Heterocyclic Building Blocks-quinoxaline

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;,
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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

2-Bromoquinoxaline 50 (350 mg, 1.67 mmol, 1 eq) was dissolved in EtOAc (16 ml). Octanal (1.05 ml,6.715 mmol, 4 eq) and TMSN3 (0.44 ml, 6.698 mmol, 2 eq) were added. Phi(OCOCF3)2 (1.44 g, 6.698mmol, 2 eq) was added portionwise over 10 min and the mixture turned orange in colour. The mixturewas stirred at room temperature for 2 h. Further TMSN3 (0.44 ml, 6.698 mmol, 2 eq) and Phi(OCOCF3)220 (1.44 g, 6.698 mmol, 2 eq) were added and reaction was stirred for 18 h. Triethylamine (2 ml) was addeddropwise and the mixture was stirred for 15 min. The reaction mixture was concentrated and the crudemixture was purified by silica gel column chromatography (50:1 pentane: EtOAc) to afford product 51 as ayellow solid (259 mg, 61%). Rt = 0.38 (10:1 cyclohexane: EtOAc); m.p. = 43-48 oc; 1H NMR (400 MHz,CDCI3) o 8.16-8.04 (m, 2H), 7.90-7.81 (m, 2H), 3.18 (t, J = 7.5 Hz, 2H), 1.83-1.75 (m, 2H), 1.44-25 1.28 (m, 8H), 0.89 (t, J = 7.0 Hz, 3H); 13C NMR (101 MHz, CDCI3) o 201.5, 149.8, 143.3, 139.6, 134.8,132.6, 131.2, 129.8, 128.61, 40.7, 31.8, 29.3, 29.2, 23.7, 22.8, 14.2; IR (CHCI3) (vmax, cm-1) 3429, 1708,1560; HRMS (ESI) [M + Hf calc 335.0759 for C16H20N20 79Br, found 335.0759., 36856-91-4

The synthetic route of 36856-91-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITY COLLEGE DUBLIN; GUIRY, Patrick; GODSON, Catherine; (148 pag.)WO2018/33642; (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 2-methyl-quinoxaline (1 g, 7 mmol) in 1,4-dioxane (30 ml) was added selenium dioxide (2.3 g, 21 mmol) and the mixture heated to 60C for 2 hours. After cooling the reaction mixture, it was filtered over celite and partitioned between water and ethylacetate. The combined organic phases were successively washed with water (50 ml x 2) and brine (50 ml x 2), dried over anhydrous sodium sulphate and evaporated under vacuo, to afford 0.6 g of the crude title compound as a brown solid, which was used without purification in the next step. ?H NMR (400 MHz, DMSOd6) No. 7.98 – 8.09 (3H, m), 8.21-8.24 (1H, m), 8.28 – 8.31 (lH, m), 10.19 (IH, s).

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

Reference£º
Patent; TORRENT PHARMACEUTICALS LTD; WO2005/97746; (2005); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.49568-68-5,3-Chloroquinoxaline-2-carbaldehyde,as a common compound, the synthetic route is as follows.

0.3 mmol of 3-chloro-quinoxaline-2-carboxaldehyde (57.8 mg), 0.3 mmol of ammonium persulfate (68.5 mg) and 0.09 mmol of copper triflate (32.6 mg) were added to a 15 mL thick-walled pressure-resistant reaction tube. In addition, 3 mL of acetonitrile and 30 muL of water were added as a solvent. Then, magnetic stirring was carried out at 60 C for 6 hours, and two kinds of column chromatography silica gel (100-200 mesh) were added to the obtained reaction liquid, and the solvent was removed by distillation under reduced pressure, and the obtained crude product was separated by silica gel column chromatography. And the volume ratio is 10:1The mixture of petroleum ether and ethyl acetate was eluted as an eluent, and the elution progress was followed by TLC, and the eluate containing the desired product was collected, and the solvent was combined to evaporate the solvent to give the desired product. This material was a white solid with a yield of 70%.

