Heterocyclic Building Blocks-quinoxaline

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 solution of 6-bromo-2-chloro-quinoxaline (0.7 g, 1 eq, 2.87 mmol) in THF (6 mL) was added a solution of methyl amine in THF (3 mL) at room temperature. The mixture was stirred at room temperature for 2 h. After completion of the reaction, the volatiles were removed under vacuum and water (20 mL) was added to reaction mixture. The aqueous layer was extracted with ethyl acetate (15 mL x 3). The organic layer was washed with water (20 mL) and brine (20 mL) and then dried over Na2SO4. The organic layer was concentrated under vacuum to afford the crude product.For final purification, column chromatography was used on neutral silica gel of 60-120 mesh size employing a gradient of 3-5% ethyl acetate in hexane to elute the title compound (0.6g, 87%).

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

Reference£º
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert, George; WALKER, David, Winter; WO2010/136755; (2010); A1;,
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91192-32-4,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.91192-32-4,6-Methoxyquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

Step 2: Preparation of 2-chloro-6-methoxyquinoxaline and 3-chloro-6-methoxyquinoxaline A solution of 6-methoxyquinoxalin-2(1H)-one & 7-methoxyquinoxalin-2(1H)-one (3 g, 18.28 mmol) in POCl3 (20 ml) was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The combine organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to afford mixture of regioisomers (3.7 g). 2 g of the above mixture was separated by SFC purification to afford 2-chloro-7-methoxyquinoxaline (0.7 g, 34.7%) and 2-chloro-7-methoxyquinoxaline (0.9 g, 44.6%) as off white solid. 2-chloro-6-methoxyquinoxaline: 1H NMR (400 MHz, DMSO-d6): delta ppm 1H NMR (400 MHz, CDCl3): delta ppm 8.71 (s, 1H), 7.91-7.89 (d, J=8 Hz, 1H), 7.46-7.38 (m, 2H), 3.97 (s, 3H); MS: MS m/z 194.9(M++1).

91192-32-4 6-Methoxyquinoxalin-2(1H)-one 13437707, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.50998-17-9,6-Bromoquinoxaline,as a common compound, the synthetic route is as follows.

50998-17-9, 11k (100 mg, 400 mol), 6-bromoquinoxaline (125 mg, 600 mumol), Bu4NOAc (241 mg, 799 mol) and Pd(OAc)2 (4.5 mg, 20.0 mol) were dissolved in NMP (1.6 mL ). The reaction mixture was stirred at 100 oC for 22 h and cooled to room temperature. The mixture was quenched with water (10 ml) treated with saturated aqueous NaHCO3 solution (3 ml), and extracted with EtOAc (3 ¡Á 30 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated by rotary evaporation. The residue was purified by column chromatography (1:1.5 hexane/EtOAc) to afford the compound 12k (33.4 mg, 22%) as a yellow solid. TLC: Rf 0.33 (1:1 hexane/EtOAc). mp: 112.5114.5 oC. 1H-NMR (400 MHz; CDCl3) delta 8.89 (d, 1H, J = 1.6 Hz), 8.88 (d, 1H, J = 1.6 Hz), 8.04 (d, 1H, J = 8.8 Hz), 8.01 (d, 1H, J = 1.6 Hz), 7.72 (t, 1H, J = 7.6 Hz), 7.62 (d, 1H, J = 7.6 Hz), 7.55 (dd, 1H, J = 8.8 Hz, J = 1.6 Hz), 7.26-7.14 (m, 5H), 7.11 (d, 1H, J = 7.6 Hz), 4.17 (s, 2H), 2.17 (s, 3H). 13C-NMR (100 MHz; CDCl3) delta 158.3, 149.2, 146.2, 145.9, 145.8, 142.8, 142.7, 139.2, 138.9, 133.4, 132.2, 130.7, 130.6, 129.2, 128.8, 128.7, 126.6, 123.6, 115.2, 31.4, 23.8. HRMS (ESI) calcd. for C23H19N6 (M+H): 379.1666; found 379.1662.

