Heterocyclic Building Blocks-quinoxaline

55687-23-5, 6-Fluoroquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

55687-23-5, Intermediate 141: tert-Butyl ?-r2-f7-fluoro-2-oxoquinoxalin-lC2H)- vDethyllpiperidin-4-yl)carbamate andIntermediate 142: tert-Butyl {l-[2-C6-fluoro-2-oxoquinoxalin-lf2H)- yl)ethyl]piperidin-4-yllcarbamateA suspension of a 1:1 mixture of 7-fluoroquinoxalin-2(lH)-one (Intermediate 143) and 6-fluoroquinoxalin-2(lH)-one (Intermediate 144) (1.5 g total, 9.1 mmol) was treated with sodium hydride (60% in oil, 0.44 g, 11.0 mmol) at O0C. The reaction was allowed to stir at room temperature for 2 hours. The reaction mixture was cooled to 0 C and 2-{4-[(tert- butoxycarbonyl)amino]piperidin-l-yl} ethyl methanesulfonate (Intermediate 6, 1.33 mmol/mL, 11.0 mmol), dissolved in dry DMF (5 mL) was added and it was stirred at room temperature overnight. The reaction mixture was diluted with water and with diethyl ether (5x 50 mL). The combined organic phases were dried over sodium sulfate and concentrated to dryness under reduced pressure. Chromatography with hexanes/ acetone (5:1 to 3:1). The higher Rf material was isolated as a mixture of Intermediate 141 with an O-alkylated isomer, which was rechromatographed on silica gel with hexanes/ ethyl acetate (1:3) to give pure Intermediate 141 as a colorless solid, 0.24 g, 14%. Isolation of the lower Rf material from the first column gave 0.38 g (21%) of pure Intermediate 142 as a colorless solid. Intermediate 141:MS QBS): 391 (MH+) for C20H27FN4O31H NMR omegaMSO-D6) delta 1.25-1.38 (m, HH); 1.56-1.68 (m, 2H); 2.01 (t, 2H); 2.50- 2.56 (m, 2H); 2.82-2.93 (m, 2H); 3.16 (s, IH); 4.27 (t, 2H); 6.72 (d, IH); 7.23 (t, IH); 7.50 (d, IH); 7.83-7.91 (m, IH); 8.17 (s, IH). Intermediate 142:MS (ESV 391 (MH+) for C20H27FN4O31H NMR (DMSO-DO’) delta 1.24-1.38 (m, HH); 1.65 (d, 2H); 2.03 (t, 2H); 2.51-2.58 (m, 2H); 2.88 (d, 2H); 3.11-3.26 (m, IH); 4.31 (t, 2H); 6.75 (d, IH); 7.57 (td, IH); 7.63-7.71 (m, 2H); 8.29 (s, IH).

55687-23-5 6-Fluoroquinoxalin-2(1H)-one 12686386, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/134378; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-34-8,6-Bromoquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

To a stirred solution of the compound obtained from Preparation 29 (2 g, 8.89 mmol) in phosphorus oxychloride (15 mL), was added DMF (1 mL). The mixture was stirred at 120C for 1.5 hours then allowed to cool to room temperature. The dark solution was concentrated in vacuo and cautiously quenched with crushed ice. The aqueous suspension was neutralised with 10% potassium carbonate solution and extracted with DCM (2 x 30 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated to give 1.94 g of the title compound as a brown solid.1H-NMR (400 MHz, DMSOd6): delta= 9.02(1 H, s), 8.40(1 H, d), 8.06(1 H, dd), 7.98(1 H, d). LCMS (run time = 2min): R4 = 1.69 min; m/z 243; 245 [M+H]+, 55687-34-8

As the paragraph descriping shows that 55687-34-8 is playing an increasingly important role.

Reference£º
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; PRYDE, David Cameron; TRAN, Thien Duc; WO2011/4276; (2011); A1;,
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6344-72-5, 6-Methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 6-methylquinoxaline (2.0 g, 13.9 mmol), N-bromosuccinimide (3.0 g, 16.9 mmol), and benzoyl peroxide (411 mg, 1.7 mmol) in anhydrous carbon tetrachloride (50 mL) was stirred at reflux for 2 days. Dichloromethane (50 mL) was added after cooling to room temperature. The mixture was extracted with 1 N NaOH (1 x 100 mL) and brine (1 x 100 mL). The organic extract was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-30% EtOAc/hexanes), affording 6- (bromomethyl)quinoxaline (1.10 g, 35% yield)., 6344-72-5

The synthetic route of 6344-72-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
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50998-18-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.50998-18-0,6-Iodoquinoxaline,as a common compound, the synthetic route is as follows.