49568-68-5, The synthetic route of 49568-68-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Zhejiang University of Technology; Liu Yunkui; Bao Hanyang; Liu Lianyan; (16 pag.)CN109422700; (2019); 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

Example 21N- (2-Ethy[pheny[)-3-methy[-5-[(3-methy[quinoxa[in-2-y[)amino]- 1 ,2-thiazo[e-4- carboxamide A mixture of 5-amino-N-(2-ethy[pheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide [Intermediate 11(150 mg, 0.57 mmo[, 1.4 eq), 2-ch[oro-3-methy[quinoxa[ine [CASRN: 32601-86-8] (73 mg, 0.41 mmo[, 1.0 eq) and cesium carbonate (307 mg, 0.94 mmo[, 2.3 eq) in 4 mL dioxane/DMF (7/1) was p[aced in a microwave via[ and f[ushed with argon. Then, pa[[adium(II) acetate (9 mg, 0.04 mmo[, 0.1 eq) andXantphos (24 mg, 0.04 mmo[, 0.1 eq) were added. The via[ was capped and the reaction mixture was stirred at an environmenta[ temperature of 110 C overnight. On coo[ing, the reaction mixture was partitioned between dich[oromethane and water. After fi[tration over Ce[ite, the organic phase was separated and concentrated in vacuo. The crude product was purified via preparative HPLC underacidic conditions (co[umn: Chromatorex C18, e[uent: acetonitri[e/ 0.1% aqueous formic acid 20:80 – 95:5). The product fractions obtained were crysta[[ised from diethy[ether to give 3 mg (1.3% yie[d of theory) of the tit[e compound.UPLC-MS (Method 3): R = 1.48 mm; MS (Elneg) m/z = 402 [M-H].1H-NMR (400 MHz, CDC[3): oe [ppm] = 1.31 (t, 3H), 2.73 (q, 2H), 2.85 (s, 3H), 2.89 (s,3H), 7.21-7.29 (m, 1H, partia[[y covered by so[vent signa[), 7.30-7.39 (m, 2H), 7.58 (t, 1H), 7.64-7.74 (m, 2H), 7.87 (d, 1H), 7.97 (d, 1H), 8.05 (d, 1H), 12.45 (s br, 1H)., 32601-86-8

The synthetic route of 32601-86-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (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.6298-37-9,Quinoxalin-6-amine,as a common compound, the synthetic route is as follows.

6298-37-9, [0143] 5-Chloro-2-methoxybenzoic acid (162.0 mg, 0.868 mmol) was dissolved in DCM (5.0 mL), followed by the addition of catalytic amount of DMF (10 .iL) and oxalyl chloride (0.09 mL, 1.042 mmol) respectively. The reaction was allowed to stir at rt for 30 mm, concentrated in vacuo. The residue was re-dissolved in TIIF (5.0 mL), 2,6-lutidine (0.1 mL, 0.868 mmol) and quinoxalin-6-amine (100.0 mg, 0.689 mmol) were added. The mixture was stirred at rt for 18 hours before silica gel was added to quench the reaction. Solvent was evaporated and the resulting residue was purified via silica gel column chromatography to give 5-chloro-2-methoxy- N-(quinoxalin-6-yl)benzamide (85.0 mg, 39% yield). This compound (35.5 mg, 0.113 mmol) was then mixed with pyridinium chloride (360.0 mg). The mixture was heated to 200 C, stirred for 5 minutes and cooled down to rt. The resulting solid was suspended in water and extracted with EtOAc. The organic phase was separated and evaporated. The resulting residue was purified via preparative TLC to yield 5-chloro-2-hydroxy-N-(quinoxalin-6-yl)benzamide 22(10.6 mg, 31% yield). ?H NIvIR (300 MHz, Acetone-d6) 6 8.89 (dd, J= 14.9, 1.8 Hz, 2H), 8.72 (d, J 2.4 Hz, 1H), 8.26 – 8.07 (m, 3H), 7.10 (d, J = 8.8 Hz, 1H). MS (ESI) exact mass calculated for [M+H] (C15H1 1C1N302) requires mlz 300.1, found mlz 299.8

6298-37-9 Quinoxalin-6-amine 0, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; JIN, Shengkan; AUGERI, David, J.; KIMBALL, David, S.; LIU, Peng; TAO, Hanlin; ZENG, Xiangang; (82 pag.)WO2016/81599; (2016); A1;,
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1865-11-8, Methyl quinoxaline-2-carboxylate is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[1500] a solution of compound 356a (2.5 g, 13.29 mmol) in CH3COOC2H5 (60 ml) was added t-BuOK (1.94 g, 17.28 mmol). The mixture was stirred for 0.25 hour at 25¡ãc. The mixture was quenched with H2O (50 ml). The organic layer was separated and the aqueous was extracted with ea (50 ml x 3). The organic phases were combined, dried with anhydrous Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (pe: ea =20/1 to 10/1) to afford compound 356b (2.45 g, 75.48percent yield) as pale yellow solid. 1H NMR (CDCl3, 400 mhz) delta 9.57 – 9.33 (m, 1h), 8.19 – 8.06 (m, 2h), 7.96 – 7.74 (m, 2h), 4.35 – 4.26 (m, 2h), 4.24 – 4.13 (m, 2h), 1.28 – 1.18 (m, 3h).