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

Reference£º
Article; Li, Fei; Park, Yunjeong; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry Letters; vol. 23; 4; (2013); p. 1083 – 1086;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1910-90-3,6-Bromoquinoxaline-2,3(1H,4H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 1 6-Bromo-2,3-dihydroxy-7-nitroquinoxaline To a solution of 0.5 g (2.1 mmol) of 6-bromo-2,3-dihydroxy quinoxaline in 5 ml of concentrated sulfuric acid is added at 0 C. 210 mg (2.1 mmol) KNO3. The solution is stirred at 0 C. for 30 min. and at 24 C. for 3 h. The reaction mixture is poured into ice-water giving 5 g precipitate. The crude product is dissolved in 30 ml of hot 2N NaOH. 4N HCl is added ajusting pH to 2 giving 0.4 g (67%) of 6-bromo-2,3-dihydroxy-7-nitro-quinoxaline, m.p. >300 C. NMR: two singlets (ppm 7.3 and 7.7 downfield from TMS).

1910-90-3, The synthetic route of 1910-90-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; A/S Ferrosan; US4812458; (1989); A;,
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91-19-0,91-19-0, Quinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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.

The synthetic route of 91-19-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ucar, Sefa; E?siz, Selcuk; Da?tan, Arif; Tetrahedron; vol. 73; 12; (2017); p. 1618 – 1632;,
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1233318-23-4, Methyl 2-(quinoxalin-6-yl)acetate is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Trimethylsilyldiazomethane [2.0M in hexanes] (0.08?xL) was added dropwise to a solution of quinoxalin-6-yl-acetic acid (0.030g, 0.159mmol) in toluene/methanol [8/1] (0.5mL) and stirred until the bubbling stopped. The reaction was then evaporated and the crude product was purified via silica gel column chromatography in hexane: ethyl acetate (1:1) to give 0.013g of quinoxaJin-6-yl-acetic acid methyl ester. This was added to a solution of hydrazine (O.lOinL) in methanol and stirred at room temperature overnight. The reaction mixture was evaporated in vacuo to give 0.019g of quinoxalin-6-yl-acetic acid hydrazide. 1H NMR (400 MHz, DMSO-d6) 8 9.77 (bs, IH), 9.35 (m, 2H), 8.46 (d, IH, J=8.8Hz), 8.39 (m, IH), 8.19 (dd, IH, J=2.0, 8.8Hz), 4.68 (bs, 2H), 4.07 (s, 2H)., 1233318-23-4

1233318-23-4 Methyl 2-(quinoxalin-6-yl)acetate 67428601, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/75567; (2007); A1;,
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1204-75-7, 3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The resulting compound (100 mg, 0.290 mmol) was condensed with 3-hydroxyquinoxaline-2-carboxylic acid (60.0 mg, 0.290 mmol) to afford N-[(1S)-1-{[4-(4-fluorophenoxy)piperidin-1-yl]carbonyl}-2-methylpropyl]-3-hydroxy-N-methylquinoxaline-2-carboxamide (88.0 mg, yield 63%) as a pale yellow solid. 1H-NMR (DMSO-d6, 400 MHz) delta: 12.74 (1H, brs), 7.81 (1H, d, J=7.8 Hz), 7.67 (1H, d, J=7.3 Hz), 7.61 (1H, d, J=11.2 Hz, 7.3 Hz), 7.38-7.32 (1H, m), 7.15 -7.10 (2H, m), 7.05-7.02 (2H, m), 5.08 (1H, d, J=11.5 Hz), 4.65-4.55 (1H, m), 4.12-4.06 (2H, m), 3.96-3.79 (2H, m), 2.77 and 2.76 (3H, s), 2.07-1.24 (5H, m), 0.97 (3H, dd, J=6.4 Hz, 2.4 Hz), 0.92 (3H, dd, J=6.4 Hz, 3.2 Hz). IR (ATR) cm-1, 3460, 2960, 1685, 1640, 1505, 1455, 1205, 1055. MS (ESI, m/z): 503 (M+Na)+. Anal. Calcd for C26H29FN4O4: C, 64.99; H, 6.08; F, 3.95; N, 11.66. Found: C, 64.69; H, 6.16; F, 4.14; N, 11.38.

