Heterocyclic Building Blocks-quinoxaline

49679-45-0,49679-45-0, Ethyl 3-chloroquinoxaline-2-carboxylate is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(1B) Method B: A suspension of ethyl 3-chloroquinoxaline-2-carboxylate (11.5 g, 48.6 mmol), trimethylboroxine (6.06 g, 48.6 mmol), [1,1′-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 colorless crystals (8.36 g, 80%). mp 74-75 C. MS (APCI): m/z 217 (M+H).

The synthetic route of 49679-45-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); A1;,
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80636-30-2, 3,3-Dimethyl-3,4-dihydroquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 8; (7J?)-2-r(3,3-Dimethyl-2-oxo-3,4-dihydroquinoxalin-lf2H)-yl)methyl1-3′-methyl-6.8-dihvdro- 2’H,5’H-spiro[cvclopenta(g1quinoline-7,4′-imidazolidine1-2′,5′-dione; To a solution of 3,3-dimethy~3,4-dihydroquinoxalm-2(lH)-one (56 mg, 0.32 mmol) in DMF (1 mL) at ambient temperature was added sodium hydride (13 mg, 0.32 mmol, 60% dispersion in mineral oil). The resulting mixture was stirred for 20 min, then (i?)-2- (chloromethy^-S’-methyl-jS-dihydro-Z’HjS’H-spirotcyclopentafgJquinoline-T^’-imidazolidine]- 2.,5′-dione (20 mg, 0.063 mmol, described in Intermediate 18) was added and the resulting mixture was stirred at ambient temperature for 1 h. The reaction mixture was purified directly by HPLC using a reversed phase Cl 8 column and eluting with a gradient of H2theta:CH3CN:CF3Ctheta2H – 90:10:0.1 to 5:95:0.1. The pure, product-containing fractions were combined and concentrated to give the title compound as the trifluoroacetate salt. MS: m/z = 456 (M + 1). HRMS: m/z = 456.2033; calculated m/z = 456.2030 for C26H26N5O3., 80636-30-2

The synthetic route of 80636-30-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP &; DOHME CORP.; STUMP, Craig, A.; QUIGLEY, Amy, G.; THEBERGE, Cory, R.; WOOD, Michael, R.; WO2010/107605; (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.1233318-23-4,Methyl 2-(quinoxalin-6-yl)acetate,as a common compound, the synthetic route is as follows.

To dimethyl carbonate (30 mL) cooled at 0 was added potassium tert-butanolate (3.8 g, 34.12 mmol) in portions. The resultant mixture was stirred at 0 for 1 hour. Methyl 2- (quinoxalin-6-yl) acetate (2.3 g, 11.37 mmol) was added. The resultant mixture was slowly warmed up to room temperature and stirred for 1 hour. The reaction mixture was heated to 90 and stirred for 1.5 hours. After cooling to room temperature, the mixture was diluted with EtOAc (150 mL) , washed with saturated NH4Cl (80 mL) and brine (50 mL) , dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column (petroleum ether/ethyl acetate3: 1) to obtain dimethyl 2- (quinoxalin-6-yl) malonate (2.0 g) as a yellow solid. 1H NMR (CHLOROFORM-d) : delta 8.89 (s, 2H) , 8.10 -8.19 (m, 2H) , 7.91 (dd, J 8.7, 2.0 Hz, 1H) , 4.95 (s, 1H) , 3.82 (s, 6H) . LC-MS: m/z 261.1 (M+H) +., 1233318-23-4

As the paragraph descriping shows that 1233318-23-4 is playing an increasingly important role.

Reference£º
Patent; AGIOS PHARMACEUTICALS, INC.; TRAVINS, Jeremy, M.; KONTEATIS, Zenon, D.; SUI, Zhihua; YE, Zhixiong; (199 pag.)WO2018/39972; (2018); A1;,
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6298-37-9, Quinoxalin-6-amine is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6298-37-9, To a solution of 35C enantiomer 1 (0.0251 g, 0.078 mmol) in THF (1.205 ml) was added 4-nitrophenyl carbonochloridate (0.017 g, 0.082 mmol). The reaction was stirred at rt for 30 min. To this reaction were added quinoxalin-6-amine (0.034 g, 0.235 mmol) and triethylamine (0.033 ml, 0.235 mmol). The reaction was heated at 50 C overnight, then allowed to cool to RT. The reaction was diluted with H20 and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered and concentrated to give 35D as a brown residue. The crude material was used without further purification.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; CHEN, Bin; CHEN, Libing; SHAN, Weifang; WO2014/150646; (2014); A1;,
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50998-17-9, 6-Bromoquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,50998-17-9

EXAMPLE 622,5-Dimethyl-5-[3-(quinoxalin-6-yl)phenyl1tetrahydrofuran-2-ol6-Bromoquinoxaline (3.14 g, 15 mmol) was dissolved in DME/water (9:1, 500 niL), and 3-acetylphenylboronic acid (2.5 g, 15 mmol), cesium carbonate (9.75 g, 30 mmol) and Pd(PPh3 )4 (870 mg, 0.75 mmol) were added. The mixture was heated to 1100C for 18 h. After cooling, the mixture was partitioned between EtOAc and water (100 mL each), and the organic phase concentrated in vacuo. The residue was triturated with diethyl ether (50 mL) to give l-[3-(quinoxalin-6-yl)phenyl]ethanone (3.8 g, >95%). LCMS (ES+) 249.2 (M+H)+, RT 3.04 minutes. A sample of this material (500 mg, 2 mmol) was dissolved in THF (4 mL), and cooled to O0C. But-l-en-4-ylmagnesium bromide (0.5M in THF, 4 mL, 2 mmol) was added and the mixture allowed to warm to room temperature. After stirring for 2 h, water (2 mL) was added. The organic phase was passed though a silica plug and concentrated in vacuo. The residue was dissolved in DCM (3 mL). 7V-Bromosuccinimide (146 mg, 0.9 mmol) was added and the mixture stirred at room temperature for 18 h. The mixture was partitioned between DCM (5 mL) and saturated sodium hydrogencarbonate solution (5 mL). The organic phase was passed through a silica plug and the filtrate concentrated in vacuo. The residue was dissolved in MeOH (3 mL). Sodium methoxide (200 mg) was added and the mixture was stirred at 600C for 3 days. The mixture was neutralized to pH 7.0 with IM hydrochloric acid and then concentrated in vacuo. The residue was purified by preparative HPLC to isolate the title compound (5 mg, 2:1 mixture of cis:trans isomers). deltaH (CDCl3) 8.89 (d, IH), 8.86 (d, IH), 8.32 (m, IH), 8.20 (m, IH), 8.08 (m, IH), 7.84 (m, IH), 7.62 (m, IH), 7.50 (m, 2H), 2.10-2.58 (m, 4H), 2.11 (s, 3H), 1.56-1.72 (m, 4H). LCMS (ES+) 321.3 (M+H)+, RT 2.93 minutes.

The synthetic route of 50998-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
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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.

(3) To a solution of 4-chloro-2-(hydroxymethyl)-6-pyrrolidin-1-ylpyrimidine (1.00 g, 4.68 mmol) and 2-chloro-3-methylquinoxaline (1.25 g, 7.02 mmol) in N,N-dimethylformamide (10 mL) and tetrahydrofuran (20 mL) was added sodium hydride (60% dispersion in mineral oil, 281 mg, 7.02 mmol) at 0 C. The reaction mixture was stirred for 2 hour at room temperature, and then poured into cold water. The mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic layer was dried over magnesium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give 4-chloro-2-{[(3-methylquinoxalin-2-yl)oxy]methyl}-6-pyrrolidin-1-ylpyrimidine as red powder (1.67 g, quant.). mp 136-140 C. MS (APCI): m/z 356/358 (M+H).

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; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); 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.

A suspension of 3-chloroquinoxaline-2-carboxylate (86.0 g, 363 mmol), trimethylboroxine (22.8 g, 0.182 mmol), [1,1 ‘- bis(diphenylphosphino) ferrocene] dichloropalladium(II) (8.90 g, 11.0 mmol), and potassium carbonate (100 g, 727 mmol) in 1,4-dioxane (726 mL) was heated at 115 C for 4 h. And then trimethylboroxine (22.8 g, 0.182 mmol) was added again and heated at same temperature for 2 h. After being cooled to ambient temperature, the reaction mixture was diluted with ethyl acetate (700 mL) and filtrated through celite with ethyl acetate (1000 mL). The filtrate was combined and concentrated in vacuo. The residue was purified by silica gel column chromatography (silica gel 900 g, hexane: ethyl acetate = 9: 1 to 17:3) followed by recrystallization from cold hexane to give ethyl 3- methylquinoxaline-2-carboxylate. MS (APCI): m/z 217 (M+H)., 49679-45-0

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

Reference£º
Patent; MITSUBISHI TANABE PHARMA CORPORATION; KAWANISHI, Eiji; HONGU, Mitsuya; TANAKA, Yoshihito; WO2011/105628; (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.1593-08-4,2-Formylquinoxaline,as a common compound, the synthetic route is as follows.

