Category: 887590-25-2

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;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.

887590-25-2, 12.2: 4-{4-[4-(Pyridin-4-yloxy)piperidin-1-yl]phenyl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester 1.2 g of 4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine are placed in 20 ml of anhydrous o-xylene. 0.844 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is added, then 0.519 g of sodium tert-butoxide is added, followed by 0.032 g of palladium acetate, and then addition is completed with 0.029 g of tri(tert-butyl)phosphine. The reaction mixture is heated at 150 C. for 6 h. Heating is subsequently halted, the mixture is brought back to ambient temperature and ethyl acetate is added. The mixture is washed twice with water and then twice with a saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of a dichloromethane/methanol (99/1 to 97/3) mixture. 1.1 g of 4-{4-[4-(pyridin-4-yloxy)piperidin-1-yl]phenyl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester are obtained. M+H+=487

887590-25-2 tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate 16740533, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; SANOFI-AVENTIS; US2011/9391; (2011); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of tert-butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate obtained in Reference Example 28 (1.06 g) in tetrahydrofuran (20 ml), sodium hydride (60% suspension in oil, 181 mg) was added and stirred for 5 minutes, followed by addition of methyl iodide (281 mul). After stirring at room temperature for 1 hour, sodium hydride (60% suspension in oil, 181 mg) was further added and stirred for 30 minutes, followed by addition of methyl iodide (281 mul). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate = 10:1 to 5:1) to give tert-butyl 4-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (331 mg) as a brown powder. To a solution of tert-butyl 4-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate thus obtained (331 mg) in ethyl acetate (2 ml), 4N hydrochloric acid (in ethyl acetate, 1.1 ml) was added and stirred overnight at room temperature. The reaction mixture was diluted with 8M aqueous sodium hydroxide and then extracted with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure to give the titled compound, i.e., 1-methyl-1,2,3,4-tetrahydroquinoxaline (179 mg) as a brown oil. 1H NMR (300 MHz, CHLOROFORM-D) delta 2.86 (s, 3 H), 3.23-3.31 (m, 2 H), 3.44-3.52 (m, 2 H), 3.68 (brs, 1 H), 6.43-6.51 (m, 1 H), 6.53-6.62 (m, 2 H), 6.63-6.72 (m, 1 H)., 887590-25-2

The synthetic route of 887590-25-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Taisho Pharmaceutical Co. Ltd.; EP2172453; (2010); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.

887590-25-2, A partial solution of tert-butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate (100 mg, 0.467 mmol), 1,3-dibromobenzene (220 mg, 0.933 mmol), C52CO3 (608 mg, 1.867 mmol) in toluene (1 mL), was purged and degassed with N2, then 2,2?- bis(diphenylphosphino)-1,1?-binaphthalene (58.1 mg, 0.093 mmol) and palladium(II) acetate (20.95 mg, 0.093 mmol) were added, and the vessel was purged and degassedagain. The reaction flask was capped and stirred at 110 C overnight. The mixture was cooled, water (15 mL) was added and extracted with ethyl acetate (15 mL x 3). The combined organic layers were washed with brine, dried over Na2504, and concentrated. The residue was purified on silica gel with a gradient of 0-100% EtOAc in hexanes to give tert-butyl 4-(3 -bromophenyl)-3 ,4-dihydroquinoxaline- 1 (2H)-carboxylate (120 mg66.1% yield) as a white solid. LCMS M = 389.10/391.15. Method G. Retention time4.175 mm.

The synthetic route of 887590-25-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

887590-25-2,887590-25-2, 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

To a solution of tert-butyl 3,4-dihydro-2H-quinoxaline-1-carboxylate (17 g, 72.6 mmol) in MeCN (150 mL) was added N-bromosuccinimide (12.3 g, 68.9 minol) by portionwise at 0 C. The mixture was stirred at 0 C for I h. The reaction was quenched with water (200 mE), extracted with EtOAc (200 mE x 3). The combined organic layers were dried over anhydrousNa2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc 20: 1 to 4: 1) to give the title compound (14.0 g, 62%) as a light yellow solid. ?H NMR (400 MHz, DMSO-d6) 8 7.50 (s, iH), 6.95 – 6.92 (m, 1H), 6.52 – 6.50 (m, IH), 6.29 (s, 1H), 3.58 – 3.56 (m, 2H), 3.24 – 3.23 (m, 2H), 1.45 (s, 9H).

887590-25-2 tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate 16740533, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.

3.2: 4-[4-(4-(Benzyloxycarbonyl)piperazin-1-yl)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester 8.43 g of 4-(4-bromophenyl)piperazine-1-carboxylic acid benzyl ester are placed in a 500 ml three-necked flask under a nitrogen atmosphere. 170 ml of anhydrous o-xylene, 5.01 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester and then 3.08 g of sodium tert-butoxide are added, followed by 0.48 g of palladium acetate, and then the addition is completed with 0.53 ml of tri(tert-butyl)phosphine. The reaction mixture is heated at 150 C. for 18 h. Heating is halted and the mixture is brought back to ambient temperature. The o-xylene is evaporated and the mixture is taken up in ethyl acetate before filtering it through celite. The organic phase is washed with water and then with a saturated aqueous sodium chloride solution. The aqueous phase is extracted with ethyl acetate. The organic phases are combined and then dried over sodium sulphate, filtered through a sintered glass filter and concentrated under vacuum. 8.9 g of 4-[4-(4-(Benzyloxycarbonyl)piperazin-1-yl)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester are obtained after purification on a silica column, elution being carried out with a gradient of heptane/ethyl acetate solvent varying from 95/5 to 60/40). M+H+=529, 887590-25-2

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

Reference£º
Patent; SANOFI-AVENTIS; US2011/9391; (2011); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.