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; Daiichi Sankyo Company, Limited; EP2258697; (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.6298-37-9,Quinoxalin-6-amine,as a common compound, the synthetic route is as follows.,6298-37-9

To a solution of 6-aminoquinoxaline (290 mg, 2 mmol) and hydroxypentadecanoic acid (518 mg, 2 mmol) in dichloromethane (40 ml) are added triethylamine (0.83 ml, 6 mmol), EDC (768 mg, 4 mmol) and HOBt (405 mg, 3 mmol). The mixture is stirred overnight at room temperature under inert atmosphere of nitrogen. The reaction is hydrolyzed, extracted with dichloromethane and then washed with a concentrated NH4Cl solution. The organic phase is dried on anhydrous MgSO4 and concentrated under reduced pressure. The residue obtained is then dissolved in DMF (10 ml), and then imidazole (136 mg, 2 mmol) and TBDMS-Cl (332 mg, 2.2 mmol) are added. The mixture is stirred overnight at room temperature under inert atmosphere of nitrogen. The reaction is hydrolyzed and then extracted with ethyl acetate, dried on anhydrous MgSO4 and concentrated under vacuum. The silylated product is purified on a silica column in a mixture of cyclohexane and ethyl acetate in a proportion of 8:2. The product is then dissolved in THF (10 ml) and TBAF (3 ml, 1 M in THF) is added. After 5 minutes the reaction is hydrolyzed and extracted with ethyl acetate. The organic phase is dried on anhydrous MgSO4 and concentrated under vacuum. The product is obtained with a total yield of 38% on three steps.

As the paragraph descriping shows that 6298-37-9 is playing an increasingly important role.

Reference£º
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE(CNRS); US2011/118270; (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.6309-61-1,6-Methylquinoxaline-2,3(1H,4H)-dione,as a common compound, the synthetic route is as follows.

6309-61-1, b. 1,4,6-trimethyl-1,4-dihydro-quinoxaline-2,3-dione. To a solution of 6-methyl-1,4-dihydro-quinoxaline-2,3-dione (5.3 g, 30 mmol) in THF (150 mL) was added, at 0 C. under argon, sodium hydride (3.68 g, 80% in mineral oil, 120 mmol) followed by methyl iodide (7.5 mL, 120 mmol). The solution was stirred at 0 C. for 3 hrs and at room temperature overnight. The reaction mixture was cooled to 0 C. and acidified with 1N HCl. The solution was extracted with dichloromethane washed with brine, dried (Mg2SO4), filtered and evaporated. The residue was chromatographed on silica gel (10 to 25% acetonitrile in dichloromethane) to give 1.1 g of 1,4,6-trimethyl-1,4-dihydro-quinoxaline-2,3-dione (18%). 1H NMR (300 MHz; CDCl3): 2.44 (s, 3 H), 3.66 (s, 6 H), 7.06-7.15 (m, 3 H).

6309-61-1 6-Methylquinoxaline-2,3(1H,4H)-dione 73225, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Pfahl, Magnus; Tachdjian, Catherine; Spruce, Lyle W.; Al-Shamma, Hussien A.; Boudjelal, Mohamed; Fanjul, Andrea N.; Wiemann, Torsten R.; Pleynet, David P.M.; US2003/144329; (2003); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.67074-63-9,4-Methyl-3,4-dihydroquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

A solution of 4-methyl-3,4-dihydroquinoxalin-2-(1H) -one (3.0 g, 18.5 mmol) in tetrahydrofuran (50 mL) Cooled to 0 C, lithium aluminum hydride (2.1 g, 55.3 mmol) was added in portions, The reaction was continued slowly to 25 C for 1 hour. The reaction solution was quenched with water (50 mL) ethyl acetate (30 mL x 3) was added, Combine organic phase, Dried over anhydrous sodium sulfate, filter, concentrate, The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1) To give the title compound (2.5 g, yield 91.3%)., 67074-63-9

As the paragraph descriping shows that 67074-63-9 is playing an increasingly important role.

Reference£º
Patent; Shandong Xuanzhu Pharmaceutical Co., Ltd.; Wu, Yongqian; (31 pag.)CN106317027; (2017); A;,
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