General procedure: Arene (0.10 mmol, 1.0 equiv), Pd(OAc)2 (2.2 mg, 10 mumol,10 mol%), ligand (15 mol% or 20 mol%), hydrogen phosphate (15 mol% for benzylamine substrate), aryl iodide (0.3 mmol, 3.0 equiv.) and silver acetate (50 mg, 0.30 mmol, 3.0 equiv.) were added into a 2-dram reaction vial. Solvent and (+)-NBE-CO2Me (20 mol% or 50 mol%) were added to the mixture. The vial was flushed with N2 and capped. The reaction mixture was then stirred at the selected temperature for 12-24 h. After cooling to room temperature, the mixture was filtered through Celite and eluted with ethyl acetate. The filtrate was evaporated under reduced pressure. Purification by preparative thin-layer chromatography afforded the desired product.

As the paragraph descriping shows that 50998-18-0 is playing an increasingly important role.

Reference£º
Article; Shi, Hang; Herron, Alastair N.; Shao, Ying; Shao, Qian; Yu, Jin-Quan; Nature; vol. 558; 7711; (2018); p. 581 – 585;,
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67074-63-9, 4-Methyl-3,4-dihydroquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,67074-63-9

24c. 1,2,3,4-tetrahydroquinoxaline To a solution of 24b (300 mg, 1.85 mmol) in THF (2 mL) was added 1N LiAlH4 (10 mL, 10 mmol). The reaction mixture was stirred at rt for 1 h. The reaction mixture was quenched with H2O (1 mL) at 0 C., 15% NaOH (1 mL), followed by H2O (1 mL). The reaction mixture was extracted with EtOAc. The EtOAc was then washed with brine, dried over Na2SO4. The solvent was evaporated under reduced pressure to afford 24c (260 mg, 95%) as white powder. LC-MS ESI m/z 149 [M+H]+.

67074-63-9 4-Methyl-3,4-dihydroquinoxalin-2(1H)-one 12938663, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-34-8,6-Bromoquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

55687-34-8, Compound 39 (600 mg, 2.66 mmol) was added to cold phosphorous oxychloride (4 mL) in portions wise to give a slurry. To the resulting slurry was added drop wise N,N- dimethylaniline (0.4 ml, 2.93 mmol) below 15C. The brick red mixture was refluxed for 15 min, and the resulting dark brown clear solution was then cooled to ambient temperature. It was added to ice cold water (40 mL) , and the mixture was basified slowly with 40% aq. NaOH to pH 8. The solid was collected by filtration, washed with water (2×10 mL) and dried to give the title compound 40 (70%) .

The synthetic route of 55687-34-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANDYOPADHYAY, Anish; SARANGTHEM, Robindro; BARAWKAR, Dinesh; BONAGIRI, Rajesh; KHOSE, Goraksha; SHINDE, Shailesh; (226 pag.)WO2016/199943; (2016); A1;,
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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.

A slurry of 5-cyclopropyl-3-(2,6-dichlorophenyl)-4-(7-azaspiro[3.5]non-1-en-2-yl)isoxazole (25 mg, 0.07 mmol, synthesis described in General Method A), 6-bromo-2-chloroquinoxaline (19.5 mg, 0.08 mmol) and Cs2CO3 (43.4 mg, 0.13 mmol) in dioxane (0.3 mL) was degassed by bubbling nitrogen through the mixture for 5 minutes. Chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (RuPhos-Pd-G2) (2.59 mg, 3.33 mumol) was added and the reaction mixture was sealed and heated to 90C. for 6 hours. The crude reaction mixture purified directly by flash chromatography on SiO2 (0-100% EtOAc/hexanes, Isco 12 g column) to yield 4-(7-(6-bromoquinoxalin-2-yl)-7-azaspiro[3.5]non-1-en-2-yl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole (26 mg, 0.04 mmol, 64% yield) as a gum. 1H NMR (400 MHz, CDCl3) delta 8.57 (s, 1H), 8.03 (d, J=2.2 Hz, 1H), 7.64 (dd, J=8.8, 2.2 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.46-7.42 (m, 2H), 7.40-7.34 (m, 1H), 5.80 (s, 1H), 3.94 (dt, J=13.5, 5.1Hz, 2H), 3.66-3.50 (m, 2H), 2.44 (s, 2H), 2.21 (tt, J=8.4, 5.1Hz, 1H), 1.76 (t, J=5.6 Hz, 4H), 1.36-1.30 (m, 2H), 1.22-1.15 (m, 2H)., 55687-02-0