1865-11-8, As the paragraph descriping shows that 1865-11-8 is playing an increasingly important role.

Reference£º
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); 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, 4.8 6-Bromo-2-hydrazinyl-3-methylquinoxaline (8) To a solution of compound (5, 0.01 mol) in absolute ethanol (50 mL), hydrazine hydrate 90% (0.015 mol) was added and the reaction mixture was refluxed for 10 h (monitored by TLC). After completion of the reaction, the reaction mixture was filtered, dried and crystallized from methanol to give the product. Yield: 86%; (red-brown powder): mp 129-131 C; IR (KBr) numax in cm-1: 3303, 3253, 3144 (NH2, NH), 2920, 2870 (aliphatic C-H), 1596 (C=N); 1H NMR (DMSO-d6, 500 MHz): delta 2.74 (s, 3H, CH3), 4.51 (s, br s, 2H, NH2; exchangeable with D2O), 7.93-8.27 (m, 3H, Ar-H), 9.02 (s, br s, 1H, NH; exchangeable with D2O); 13C NMR (DMSO-d6, 125 MHz): delta 123.33-140.76 (6Ar-C), 147.84, 148.39 (2C=N); MS (m/z), 237 (M+-CH3; 100%), 252 (M+; 40%), 253 (M++1; 10%), 254 (M++2; 38%). Anal. Calcd for C9H9BrN3 (253.10): C, 42.71; H, 3.58; N, 22.14. Found: C, 42.97; H, 3.44; N, 22.32.

The synthetic route of 98416-72-9 has been constantly updated, and we look forward to future research findings.

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.49679-45-0,Ethyl 3-chloroquinoxaline-2-carboxylate,as a common compound, the synthetic route is as follows.

(IB) Method B: A suspension of ethyl 3-chloroquinoxaline-2-carboxylate (11.5 g, 48.6 mmol) prepared by a method recited in J. Chem. Soc. 1945, 622, trimethylboroxine (6.06 g, 48.6 mmol),[l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.98 g, 2.42 mmol), and potassium carbonate (13.4 g, 97.0 mmol) in 1,4-dioxane (162 mL) was heated for 4.5 hour at 115 C. After being cooled to ambient temperature, the reaction mixture was filtrated through celite with ethyl acetate (500 mL). The filtrate was combined and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate = 9:1 to 2:1) followed by recrystallization from ethanol-water (1/4) to give ethyl 3-methylquinoxaline-2-carboxylate as a colorless crystals (8.36 g, 80%). mp 74-75 0C. MS (APCI): m/z 217 (M+H).

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

Reference£º
Patent; MITSUBISHI TANABE PHARMA CORPORATION; MORIMOTO, Hiroshi; SAKAMOTO, Toshiaki; HIMIYAMA, Toshiyuki; KAWANISHI, Eiji; MATSUMURA, Takehiko; WO2010/30027; (2010); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1204-75-7,3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid,as a common compound, the synthetic route is as follows.

General Method 6: Preparation of (2-((3-chlorophenoxy)methyl)piperidin-1-yl)(3-hydroxyquinoxalin-2-yl)methanone (6-5); Step 1: A suspension of 3-hydroxy-2-quinoxaline carboxylic acid 6-1 (1.0 g, 5.26 mmol), thionyl chloride (4.6 mL, 63.1 mmol, 12.0 equiv) and catalytic DMF (50 muL) in 10 mL toluene was heated to 80 C. After 1 h of heating, the reaction mixture was cooled to room temperature and evaporated to dryness to yield 6-2. In a separate flask, 2-piperidine methanol (0.61 g, 5.26 mmol) and triethylamine (0.88 mL, 6.3 mmol, 1.2 equiv) in 10 mL CH2Cl2 was cooled to 0 C. To this mixture was added 6-2 dropwise. The reaction was allowed to stir at room temperature for 1 h after which was diluted with H2O (10 mL), extracted with CH2Cl2 (2¡Á10 mL), dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography (20-40% EtOAc/hexanes) to produce compound 6-3., 1204-75-7

1204-75-7 3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid 71001, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; CHENG, CLIFFORD; SHIPPS, JR., GERALD W.; HUANG, XIAOHUA; HUANG, YING; SHAO, NING; RAO, ASHWIN; PALANI, ANANDAN; ORTH, PETER; VOIGT, JOHANNES H.; HERR, ROBERT J.; ROSSITER, LANA MICHELE; ZENG, QI; SUN, XIANFENG; US2012/122837; (2012); A1;,
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