarboxylate (0.65 g, 61.43%) as yellow viscous. (0776) LCMS: (M+1)+380.4., 41959-35-7

41959-35-7 6-Nitro-1,2,3,4-tetrahydroquinoxaline 10197942, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; KUMAR, Varun; (360 pag.)US2019/106436; (2019); A1;,
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55687-02-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.

Methyl (S)-1-((S)-2-(5-(4-(6-bromoquinoxalin-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate A mixture of methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (5 g, 10.1 mmol), 6-bromo-2-chloroquinoxaline (2.94 g, 12.1 mmol), cesium carbonate (6.51 g, 20.1 mmol), dioxane (100 mL) and water (10 mL) was degassed and flashed with nitrogen three times. Tetrakis(triphenylphosphine)palladium (0) (1.16 g, 1.01 mmol) was then added to the mixture. The mixture was then heated at 80 C. overnight while stirring. Solvent was then removed by evaporation in vacuo. The solid residue was treated with DCM and water to make a biphasic solution. The dichloromethane layer was separated, dried over sodium sulfate, filtered and evaporated. The black crude product was purified by column (0-5% MeOH in DCM) to give a deep colored solid product, methyl (S)-1-((S)-2-(5-(4-(6-bromoquinoxalin-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (5.47 g, 94%): ESI-LRMS m/e calcd for C28H29BrN6O3 [M+] 578, found 579 [M+H+].

The synthetic route of 55687-02-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Alam, Muzaffar; Berthel, Steven Joseph; Brinkman, John A.; Hawley, Ronald Charles; Li, Hongju; Palmer, Wylie Solang; Pietranico-Cole, Sherrie; Sarabu, Ramakanth; Smith, Mark; So, Sung-Sau; Yi, Lin; Zhai, Yansheng; Zhang, Qiang; Zhao, Shu-Hai; US2012/230951; (2012); A1;,
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