Big data shows that 55687-02-0 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; Carpenter, Joseph E.; Huang, Yanting; Wang, Ying; Wu, Gang; (137 pag.)US2019/127362; (2019); A1;,
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49679-45-0, Ethyl 3-chloroquinoxaline-2-carboxylate is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 10 2-(Aminoiminomethylthio)-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride 2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (9.5 g., 0.04 mole) and 3.052 g. (0.04 mole) of thiourea were dissolved in 200 ml. of acetone. The solution was boiled in an open flask for 11/2 hours during which acetone was added to maintain the volume at 200 ml. The reaction mixture was cooled and the solid was collected by filtration to give 7.8 g. of crude product. Recrystallization from methanol-acetone afforded 3.55 g. of off-white solid, over wide range dec. Analysis for: C12 H13 ClN4 O2 S Calculated: C, 46.08; H, 4.19; N, 17.91; Cl, 11.33; S, 10.25. Found: C, 46.01; H, 4.13; N, 17.85; Cl, 11.38; S, 10.32. An additional 4.05 g. of product was recovered from the reaction mixture to give a total yield of 7.60 g. (59.3%). Found: C, 46.06; H, 4.14; N, 17.79; Cl, 11.38; S, 10.37

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

Reference£º
Patent; American Home Products Corporation; US4349674; (1982); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108229-82-9,6-Bromo-2,3-dichloroquinoxaline,as a common compound, the synthetic route is as follows.

108229-82-9, To a solution of compound 1 (0.28 g, 1 mmol) in absolute ethanol (50 mL), hydrazine hydrate90% (0.07 mL, 1.5 mmol) was added and the reaction mixture was stirred in an ice bath at 0 C for 2 h.After completion of the reaction, the precipitate that formed was filtered, dried and the crude productwas further purified by a silica gel column chromatography (chloroform) to give the product. Yield:61%; (red-brown powder): mp 201-203 C; IR (KBr) max in cm1: 3415, 3250, 3146 (NH2, NH), 1598(C=N); 1H-NMR (DMSO-d6): 5.00 (s, br, 2H, NH2; exchangeable with D2O), 7.37-7.79 (m, 3H, Ar-H),9.16 (s, br, 1H, NH; exchangeable with D2O); 13C-NMR (DMSO-d6): 124.68, 129.67, 130.02, 134.78,138.98, 140.60 (6Ar-C), 145.22, 145.85, (2C=N); MS (m/z), 64 (M+ C4H4BrClN3; 100%), 272 (M+; 5%),273 (M+ + 1; 21%), 274 (M+ + 2; 17%), 275 (M+ + 3; 3%), 276 (M+ + 4; 5%). Anal. Calcd. for C8H6BrClN4(273.52): C, 35.13; H, 2.21; N, 20.48%. Found: C, 34.97; H, 2.45; N, 20.34%.

The synthetic route of 108229-82-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Al-Marhabi, Aisha R.; Abbas, Hebat-Allah S.; Ammar, Yousry A.; Molecules; vol. 20; 11; (2015); p. 19805 – 19822;,
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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

The compound [IILA2-3] is formed by coupling 5- [1-amino-2- (3-fluorophenyl)- ethyl]-3- (3-methyl-but-2-enyl)-dihydrofuran-2-one, tosylate salt, (IVa2-2) and quinoxaline-2-carboxylic acid or quinoxaline-2-carbonylchloride as shown in step 3 of Scheme 1. This coupling reaction is generally conducted at a temperature from [ABOUT-30C] to about [80C,] preferably from about [0C] to about [25C.] The coupling reaction may occur with a coupling reagent that activates the acid functionality. Exemplary coupling reagents include dicyclohexylcarbodiimide/hydroxybenzotriazole (DCC/HBT), N-3-dimethylaminopropyl-N’-ethylcarbodiimide (EDC/HBT), [2-ETHYOXY-1-] ethoxycarbonyl-1, 2-dihydroquinoline (EEDQ), carbonyl diimidazole (CDI)/dimethylaminopyridine (DMAP), and diethylphosphorylcyanide. The coupling is conducted in an inert solvent, preferably an aprotic solvent, such as [ACETONITRILE,] [DICHLOROMETHANE,] chloroform, or N, N-dimethylformamide. One preferred solvent is methylene chloride. In one embodiment, quinoxaline acid is combined with methylene chloride, oxalyl chloride and a catalytic amount of N, N-dimethylformamide to form an acid chloride complex. The compound IVa2-2 is added to the acid chloride complex followed by triethylamine at a temperature from about [0C] to about [25C] to form the compound [ILLA2-3.]

879-65-2 2-Quinoxalinecarboxylic acid 96695, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER PRODUCTS INC.; WO2004/14875; (2004); A1;,
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