887590-25-2, To a round bottom flask charged with compound 14-2 (90mg, 0.38 mmol) and methyl 4-(bromomethyl)benzoate (87 mg, 0.38 mmol) in DMF (5 mL) was added K2CO3 (105 mg, 0.76 mmol). The resulting mixture was allowed to stir for 2 h at 80 C. The mixture was cooled to room temperature and after addition of water (15 mL) extracted with EtOAc (3 x 15 mL). The combined organic extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by flash chromatography (0 – 5% MeOH/DCM), and the title compound was obtained as an off- white waxy solid (90 mg, 60%).1H NMR (CDCI3) delta 7.99, 7.32 (AlphaAlpha’ChiChi’ multiplet, AX + /AX’ = 8.2 Hz, 4H), 7.48 (br d, / = 7.4 Hz, 1H), 7.32 (d, / = 7.9 Hz, 2H), 6.90 (incompletely resolved ddd approaching dt, average of two larger / = 7.8 Hz, additional / = 1.1 Hz, 1H), 6.66 (incompletely resolved ddd approaching dt, average of two larger / = 7.6 Hz, additional / = 1.2 Hz, 1H), 6.55 (dd, / = 8.2 Hz, 0.9 Hz, 1H), 4.56 (s, 2H), 3.90 (s, 3H), 3.86, 3.44 (AA’XX’ multiplet, AX + /AX’ = 10.2 Hz, 4H), 1.53 (s, 9H). 13C NMR (DMSO- 6) delta 166.9, 153.3, 143.7, 138.2, 130.1 (2C), 129.1, 126.5 (2C), 125.1, 124.7, 116.3, 111.6, 100.0, 81.1, 54.9, 52.1, 49.5, 41.6, 28.4 (3C). ESI LRMS: [M+H]+, mlz 383.3.

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

Reference£º
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; KOZIKOWSKI, Alan; SHEN, Sida; BERGMAN, Joel; (100 pag.)WO2017/142883; (2017); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.

EXAMPLE 1 4-[4-(Pyrimidin-2-ylmethoxy)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid adamantan-2-ylamide (Compound No. 3) 1.1: tert-Butyl ester of 4-(4-hydroxyphenyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 0.3 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester, 0.183 g of 4-bromophenol, 0.0079 g of 2′-(dimethylamino)-2-biphenylyl-palladium(II) chloride dinorbornylphosphine complex and 0.363 g of potassium triphosphate in 3.4 ml of ethylene glycol dimethyl ether are placed under an inert atmosphere. 4.16 ml of lithium bis(trimethylsilyl)amide and 2.17 ml of ethylene glycol dimethyl ether are added. The reaction mixture is stirred at 80 C. for 4 h. After cooling, the reaction medium is taken up in dichloromethane. A 1N aqueous hydrochloric acid solution is added to pH 1, the pH is then brought back to 8 with a saturated aqueous sodium hydrogencarbonate solution and the mixture is extracted with dichloromethane. The organic phases are combined, washed with water and with a saturated aqueous sodium chloride solution, and dried over magnesium sulphate. After concentrating to dryness, the crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of methanol in dichloromethane varying from 0% to 2.5%. 0.34 g of the tert-butyl ester of 4-(4-hydroxyphenyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid is obtained. M+H+=327, 887590-25-2

The synthetic route of 887590-25-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SANOFI-AVENTIS; US2011/9391; (2011); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

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

Example 13; N-(Piperidin-1-yl)-4-{4-[3-(1H-pyrazol-4-yl)pyrrolidine-1-carbonyl]-3,4-dihydro-2H-quinoxalin-1-yl}benzamide (Example 172); 13.1: tert-Butyl 4-(4-cyanophenyl)-3,4-dihydroquinoxaline-1(2H)-carboxylate; 1 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester, 10 ml of N-methylpyrrolidinone, 0.57 g of 4-fluorobenzonitrile and 0.96 g of potassium tert-butoxide are introduced into a 20 ml glass tube. The reaction medium is stirred for 5 min, water is added and extraction is carried out 3 times with diethyl ether. The organic phases are combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel eluted with a gradient of ethyl acetate from 3.5% to 35% in heptane. 0.9 g of tert-butyl 4-(4-cyanophenyl)-3,4-dihydroquinoxaline-1(2H)-carboxylate is obtained.M+H+=336

The synthetic route of 887590-25-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SANOFI-AVENTIS; US2009/176775; (2009); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

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

Example 6; 1-Butyl-4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoxaline Hydrochloride (Compound No. 119); 6.1: tert-Butyl 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydroquinoxaline-1(2H)-carboxylate; 2.75 g of the tert-butyl ester of 3,4-dihydro-1(2H)-quinoxalinecarbamic acid, 117 ml of dichloromethane and 5.8 ml of diisopropylethylamine are placed in a 500 ml round-bottomed flask under a nitrogen atmosphere. 1.74 g of triphosgene are added at 0 C. and then the reaction mixture is left stirring at ambient temperature for three hours. 2 ml of diisopropylethylamine and 1.83 g of 3-(pyrrolidin-3-yl)pyridine are subsequently added and the reaction mixture is stirred for eighteen hours. 200 ml of a saturated aqueous sodium hydrogencarbonate solution are added and then the aqueous phase is extracted three times with dichloromethane. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture. 3.72 g of tert-butyl 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydroquinoxaline-1(2H)-carboxylate are obtained.M+H+=409.3, 887590-25-2

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

Reference£º
Patent; SANOFI-AVENTIS; US2009/176775; (2009); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider