Heterocyclic Building Blocks-quinoxaline

53967-21-8, 6-(Bromomethyl)quinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,53967-21-8

The light reddish solution of 6-bromomethyl-quinoxaline was used to prepare 6-hydroxymethyl-quinoxaline as shown in the examples below.

The synthetic route of 53967-21-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Air Products and Chemicals, Inc.; US6548670; (2003); B1;,
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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.,55687-02-0

To a stirred solution of tert-butyl (2S)-2-[5-(6-bromopyridin-3-yl)-1 H-imidazol-2-yl]pyrrolidine-1 -carboxylate (1.5 g, 3.8 mmol), obtained from Preparation 55, in dry 1 ,4-dioxane (25 ml_) was added hexamethylditin (1.25 g, 3.8 mmol), followed by Pd(PPh3)4 (1.1 g, 0.95 mmol). The reaction mixture was degassed, put under nitrogen three times and then heated at reflux for 2 hours. The reaction mixture was then allowed to cool to room temperature and diluted with ethyl acetate (50 ml_). The organic phase was washed with saturated aqueous ammonium chloride solution (50 ml_), water (50 ml_) and brine (50 ml_). The organic portion was then dried over sodium sulphate and evaporated. The residue was then dissolved in DMF (25 ml_). 6-Bromo-2- chloroquinoxaline (0.93 g, 3.8 mmol) was added, followed by cesium fluoride (1.1 g, 6.9 mmol), copper (I) chloride (0.34 g, 13.8 mmol) and Pd(PPh3)4 (1.0 g, 0.86 mmol). The reaction mixture was degassed three times and then heated to 1100C for 5 hours. It was allowed to cool to room temperature and then was poured into ethyl acetate (200 ml_). The resulting suspension was washed with 0.880 ammonia solution (200 ml_). The aqueous layer was extracted with more ethyl acetate (2 x 50 ml_) and the combined organic layers were dried over sodium sulphate and evaporated. The crude product was purified by column chromatography (ethyl acetate: heptane 1 :3 to 1 :1 ) to afford the title compound as a yellow solid (0.73 g).1H NMR (400 MHz, DMSOd6): delta= 12.16 (1 H, m), 9.90 (1 H, s), 9.19 (1 H, d), 8.51 (1 H, d), 8.38 (1 H, d), 8.34 (1 H, dd), 8.11 (1 H, d), 8.03 (1 H, dd), 7.82 (1 H, m), 4.85 (1 H, m), 3.56 (1 H, m), 3.38 (1 H, m), 2.24 (2H, m), 1.94 (2H, m), 1.30 (9H, br s, 9H).

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

Reference£º
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; PRYDE, David Cameron; TRAN, Thien Duc; WO2011/4276; (2011); A1;,
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83570-42-7, 1-(Quinoxalin-6-yl)ethanone is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,83570-42-7

A mixture of quinoxaline-6-carboxylic acid (2 g, 11.49 mmol) and thionyl chloride (30 mL) was stirred at reflux for 2 hours. The reaction mixture was concentrated to dryness using a rotary evaporator to afford quinoxaline-6- EPO carboxylic acid chloride (crude quantitative). A solution of the above acid chloride (11.49 mmol) in DCM (50 mL) and pyridine (20 mL) was mixed with N,O-dimethyl hydroxylamine HCI salt (2.24 g, 23 mmol) and stirred at room temperature for 12 hours. The reaction was quenched by adding aqueous HCI (50 mL, 1 N), extracted with DCM (3×100 mL), concentrated using a rotary evaporator. The residue was further purified by column (Sitheta2, Hexanes/EtOAc = 1 :3) to yield quinoxaline-6-carboxylic acid methoxy-methyl-amide (2 g, 80%). To a solution of the above Weinreb amide (2.0 g, 9.2 mmol) in THF (30 mL) at O0C was added methyl magnesium bromide (3.9 mL, 11.6 mmol). The reaction mixture was stirred at O0C for 2 hours and then 1 hour at room temperature, quenched by adding aqueous HCI (20 mL, 1 N), extracted with DCM (3×100 mL), concentrated using a rotary evaporator. The residue was further-purified by column (SiO2, Hexanes/EtOAc = 1 :3) to yield 6-acetylquinoxaline (1.17 g, 74%). A solution of 2- chloronicotinic acid ethyl ester (5.0 g, 27 mmol) in MeOH (25 mL) was mixed with sodium methoxide (25.6 mL, 112.5 mmol) and stirred at reflux for 12 hours. The reaction was quenched by adding water (100 mL), extracted with DCM (3×100 mL), concentrated using a rotary evaporator to afford 2-methoxynicotinic acid methyl ester (3.2 g, 71%). A solution of 6-acetylquinoxaline (0.62 g, 3.6 mmol), 2- methoxynicotinic acid methyl ester (0.64 g, 3.8 mmol), and sodium hydride (0.46 g, 11.4 mmol) in THF (100 mL) was stirred at room temperature for 16 hours. The reaction was quenched by adding water (100 mL) and AcOH (20 mL), extracted with dichloromethane (3×100 mL), and concentrated using a rotary evaporator. The residue was re-dissolved in DCM (5 mL) and MeOH (3 mL) and was diluted with Hexanes (50 mL). The solid was removed by filtration and the filtrate was concentrated to afford the diketo compound (0.7 g, 60%). A solution of the above diketone (0.4 g, 1.3 mmol) in AcOH (50 mL) and sulfuric acid (cone, 15 drops) was stirred at reflux for 1 hour. Most of the solvent was removed using a rotary evaporator. The residue was re-dissolved in MeOH and neutralized with potassium carbonate to pH = 8. The solid residue was removed by filtration, washed with MeOH and DCM. The filtrate was extracted with CH2CI2 (3×100 mL) and concentrated using a rotary evaporator. The solid residue was purified by column (SiO2, Hexanes/EtOAc/MeOH = 2:2:1) to afford 2-(quinoxalin-6-yl)-4H- EPO pyrano[2,3-b]pyridin-4-one (90 mg, 24%); MS (ES) m/z: 276 (M+1 ); MP 272.3- 274.80C