Quinoxaline-2-carbaldehyde 626 (1.58 g, 10 mmol) was dissolved in EtOH (150 mL) and 1, 4-xylylenediamine (0.63 g, 4.6 mmol) was then added and mixture was stirred at 75 C for 3 h. The mixture was then cooled to room temp and the precipitate was filtered and washed with EtOH (¡Á3) to give the intermediate diimine as an off-white solid (1.82 g, 95%); mp = 185-186 C. The diimine (1.81 g, 4.3 mmol) was dissolved in MeOH (50 mL) and then cooled over an ice bath. Sodium cyanoborohydride (273 mg, 4.3 mmol) and acetic acid (4 mL) were added to the cooled solution and the suspended solid dissolved gradually whilst the mixture was stirred at room temp for 3 h. The volatile components were evaporated under diminished pressure. Ethyl acetate was then added to residue and this was then washed with aq NaHCO3. The aq layer was further extracted with EtOAc (3 ¡Á 10 mL). The combined organic layer was dried (MgSO4), filtered and the solvent was removed. Chromatography of the residue (EtOAc-MeOH, 2:1) gave 7 as a dark red solid (1.31 g, 72%); mp = 116-117 C; 1H NMR (CDCl3, 500 MHz): delta = 8.88 (s, 2H), 8.05-8.09 (m, 4H), 7.70-7.76 (m, 4H), 7.35 (s, 4H), 4.16 (s, 4H), 3.92 (s, 4H), 2.23 (s, 2H, NH); 13C NMR (125 MHz, CDCl3) delta 154.9 (C), 145.3, 141.9, 141.8 (each CH), 138.7 (C), 130.0, 129.3, 129.2, 129.0, 128.4 (each CH), 53.4, 52.8 (each CH2). HRMS (ESI): Found 443.1960 [M+Na]+, C26H24N6Na requires 443.1968.

1593-08-4, 1593-08-4 2-Formylquinoxaline 594088, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Jarikote, Dilip V.; Li, Wei; Jiang, Tao; Eriksson, Leif A.; Murphy, Paul V.; Bioorganic and Medicinal Chemistry; vol. 19; 2; (2011); p. 826 – 835;,
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879-65-2,879-65-2, 2-Quinoxalinecarboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 67QUINOXALINE-2-CARBOXYLIC ACID [(R)-1-(2-FLUORO-4-METHANESULFONYLAMINO-5-METHYLPHENYL)ETHYL]AMIDE To a stirred solution of quinoxaline-2-carboxylic acid (26 mg, 0.15 mmol), N-[4-((R)-1-aminoethyl)-5-fluoro-2-methylphenyl]methanesulfonamide hydrochloride (35 mg, 0.12 mmol), and N,N,N’,N’-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (56 mg, 0.15 mmol) in N,N-dimethylformamide (0.5 mL) was added N,N-diisopropylethylamine (80 mg, 0.6 mmol). A catalytic amount of DMAP was added, and the reaction was stirred at room temperature for 16 hours. The reaction mixture was concentrated down to a solid. The crude product was suspended in MeOH and filtered, and the filtrate purified by HPLC to give the title compound (25.0 mg, 49%) as an off-white solid. m/z=403.1 (M+1), r.t. 2.83 min. 1H NMR (400 MHz; d6-DMSO) delta 9.43 (1H, s), 9.39 (1H, d), 8.30-8.26 (1H, m), 8.22-8.18 (1H, m), 8.03-7.97 (2H, m), 7.45 (1H, d), 7.11 (1H, d), 5.49-5.39 (1H, m), 3.02 (3H, s), 2.24 (3H, s), 1.57 (3H, d).

As the paragraph descriping shows that 879-65-2 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; RENOVIS, INC.; US2012/88746; (2012); A1;,
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887590-25-2, tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

887590-25-2, 11.2: trans-4-(5-Hydroxyadamantan-2-ylcarbamoyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester 0.4 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is placed in 8 ml of dichloromethane at 0 C. under nitrogen. 0.69 ml of triethylamine and 0.202 g of triphosgene are added. The mixture is stirred at ambient temperature for 3 h, then 1 ml of dimethylformamide and 0.285 g of trans 4-aminoadamantan-1-ol are added and stirring is maintained for 18 h. The reaction medium is washed with a saturated aqueous sodium hydrogencarbonate solution. The organic phase is dried over magnesium sulphate and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of a dichloromethane/methanol (99/1 to 95/5) mixture. 0.54 g of trans-4-(5-hydroxyadamantan-2-ylcarbamoyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is obtained. M+H+=428

As the paragraph descriping shows that 887590-25-2 is playing an increasingly important role.

Reference£º
Patent; SANOFI-AVENTIS; US2011/9391; (2011); A1;,
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