Heterocyclic Building Blocks-quinoxaline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1865-11-8,Methyl quinoxaline-2-carboxylate,as a common compound, the synthetic route is as follows.

Methanolic ammonia (10 ml, 7N) was added to a compound methyl quinoxaiine-2-carhoxylate (1.1 g, 5.85 rnmol) at 0 ¡ãC and the reaction mixture was allowed to stir at room temperature for overnight. The reaction mixture was concentrated under reduced pressure and the crude material was purified by column chromatography on silica gel using Ethyl acetate/ilexane as an eluent to give the desired product quinoxaline-2-carboxamide (0.98 g, 566 mmoi, 97 percent ) as a solid.

1865-11-8, The synthetic route of 1865-11-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PI INDUSTRIES LTD.; SAXENA, Rohit; PANMAND, Deepak Shankar; JENA, Lalit Kumar; SRIVASTAVA, Khushboo; RAJU, Jella Rama; MANJUNATHA, Sulur G; SAMANTA, Jatin; GARG, Ruchi; AUTKAR, Santosh Shridhar; VENKATESHA, Hagalavadi M; GADAKH, Ramdas Balu; KLAUSENER, Alexander G. M.; POSCHARNY, Konstantin; (219 pag.)WO2018/116072; (2018); A1;,
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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

55687-34-8, EXAMPLE 2 6-Bromo-1-ethoxycarbonylmethylquinoxaline-2,3(1H,4H)-dione Under a nitrogen atmosphere 6-bromoquinoxalin-2(1H)-one (2.03 g, 9 mmol) (J.Med.Chem., 24, (1981), 93) was dissolved in 22 ml of dry DMF and sodium hydride (0.44 g, 10.8 mmol (60% mineral oil dispersion)) was added. After stirring for 2 h, ethyl bromoacetate (1.25 ml, 11.3 mmol) was added and the mixture was stirred for 3.5 h. The reaction mixture was poured onto crushed ice and acidified (pH=4.5) by addition of dilute hydrochloric acid. The precipitate was filtered off, washed with water and air dried. The crude product (containing a minor fraction of O-alkylated product) was triturated with ether (100 ml), the precipitate filtered off, washed with ether and dried to afford 1.95 g (80%) of pure 6-bromo-1-ethoxycarbonylmethylquinoxalin-2(1H)-one. 1 H-NMR (DMSO-d6):delta1.22 (t, 3H), 4.17 (q, 2H), 5.08 (s, 2H), 7.56 (d, 1H), 7.83 (dd, 1H), 8.09 (dd, 1H), 8.37 (s, 1H).

55687-34-8 6-Bromoquinoxalin-2(1H)-one 12686394, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Novo Nordisk A/S; US5166155; (1992); A;,
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82031-32-1, 7-Bromoquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

82031-32-1, 6.00 mg (2.67 mmol) of 7-bromoquinoxalin-2(lH)-one [Lumma et al., J. Med. Chem. 1981, 24, 93] and 1.73 ml (3.47 mmol) trimethylsilyldiazomethane were taken up in 5.25 ml methanol/acetonitrile/dichloromethane (1/10/10). Then 0.483 ml (3.47 mmol) triethylamine was added and it was stirred overnight at room temperature. The mixture was concentrated by evaporation and the residue was purified by MPLC (Puriflash Analogix: 4OM: isohexane / ethyl acetate = 9 / 1 ? isohexane / ethyl acetate = 3 / 1). We obtained 140 mg (22% of theor.) of the target compound.LC-MS (method 10): R, = 1.09 min; MS (EIpos): m/z = 240 [M+H]+.IH-NMR (400 MHz, DMSO-D6): delta [ppm] = 4.04 (s, 3H), 7.78 (dd, IH), 7.96 (d, IH), 8.06 (d, IH), 8.64 (s, IH).

82031-32-1 7-Bromoquinoxalin-2(1H)-one 4913264, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; KAST, Raimund; GRIEBENOW, Nils; MEIER, Heinrich; KOLKHOF, Peter; ALBRECHT-KUePPER, Barbara; NITSCHE, Adam; STASCH, Johannes-Peter; SCHNEIDER, Dirk; TEUSCH, Nicole; RUDOLPH, Joachim; WHELAN, James; BULLOCK, William; PLEASIC-WILLIAMS, Susan; WO2010/20363; (2010); A1;,
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36856-91-4, 2-Bromoquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A 25-mL round bottom flask equipped with a magnetic stirrer, a condenser and a nitrogen inloutlet adapter was charged with 2-bromoquinoxaline (100 mg, 0.48 mmol),4-Fluorophenylboronic acid (80 mg, 0.57 mmol), water dioxane (1.0 mL4.0 ml), K2C03 (132 mg, 0.96 mmol). The resulting solution was degassed for 15 mm, then Pd(PPh3)4 (27 mg, 0.024 mmol) was added. The reaction mixture was warmed to 100 C. and stirred for 1 h. Afier cooled to roomtemperature, the reaction mixture was diluted with EtOAc and washed with saturated NaHCO3, brine, dried over Na2504. The organic layer was concentrated under reduced pressure and purified on silica gel. Elution with EtOAc hexanes solvent system afforded the desired compound (40mg, 38% yield). 1H NMR (400 MHz, CDCl3) oe 9.34 (s, 1H),8.18 (m, 2H), 8.00 (m, 2H), 7.82 (m, 2H), 7.57 (m, 1H), 7.25 (m, 1H)., 36856-91-4

As the paragraph descriping shows that 36856-91-4 is playing an increasingly important role.

Reference£º
Patent; Rutgers, The State University of New Jersey; LaVoie, Edmond J.; Parhi, Ajit; Pilch, Daniel S.; Kaul, Malvika; (36 pag.)US9822108; (2017); B2;,
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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

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (149 mg, 0.778 mmol) was added to a methylene chloride solution (5.2 ml) of (2S)-1-{4-[(5-chloropyrimidin-2-yl)oxy]piperidin-1-yl}-3-methyl-1-oxobutan-2-amine dihydrochloride (200 mg, 0.519 mmol), 3-hydroxyquinoxaline-2-carboxylic acid (102 mg, 0.519 mmol), 1-hydroxybenzotriazole monohydrate (84.1 mg, 0.622 mmol) and N-methylmorpholine (0.285 ml, 2.59 mmol), at room temperature, and stirring was carried out at room temperature overnight. Water was added to the reaction solution, followed by extraction with methylene chloride, and the extract was washed sequentially with a saturated aqueous sodium hydrogencarbonate solution, water and saline, and dried over anhydrous sodium sulfate. After the organic layer was concentrated and the resulting residue was purified by silica gel column chromatography, the resulting residue was suspended in a mixed solvent of ethanol-diethyl ether, and then the solid substance was collected by filtration to afford the desired title compound (198 mg, yield 79%) as a yellow solid. 1H-NMR (CDCl3, 400 MHz) delta: 12.52 (1H, brs), 10.17 (1H, brs), 8.47-8.46 (2H, m), 8.05-8.00 (1H, m), 7.63-7.26 (3H, m), 5.30-5.06 (2H, m), 4.08-3.63 (4H, m), 2.35-1.91 (5H, m), 1.14-1.09 (6H, m). IR (KBr) cm-1: 2965, 1690, 1630, 1425. MS (ESI, m/z): 485 (M+H)+. HRMS (ESI, m/z): 507.1532 (Calcd for C23H25ClN6NaO4: 507.1524). Anal. Calcd for C23H25ClN6O4¡¤0.1H2O: C, 56.76; H, 5.22; N, 17.27; F, 7.28. Found: C, 56.56; H, 5.07; N, 17.20; F, 7.65.