The synthetic route of 83570-42-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
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879-65-2, 2-Quinoxalinecarboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,879-65-2

Example 108; 4-(4-Fluoro-benzyl)-1-(quinoxaline-2-carbonyl)-piperidine-4-carbonitrile To a stirred solution of Quinoxaline-2-carboxylic acid (100 mg, 0.57 mmol) in DMF was added DIPEA (0.3 ml, 0.72 mmol), EDCI (220 mg, 1.15 mmol), and HOBT (116 mg, 0.86 mmol) at 0 C. The reaction mixture was stirred for half an hour atroom temperature and was added 4-(4-Fluoro-benzyl)-piperidine-4-carbonitrile (125 mg, 0.57 mmol). The reaction mixture was stirred overnight atroom temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated under reduced pressure. Thus obtained crude was purified with column chromatography (Si-gel, 0.5% MeOH-DCM) to afford 110 mg (51.4%) of 4-(4-Fluoro-benzyl)-1-(quinoxaline-2-carbonyl)-piperidine-4-carbonitrile. LC/MS [M+H]+: 375.4. 11H-NMR (400 MHz, DMSO-d6) delta (ppm): 9.1 (s, 1H), 8.17-7.94 (m, 4H), 7.36 (t, 2H), 7.17 (t, 2H), 4.64 (d, 1H), 4.0 (d, 1H), 3.27 (m, 1H), 2.99 (m, 3H), 1.93 (m, 1H), 1.79 (m, 3H). HPLC: 97.1%

The synthetic route of 879-65-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KHAMRAI, Uttam; Ronsheim, Matthew; Karak, Sumit Kumar; US2010/152160; (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.91-19-0,Quinoxaline,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.

As the paragraph descriping shows that 91-19-0 is playing an increasingly important role.

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.83570-42-7,1-(Quinoxalin-6-yl)ethanone,as a common compound, the synthetic route is as follows.

To a solution of 2-chlorothiazole (1 g, 8.4 mmol) in dry THF (10 mL) at -78 C under N2 was added n-BuLi (3.5 mL, 9.2 mmol) dropwise and the mixture stirred for 1 h. A solution of Compound 3 (1.3 g, 7.6 mmol) in dry THF (5 mL) was added dropwise to the reaction mixture at -78 C. The resulting solution was slowly warm to RT. The reaction was diluted with NH4C1 solution and extracted with EA. The organic extracts were concentrated to give a crude oil. The crude product was purified by silica gel chromatography to afford Example 1 (55 mg, 2 %) and Compound 4 (1.6 g, 76.2 %).Example 1: 1HNMR (CDC13, 300 MHz) oe: 2.0-2.2 (s, 3 H), 4.1-4.2 (s, 1 H), 7.3-7.4 (s,1 H), 7.8-7.9 (d, 1 H), 8.0-8.1 (d, 1 H), 8.2-8.3 (s, 1 H), 8.8 (m, 1 H), 9.0 (s, 1 H), 9.3-9.4(m, 1 H).LC-MS: mlz=375.1 (M+1) .

As the paragraph descriping shows that 83570-42-7 is playing an increasingly important role.

Reference£º
Patent; FORGE LIFE SCIENCE, LLC; REMISZEWSKI, Stacy; KOYUNCU, Emre; SUN, Qun; CHIANG, Lillian; (98 pag.)WO2016/77232; (2016); A2;,
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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.

EXAMPLE 14 2-[(1-Methylethylamino)(1-methylethylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride 2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (4.73 g., 0.02 mole) and 3.206 g. (0.02 mole) of 1,3-diisopropylthiourea were dissolved in 90 ml. of acetone and 10 ml. of acetic acid. The solution was heated on the steambath for 23/4 hours and filtered hot. The solvent in the filtrate was evaporated and the residue was triturated with ether until it solidified. Filtration gave 2.33 g. of crude product. Recrystallized from acetone-ether it afforded 1.28 g. (16.1%) of a yellow solid, m.p. 148-149 C. (dec). Analysis for: C18 H25 ClN4 O2 S Calculated: C, 54.47; H, 6.35; N, 14.12; Cl, 8.93; S, 8.08. Found: C, 54.44; H, 6.18; N, 14.19; Cl, 8.96; S, 8.25.

