Downstream synthetic route of 34117-90-3

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

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.

General procerure: A solution of compound 14 or 3 (10 mmol) in pyridine (10 mL) was refluxed for 6 h. After cooling, it was poured on ice/water (200 mL) and acidified with diluted HCl (pH = 6) the product extracted by ethyl acetate (100 ¡Á 3). Solution of ethyl acetate dried over sodium acetate anhydrous (50 g) for 2 h, and then the solid is filtered off. A solution of ethyl acetate is evaporated under reduced pressure and crystals are collected., 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; Galal, Shadia A.; Abdelsamie, Ahmed S.; Tokuda, Harukuni; Suzuki, Nobutaka; Lida, Akira; Elhefnawi, Mahmoud M.; Ramadan, Raghda A.; Atta, Mona H.E.; El Diwani, Hoda I.; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 327 – 340;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Some tips on 34117-90-3

34117-90-3, The synthetic route of 34117-90-3 has been constantly updated, and we look forward to future research findings.

34117-90-3, 3-Chloroquinoxalin-2-amine is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthetic procedure for the preparation of (0): In a 5mL round bottom flask, aminopyrazine (250 mg, 1.3 mmol, 1 eq.), diazo compound (968 mg, 3.48 mmol, 2.5 eq.), Rh2(OAc)4 (61.52 mg, 0.139 mmol 10 mol %), and 3 mL of chlorobenzene were placed. The reaction mixture was heated at 100C for 24 hours. The progress of the reaction was monitored by LCMS. After 24 hours, the reaction reached 100% conversion. The mixture was adsorbed on celite and purified on silica column using 40% EtOAc in Heptane as eluent. Yield, 469 mg, 78.4%

34117-90-3, The synthetic route of 34117-90-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PROMEGA CORPORATION; HALL, Mary; KIRLAND, Thomas; MACHLEIDT, Thomas; SHAKHMIN, Anton; WALKER, Joel, R.; (141 pag.)WO2018/22865; (2018); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Brief introduction of 34117-90-3

As the paragraph descriping shows that 34117-90-3 is playing an increasingly important role.

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.

Step B – Synthesis of Int-21BInt-21 A (1.20 g, 6.7 mmol) was combined with 1-phenyl-3-bromopropane-1,2-dione (1.67 g, 7.4 mmol, prepared as a yellow oil by bromination in CHCl3 at 50 C, followed by chromatography) in THF (10 mL) and ether (15 mL). The mixture was stirred 18 h, concentrated, treated with ethanol (40 mL), heated at 90 C for 72 h, and allowed to cool.Concentration, addition of methanol (10 mL), and filtration gave Int-21B as a brown solid., 34117-90-3

As the paragraph descriping shows that 34117-90-3 is playing an increasingly important role.

Reference£º
Patent; SCHERING CORPORATION; HARRIS, Joel, M.; NEUSTADT, Bernard, R.; STAMFORD, Andrew, W.; WO2011/60207; (2011); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Analyzing the synthesis route of 34117-90-3

34117-90-3, As the paragraph descriping shows that 34117-90-3 is playing an increasingly important role.

34117-90-3, 3-Chloroquinoxalin-2-amine is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : N2-(pentan-3-yl)quinoxaline-2,3-diamine. A thick-walled microwave bottle equipped with a stirbar was charged with 3-chloroquinoxalin-2-amine (1.0 equiv) and 20 volume equivalents of 3-aminopentane. The bottle was fitted with a septum and cap and heated to 120 0C in a microwave for 30 min. The resulting solution was concentrated in vacuo. Flash chromatography (20% – 60% EtOAc/Hexanes) provided the title compound (78%) as a yellow solid. LCMS m/z (APCI) = 231.1 (M+H).

34117-90-3, As the paragraph descriping shows that 34117-90-3 is playing an increasingly important role.

Reference£º
Patent; CYTOKINETICS, INCORPORATED; WO2008/16669; (2008); A2;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Downstream synthetic route of 34117-90-3

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

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.