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

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP2258697; (2010); A1;,
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55687-02-0,55687-02-0, 6-Bromo-2-chloroquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Pd(Ph3P)4 (28.5 mg, 0.025 mmol) was added to a degassed solution of 6- bromo-2-chloroquinoxaline (60 mg, 0.246 mmol), (lR,3S,5R)-tert-butyl 3-(6-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-benzo[d]imidazol-2-yl)-2- azabicyclo[3.1.0]hexane-2-carboxylate (1 15 mg, 0.271 mmol) and sodium bicarbonate (62.1 mg, 0.739 mmol) in dioxane (1 mL) and FLO (0.2 mL) and the mixture was stirred at 1 10 C for 2 h and then at 120 C for 2 h. The reaction was diluted with MeOH, filtered and purified by prep HPLC (H20-MeOH with lOmM NH4OAc buffer) to yield (lR,3S,5R)-tert-butyl 3-(6-(6-bromoquinoxalin-2-yl)-lH-benzo[d]imidazol-2-yl)-2- azabicyclo[3.1.0]hexane-2-carboxylate (102.2 mg, 0.202 mmol, 82 % yield) as bright yellow solid. LC-MS retention time 2.31 min; m/z 506 [M+H] . (ColumnPHENOMENEX Luna 3.0 x 50mm S 10. Solvent A = 90% water: 10% methanol: 0.1% TFA. Solvent B = 10% water:90% methanol: 0.1% TFA. Flow Rate = 4 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 3 min. Wavelength = 220).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; PACK, Shawn, K.; TYMONKO, Steven; PATEL, Bharat, P.; NATALIE, JR., Kenneth, J.; BELEMA, Makonen; WO2011/59850; (2011); A1;,
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7712-28-9, 3-(3-Hydroxyquinoxalin-2-yl)propanoic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7712-28-9, In a typical reaction, AMA 2:3 (10mmol), the corresponding carboxylic acid (1mmol) and the alcohol (2ml) were mixed in the provided reaction glass tube equipped with a screw cap and magnetic agitation until a wet mixture was achieved. The reaction mixture was irradiated with microwaves (Anton Parr Monowave 300 reactor) at 120C for 10-25min. On cooling, the mixture was diluted with DCM (41mL), and filtered over celite. Then the filtrate was washed with Na2CO3 (ss) and water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the ester. 4.3.6.1 Methyl 3-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate (23) (0075) Alcohol: Methanol. Reaction time: 10min. Yield: 95%. Mp: 208-209C. IR (cm-1): 1730, 1655, 1615, 1510, 1490, 1565. MS (m/z): 232.3. 1H-RMN (300MHz) delta (ppm) (DMSO-d6): 2.79 (t; J=7.01Hz; 2H; CH2); 3.06 (t; J=6.83Hz; 2H; CH2); 3.60 (s; 3H; OCH3); 7.23-7.33 (m; 2H; ArH); 7.48 (t; J=7.99Hz; 1H; ArH), 7.68 (d; J=8.40; 1H; ArH), 12.36 (s.a.; 1H; NH).13C-RMN (75MHz) delta (ppm) (DMSO-d6): 28.0 (CH2); 29.8 (CH2); 51.8 (OCH3); 115.7; 123.6; 128.6; 130.0; 131.9; 132.2; 155.0 (C=N); 160.4 (C=O); 173.4 (CO).

7712-28-9 3-(3-Hydroxyquinoxalin-2-yl)propanoic acid 151480, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Estrin, Dario; Fabian, Lucas; Gomez, Natalia; Moglioni, Albertina; Salvatori, Melina; Taverna Porro, Marisa; Turk, Gabriela; European Journal of Medicinal Chemistry; vol. 188; (2020);,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23088-23-5,Methyl 6-Quinoxalinecarboxylate,as a common compound, the synthetic route is as follows.

23088-23-5, The 6-quinoxalinylcarbonyl chloride used as a starting material was prepared as follows: A 2N aqueous sodium hydroxide solution (7.95 ml) was added to a solution of methyl quinoxaline-6-carboxylate (1 g) in a mixture of methanol (30 ml) and water (5 ml) and the mixture was stirred at ambient temperature for 16 hours. The reaction mixture was evaporated and the residue was dissolved in water. The solution was acidified to pH3.5 by the addition of dilute aqueous hydrochloric acid and extracted with ethyl acetate. The organic extracts were evaporated and the residue was triturated under a mixture of ethyl acetate and isohexane. There was thus obtained quinoxaline-6-carboxylic acid a solid (0.5 g); NMR Spectrum: (DMSOd6) 8.16 (d, 1H), 8.28 (d, 1H), 8.59 (s, 1H), 9.02 (s, 2H).

As the paragraph descriping shows that 23088-23-5 is playing an increasingly important role.

Reference£º
Patent; AstraZeneca AB; US6432949; (2002); B1;,
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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

General procedure: Sodium hydride (349 mg, 0.008792 mol, 1.2 eq) was added to a solution of 2-ethylbutyl 2-cyanoacetate (1.23 g, 0.007326 mol, 1.00 eq) in dry DMF (20 ml) at 0C under inert atmosphere. After 10 minutes, 2,3-dichloroquinoxaline (1.75 g, 0.008792 mol, 1.2 eq) was added and the reacting mixture was stirred overnight at 70C. The solution was cooled to 0C then diluted in sat. H4CI and extracted with DCM . The combined organic layers were dried over MgS0 , filtered and concentrated. Purification by column chromatography on silica gel (0 to 30% AcOEi/liexanes) provided 2-ethylbutyi 2-(3-chloroquinoxalin-2-yl)-2-cyanoacetate as a yellow solid (2.20 g, 74% yield). A solution of (Z)-2-ethylbutyl 2-(3-chloroquinoxalin-2(lH)-ylidene)-2-cyanoacetate (1 eq), piperazine (3 eq) and DIPEA (3 eq) in methanol (0.1M) was stirred at 120C in a microwave for 90 minutes or until completion. The solution was cooled down, diluted in water/DCM followed by extraction with DCM. The combined organic layers were dried over MgS04, filtered, concentrated and purified by column chromatography on silica gel (0 to 100% AcOEt in hexanes) or by reverse phase C18 (5 to 100% CH3CN 0.1% TFA in water 0.1% TFA) to furnish (Z)-2-ethylbutyl 2-cyano-2-(3-(piperazin-l-yl)quinoxalin-2(lH)-ylidene)acetate., 108229-82-9

As the paragraph descriping shows that 108229-82-9 is playing an increasingly important role.

Reference£º
Patent; CORSELLO, Steven M.; GOLUB, Todd R.; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; STEFAN, Eric; HILGRAF, Robert; (158 pag.)WO2018/183936; (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.32601-86-8,2-Chloro-3-methylquinoxaline,as a common compound, the synthetic route is as follows.

32601-86-8, EXAMPLE 7 N-(2-Propenyl)carbamimidothioic acid(3-methyl-2-quinoxalinyl)ester, hydrochloride 2-Chloro-3-methylquinoxaline (5.359 g., 0.03 mole) was dissolved in 75 ml. of acetone, treated with Norit and filtered. The filtrate was added to a solution of 3.485 g. (0.03 mole) of allylthiourea in 50 ml. of acetone while the solution was stirred at room temperature under N2. A precipitate had formed at the end of 2 hours. Stirring was continued for 31/2 hours. The solid that was filtered off was washed with acetone, then ether and dried, to give 6.68 g. (75.6% yield) of product as a pink solid, m.p. 113-114 C. Analysis for: C13 H15 ClN4 S Calculated: C, 52.97; H, 5.13; N, 19.01; Cl, 12.02; S, 10.87. Found: C, 52.78; H, 5.09; N, 19.33; Cl, 12.05; S, 10.77.

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

Reference£º
Patent; American Home Products Corporation; US4349674; (1982); A;,
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