49679-45-0 Ethyl 3-chloroquinoxaline-2-carboxylate 12283436, aquinoxaline compound, is more and more widely used in various.

Reference£º
Patent; American Home Products Corporation; US4349674; (1982); A;,
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55686-94-7, 2-Chloro-7-nitroquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-Chloro-7-nitroquinoxaline (27.8g, 133mmol), 1 -methyl-4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazole (30.4g, 146mmol), 2M Na2C03 aqueous solution (66.3ml_, 133mmol) in ethylene glycol dimethyl ether (330ml_) were degassed with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium (0) (1.5g, 1 .33mmol) was added and the reaction mixture was heated at 100C for 7 hours. The reaction was poured into water. The precipitate was filtered off, taken-up with EtOAc, then filtered and dried under vacuum to give 31.4g (93%) of intermediate 4 (yellow solid). MP=231 C (DSC).

The synthetic route of 55686-94-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; SAXTY, Gordon; MURRAY, Christopher William; BERDINI, Valerio; BESONG, Gilbert Ebai; HAMLETT, Christopher Charles Frederick; JOHNSON, Christopher Norbert; WOODHEAD, Steven John; READER, Michael; REES, David Charles; MEVELLEC, Laurence Anne; ANGIBAUD, Patrick Rene; FREYNE, Eddy Jean Edgard; GOVAERTS, Tom Cornelis Hortense; WEERTS, Johan Erwin Edmond; PERERA, Timothy Pietro Suren; GILISSEN, Ronaldus Arnodus Hendrika Joseph; WROBLOWSKI, Berthold; LACRAMPE, Jean Fernand Armand; PAPANIKOS, Alexandra; QUEROLLE, Oliver Alexis Georges; PASQUIER, Elisabeth Therese Jeanne; PILATTE, Isabelle Noelle Constance; BONNET, Pascal Ghislain Andre; EMBRECHTS, Werner Constant Johan; AKKARI, Rhalid; MEERPOEL, Lieven; WO2011/135376; (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.1204-75-7,3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid,as a common compound, the synthetic route is as follows.

The resulting compound (184 mg, 0.500 mmol) was condensed with 3-hydroxyquinoxaline-2-carboxylic acid (98.0 mg, 0.500 mmol) to afford the desired title compound (115 mg, 46%) as a pale yellow solid. 1H-NMR (DMSO-d6, 400 MHz) delta: 12.85 (1H, brs), 9.71 (1H, brs), 7.88 (1H, dd, J=7.8 Hz, 7.4 Hz), 7.65 (1H, dd, J=7.8 Hz, 7.8 Hz), 7.40 (1H, d, J=7.4 Hz), 7.38 (1H, d, J=7.8 Hz), 7.30 (2H, d, J=9.0 Hz), 7.11 (2H, dd, J=9.0 Hz, 3.8 Hz), 5.03 (1H, m), 4.69 (1H, m), 4.04-3.72 (2H, m), 3.56-3.19 (2H, m), 2.08-1.86 (2H, m), 1.75-1.48 (2H, m), 1.32 (3H, d, J=6.6 Hz). IR (KBr) cm-1: 2945, 1685, 1640, 1620, 1505, 1240. MS (ESI, m/z): 505 (M+H)+. HRMS (ESI, m/z): 505.1686 (Calcd for C24H24F3N4O5: 505.1699).

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;,
Quinoxaline – Wikipedia
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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.

General procedure: To ethyl 3-chloroquinoxaline-2-carboxylate 1 (1 g, 4.22 mmol),appropriate acetylene derivative (3.33 mmol, 1.5 eq.) in ethanol(15 mL) was added in a two-necked flask containing triethylamine(1.4 mL, 10 mmol), Pd/C (45 mg, 0.42 mmol), triphenylphosphine(110 mg, 0.42 mmol), and CuI (50 mg, 0.26 mmol). The reaction mixture was stirred at 60 C for 5 h. After cooling, the mixture wasfiltered with celite and the filtrate diluted with dichloromethane,washed with H2O (3 x 40 mL) and dried over MgSO4. After evaporation,the crude product was purified by silica gel chromatography(CH2Cl2).

49679-45-0 Ethyl 3-chloroquinoxaline-2-carboxylate 12283436, aquinoxaline compound, is more and more widely used in various.

Reference£º
Article; Hajri, Majdi; Esteve, Marie-Anne; Khoumeri, Omar; Abderrahim, Raoudha; Terme, Thierry; Montana, Marc; Vanelle, Patrice; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 959 – 966;,
Quinoxaline – Wikipedia
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