To a stirred suspension of 2-amino-3-chloroquinoxaline (25.5 g, 141.8 mmol) in water / THF 1 :1 (500 mL), at rt was added 2-bromo-1 ,1 -diethoxyethane (83.8 g, 425.4 mmol) in one portion. After stirring at rt for 1 h, the mixture was heated to reflux for 3 h under stirring and then stirred for an additional 15 h at rt. The pH value of the mixture was adjusted to pH 8 by addition of solid sodium carbonate and the mixture was subsequently extracted with ethyl acetate (3 x 500 ml_) and the combined organic extracts were dried with sodium sulfate. Removal of the solvent yields 4-chloro-imidazo[1 ,2- a]quinoxaline as an orange-white solid (63 g, 93%): 1H-NMR (300 MHz, d6- DMSO): delta =9.05 (d, 1 H), 8.51 (dd, 1 H), 8.1 (dd, 1 H), 7.99 (d, 1 H), 7.89 (td, 1 H), 7.76 (td, 1 H) ppm. UPLC-MS: RT = 0.88 min; m/z 204.6 [MH+]; required MW = 203.6., 34117-90-3

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

Reference£º
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; BADER, Benjamin; BOeMER, Ulf; KREFT, Bertolt; LIENAU, Philip; MARQUARDT, Tobias; PRECHTL, Stefan; SIEMEISTER, Gerhard; WEGSCHEID-GERLACH, Christof; WO2010/124826; (2010); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Some tips on 34117-90-3

The synthetic route of 34117-90-3 has been constantly updated, and we look forward to future research findings.

34117-90-3, 3-Chloroquinoxalin-2-amine is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2; 3-Pyridinemethanol (487 muL, 5.01 mmol) was dissolved in tetrahydrofuran (6.0 mL). To this, 60% sodium hydride (in oil) (200 mg, 5.01 mmol) was added under a nitrogen atmosphere at 0 C. and the mixture was stirred at the same temperature for 15 minutes. To this, 2-amino-3-chloroquinoxaline (300 mg, 1.67 mmol) was added and the mixture was stirred at room temperature for 14 hours. Then, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1). Further, slurry purification was performed using diisopropyl ether, to give 2-amino-3-[(pyridin-3-yl)methoxy]quinoxaline (Compound BA) (383 mg, yield: 91%).ESIMS m/z: 443 (M+H)+; 1H-NMR (300 MHz, CDCl3, delta): 5.20 (br s, 2H), 5.61 (s, 2H), 7.32-7.48 (m, 3H), 7.62 (dd, J=1.5, 8.1 Hz, 1H), 7.72 (dd, J=1.5, 8.1 Hz, 1H), 7.84-7.87 (m, 1H), 8.62 (dd, J=1.5, 4.8 Hz, 1H), 8.80 (d, J=2.2 Hz, 1H), 8.35 (s, 1H)., 34117-90-3

The synthetic route of 34117-90-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Amishiro, Nobuyoshi; Fukuda, Yuichi; Kinpara, Keisuke; Mie, Motoya; Tagaya, Hisashi; Takahashi, Takeshi; US2011/237584; (2011); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

New learning discoveries about 34117-90-3

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

34117-90-3, 3-Chloroquinoxalin-2-amine is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-chloroquinoxalin-2-amine (1.8 g, 10 mmol) and 3, 5 -dimethoxy aniline (4.6 g, 30 mmol, commercially available from Aldrich) are taken up in NMP (4.5 ml) and heated to 1450C in the sealed tube for 3h under N2. When TLC confirms the total consumption of the starting material, the reaction is cooled to rt and treated with EtOAc (4 ml). The first crop of solid is filtered followed by the 2nd crop. The first is recrystallised from CHCl3: EtOAc and the 2nd crop is washed with EtOAc, to afford 1.8 g (60 %) of pure title compound. LC/MS: (ES+): 297.1, (ES-): 295.1.

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

Reference£º
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/23186; (2007); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Downstream synthetic route of 34117-90-3

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

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;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Brief introduction of 34117-90-3

34117-90-3, As the paragraph descriping shows that 34117-90-3 is playing an increasingly important role.

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.

b) Without Pd-catalyst and base – detection of 2-aminoquinoxaline and 3a: Compound 2a (120 mg, 0.65 mmol) was heated with Ph2PH (0.11 mL, 0.64 mmol) for 1.5h at 130 C. Then the resulting blue viscous substance was extracted with diethyl ether to give an olive-green powder (186 mg). The filtrate displayed 31P NMR signals of Ph2PH, Ph4P2 and 3a, signal intensities 31:61:5. An aliquot (90 mg) of the powder was treated with Et2O / aqueous NaOH. Phase separation and drying over CaCl2 gave ca. 50 mg of a viscous yellow mixture of 3a and 2-aminoquinoxaline (13CH signal intensities 1:1), contaminated by small amounts of unconverted Ph2PH and unidentified side products. The 13C NMR data of 3a are in good agreement with those of the pure product. – 2-Aminoquinoxaline: The 1H NMR data are in good agreement with reported values [5]. 13C NMR (CDCl3): d 151.97 (Cq-2), 140.89 (Cq-8a), 137.78 (CH-3), 137.43 (Cq-4a), 130.29 (CH-7), 128.83 (CH-5), 125.88 (CH-8), 125.05 (CH-6); HRMS (ESI in MeOH): Calcd. for 2-aminoquinoxaline (C8H7N3) [M+H+] 146.0713; found: 146.0713; calcd. for 3a (C20H16N3P) [M+H+] 330.1155; found: 330.1158.

34117-90-3, As the paragraph descriping shows that 34117-90-3 is playing an increasingly important role.

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;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Simple exploration of 34117-90-3

34117-90-3, The synthetic route of 34117-90-3 has been constantly updated, and we look forward to future research findings.

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.

Heating a mixture of 2a (495 mg, 2.75 mmol) and Ph2PH (0.48 mL, 2.76 mmol) in the presence of Pd(OAc)2 (0.8 mg, 0.13 mol%) for 2 h at 130C led to a viscous blue-green mass. Extraction of the soluble part with diethyl ether and NMR monitoring in C6D6 identified Ph2P-PPh2, Ph2PCl, 3a and an unknown phosphorus compound (31P signals at d 14.9, 82.2, 12.8 and 5.4 ppm, intensity ratio 84:12:2:2). The insoluble hydrochloride part, 615 mg blue-green powder, was treated with aqueous NaOH/Et2O. The ether phase was dried with Na2SO4 and the ether removed in vacuo to give a brownish-yellow viscous mass (220 mg) with a low content of 3a (relative 31P intensity ca. 20% besides signals of Ph4P2, Ph2PHO and other P compounds). Purification under aerobic conditions by column chromatography on silica gel (ethyl acetate/hexane 95/5%) and removal of solvent gave 180 mg (45%) pale yellow solid 2-aminoquinoxaline. Mp: 156C. 1H NMR (CDCl3) d: 5.03 (vbr s, 2H, NH2), 7.45 (td, 3J = 8.4, 7, 4J = 1.2 Hz, 1H, H-6), 7.61 (td, 3J = 8.4, 7, 4J = 1.2 Hz, 1H, H-7), 7.67 (dd, 3J = 8.4, 4J = 1.2 Hz, 1H, H-8), 7.92 (dd, 3J = 8.4, 4J = 1.2 Hz, 1H, H-5), 8.35 (s, 1H, H-3); these values are in good agreement with the reported data [17]. 13C NMR (CDCl3) d: 125.05 (CH-6), 125.88 (CH-8), 128.83 (CH-5), 137.43 (Cq-4a), 137.78 (CH-3), 130.29 (CH-7), 140.89 (Cq-8a), 151.97 (Cq-2). HRMS (ESI in MeOH): Calc. for C8H7N3 [M+H+] 146.0713; found: 146.0713.

34117-90-3, The synthetic route of 34117-90-3 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;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider