Tag: M.W:200-300

Synthetic Route of 23579-79-5, These common heterocyclic compound, 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

LiHMDS (1 Min THF, 420 mL, 420 mmol) was added dropwise at 0 C to a cooled (ice bath) solution of 3-amino-4-fluorobenzotrifluoride (70 mL, 527.8 mmol) and 1H-1,2,4-Triazole, 3,5-dibromo-1-methyl-(46a, 50 g, 207.6 mmol) in anhydrous THF (500 mL). The reaction mixture was stirred at room temperature (rt) for 20 h. A saturated aqueous NH4Cl solution was added slowly. The reaction mixture was extracted with dichloromethane (DCM) and the organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The resulting slurry was triturated in heptane/DIPE and a solid was formed,filtered and dried under vacuum at 60 C, to provide 65 in 78% yield; mp 159.2 C. 1H NMR (600 MHz, CDCl3) delta ppm 3.77 (s, 3H), 6.37 (d, J = 3.9 Hz, 1H),7.20-7.24 (m, 1H), 7.27-7.29 (m, 1H), 8.34 (dd, J = 7.7, 2.2 Hz, 1H). MS (ESI) m/z 339 [M+H].+ Anal. (C10H7BrF4N4) C, H, N.

Statistics shows that 3,5-Dibromo-1-methyl-1H-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 23579-79-5.

Reference:
Article; Velter, Adriana I.; Bischoff, Franois P.; Berthelot, Didier; De Cleyn, Michel; Oehlrich, Daniel; Jaroskova, Libuse; Macdonald, Gregor; Minne, Garrett; Pieters, Serge; Rombouts, Frederik; Van Brandt, Sven; Van Roosbroeck, Yves; Surkyn, Michel; Trabanco, Andrs A.; Tresadern, Gary; Wu, Tongfei; Borghys, Herman; Mercken, Marc; Masungi, Chantal; Gijsen, Harrie; Bioorganic and Medicinal Chemistry Letters; vol. 24; 24; (2014); p. 5805 – 5813;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7411-23-6, A common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 3,5-dibromo-lh-l,2,4-triazole (150.0 g, 661.2 mmol) in tetrahydrofuran (1500 mL) was slowly added p-toluenesulfonic acid (17.1 g, 99.2 mmol), followed by 3,4-dihydro-2h-pyran (166.9 g, 1983.6 mmol) at 0 C. After addition, the reaction mixture was heated at 70 C for 3 h and concentrated under reduced pressure. The residue was poured into water (500 mL) and adjusted to pH = 9 by addition of saturated aqueous sodium bicarbonate. The resulting mixture was extracted with ethyl acetate (3 x 400 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduce pressure. The resulting crude product was washed with methanol (2 x 50 mL), dried under reduced pressure to give crude 3,5-dibromo-l-tetrahydropyran-2-yl-l,2,4- triazole (155 g, 75%) as a white solid. XH NM (400 MHz, CDCI3) delta 5.49 – 5.46 (m, 1H), 4.12 – 3.99 (m, 1H), 3.72 – 3.61 (m, 1H), 2.38 – 2.26 (m, 1H), 2.18 – 2.07 (m, 1H), 1.98 – 1.90 (m, 1H), 1.78 – 1.60 (m, 3H).

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; HAMILTON, Gregory; PATEL, Snahel; ZHAO, Guiling; DANIELS, Blake; STIVALA, Craig; (208 pag.)WO2019/72942; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, A new synthetic method of this compound is introduced below., Quality Control of 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Ethanol 620g was first added to a 1L four-necked flask at room temperature.Compound IV (106.9 g, 0.4 mol) was added with stirring and compound Vc (57 g, 0.22 mol) was added.Slowly warming to 50-55C under nitrogen protection, completely dissolved solids,Potassium bicarbonate 48 g was added in portions over 60-80 minutes. After the addition, the reaction is incubated at 50-55C for 2-3 hours.The disappearance of the raw material point monitored by TLC represents the end of the reaction.After the reaction was completed, insoluble material was removed by hot filtration, and the resulting filtrate was slowly cooled to -5C.A large number of white solids precipitated, and 100 ml of deionized water was added dropwise to the reaction flask over 1-2 hours to crystallize sufficiently.And remove inorganic salts. After deionized water is added, it is crystallized at -5C for 2 hours.Filter and filter cake washed with 100 ml of 95% ice-cold ethanol.The resulting compound (IIIb) was dried under vacuum and dried at a temperature of 50-55C for 24 hours.124 g of compound (IIIb) was obtained in a yield of 86%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Zhejiang Xin Donggang Pharmaceutical Co., Ltd.; Yan Jianbo; Ma Liangxiu; Lin Yi; Hong Huabin; (16 pag.)CN107739344; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7411-23-6, A common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Sodium tert-butoxide (372 mg, 3.9mmol) was added to a solution of 3,5-dibromo-1H-1,2,4-triazole (800 mg, 3.53 mmol) in DMF (5 mL), and stirred at RT for 15 min. 1-bromo-2-methylpropane (531 mg, 3.9 mmol) was added dropwise and the reaction heated to 50 C for 2 h and then RT for 18 h. The reaction was quenched with water (50 mL) and extracted with diethyl ether (3 ¡Á 10 mL). The combined organics were washed with brine and dried over sodium sulfate. The solvent was removed in vacuo to yield 3,5-dibromo-1-isobutyl-1,2,4-triazole (276 mg, 0.97 mmol, 27% yield) as a colourless oil.1H NMR (400 MHz, CDCl3) delta 3.94 (dd, J = 7.3, 1.0 Hz, 2H), 2.34- 2.22 (m, 1H), 0.96 (dd, J = 6.8, 0.9 Hz, 6H).

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 23579-79-5 as follows. Recommanded Product: 23579-79-5

Bis(triphenylphosphine)palladium(II) chloride (0.087 g, 0.12 mmol) was added to a stirred mixture of tert-butyl N-tert-butoxycarbonyl-N-[3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-trimethylstannyl-2-pyridyl]carbamate 5a (3 g, 4.13 mmol), 3,5-dibromo-1-methyl-1,2,4-triazole 27 (1 g, 4.15 mmol) and lithium chloride (0.528 g, 12.4 mmol) dissolved in DME (8 mL) under argon. The resulting mixture was heated at 140 C for 30 min in a microwave apparatus. More bis(triphenylphosphine)palladium(II) chloride (0.087 g, 0.12 mmol) was added and the mixture was heated at 130 C for 30 min in the microwave. The mixture was evaporated under reduced pressure, adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 5 to 50% ethyl acetate in dichloromethane to afford tert-butyl N-[5-(5-bromo-2-methyl-1,2,4-triazol-3-yl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (1.4 g, 58%) as a solid. Bis(triphenylphosphine)palladium(II) chloride (170 mg, 0.24 mmol) was added to a stirred mixture of tert-butyl N-[5-(5-bromo-2-methyl-1,2,4-triazol-3-yl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (1.40 g, 2.42 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate 28 (748 mg, 2.42 mmol) and cesium fluoride (1.10 g, 7.26 mmol) in methanol (4 mL) under argon atmosphere. The resulting mixture was heated at 140 C for 40 min in a microwave apparatus. More bis(triphenylphosphine)palladium(II) chloride (1.02 g, 1.45 mmol) was added and the mixture was degassed and heated at 140 C for 30 min in the microwave. After cooling, the mixture was adsorbed on silica gel with methanol / ammonia and was purified by flash chromatography on silica gel eluting with 1 to 4% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford tert-butyl 4-(5-(6-(tert-butoxycarbonylamino)-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-1-methyl-1,2,4-triazol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (956 mg, 68%) as a yellow solid. A slurry of palladium (175 mg, 1.65 mmol) and tert-butyl 4-(5-(6-(tert-butoxycarbonylamino)-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-1-methyl-1,2,4-triazol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (956 mg, 1.65 mmol) and ammonium formate (1.04 g, 16.5 mmol) dissolved in DMF (30 mL) was heated at 70 C for 2 h. More palladium (175 mg, 1.65 mmol) was added. The mixture was heated one more hour. The resulting slurry was filtered and the filtrate was concentrated to dryness. Water (50 mL) was added. The mixture was stirred for 1 h, filtered and dried under reduced pressure to afford crude tert-butyl 4-(5-(6-(tert-butoxycarbonylamino)-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-1-methyl-1,2,4-triazol-3-yl)piperidine-1-carboxylate (562 mg, 59%) as a yellow solid. Trifluoroacetic acid (1.5 mL) was added to a stirred suspension of tert-butyl 4-(5-(6-(tert-butoxycarbonylamino)-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-1-methyl-1,2,4-triazol-3-yl)piperidine-1-carboxylate (562 mg, 0.96 mmol) in dichloromethane (2 mL). The resulting solution was stirred at 25 C for 1 h. The solvents were evaporated. Traces of TFA were removed by azeotroping with toluene. The crude product was dissolved in methanolic solution of ammonia, adsorbed on silica gel, and purified by flash chromatography on silica gel eluting with 2 to 8% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1,2,4-triazol-5-yl)pyridin-2-amine (332 mg, 90%) as a beige solid. Acetyl chloride (0.022 mL, 0.31 mmol) was added over a period of 15 min to a stirred solution of 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1,2,4-triazol-5-yl)pyridin-2-amine (100 mg, 0.26 mmol) and triethylamine (0.073 mL, 0.52 mmol) dissolved in dichloromethane (3 mL) at 0 C. The resulting solution was stirred at 0C for 1 hour. The mixture was adsorbed on silica gel with a 7 N methanolic solution of ammonia. The crude product was purified by flash chromatography on silica gel eluting with 2 to 4% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 1-[4-[5-[6-amino-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]-1-methyl-1,2,4-triazol-3-yl]-1-piperidyl]ethanone 5 (80 mg, 72%) as a yellow foam.

According to the analysis of related databases, 23579-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Barlaam, Bernard; Cosulich, Sabina; Delouvrie, Benedicte; Ellston, Rebecca; Fitzek, Martina; Germain, Herve; Green, Stephen; Hancox, Urs; Harris, Craig S.; Hudson, Kevin; Lambert-Van Der Brempt, Christine; Lebraud, Honorine; Magnien, Francoise; Lamorlette, Maryannick; Le Griffon, Antoine; Morgentin, Remy; Ouvry, Gilles; Page, Ken; Pasquet, Georges; Polanska, Urszula; Ruston, Linette; Saleh, Twana; Vautier, Michel; Ward, Lara; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5155 – 5162;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 956317-36-5,Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

5-chloro-2-[(5R)-hexahydro-5-methyl-i H-i ,4-di-azepin-i -yl]benzoxazole (75 mmol) was dissolved in N,NDimethylformamide (75 ml), then cooled to 0 to 5 C., and added with 5-methyl-2-(2H- 1 ,2,3-triazole-2-yl)benzoic acid (79 mmol), HOAt (82.8 mmol), EDCI (82.8 mmol) and triethylamine (188 mmol); then the mixture was warmed naturally and stirred at room temperature overnight. 10 mass % citric acid solution was added, and the aqueous phase separated was extracted with ethyl acetate. The resulted organic phase was washed with 5% sodium carbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtrated and dried by evaporation, to give suvorexant with a yield of 97%, and the cc value is 99.8%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, its application will become more common.

Reference:
Patent; Zhejiang Huahai Pharmaceutical Co., Ltd.; Shanghai Aobo Pharmtech, Inc., Ltd.; Lin, Jianping; Guo, Xiaowen; Gao, Xiaofei; Huang, Chao; Guo, Yuanbing; Tao, Anping; Huang, Luning; Gu, Hong; (15 pag.)US2019/40052; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C2HBr2N3

In a 100 mL round-bottomed flask, 3,5-dibromo-lH-l ,2,4-triazole (5g, 22.0 mmol, Eq: 1.00), l-(chloromethyl)-4-methoxybenzene (3.45 g, 22.0 mmol, Eq: 1) and N-ethyl-N- isopropylpropan-2-amine (5.7 g, 44.1 mmol, Eq: 2) were combined with acetonitrile (101 ml) to give a light yellow solution. Potassium iodide (1.83 g, 11.0 mmol, Eq: 0.5) was added. The mixture was heated to reflux for 2 hours. The reaction mixture was cooled and diluted with EtOAc (100 mL), washed with H20 (50 mL) and brine (50 mL). The organic layer was dried over anhydrous MgS04, filtered and volatiles were removed under reduced pressure to yield an oil from which the compound was isolated by column chromatography (Hexanes/EtOAc = 70/30) to product 7.3 g (95%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7411-23-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole, belongs to Triazoles compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 22300-52-3, Quality Control of 4,5-Dibromo-2H-1,2,3-triazole

3- Fluoro-4-nitrotoluene (1367 g, 1 eq.), 4,5-dibromo-2/-/-1 ,2,3-triazole (1999 g, 1 eq.), K2C03 (1340 g, 1.1 eq.) and DMF (1 1 L) is heated to 75 C for 15 h. The reaction mixture is cooled to 22 C and treated with water (18 L). The resulting suspension is filtered, washed with water (4 L). The product is washed with isopropanol (5 L), and dried under reduced pressure to yield a white solid. Yield: 281 1 g, 88%. Purity: 100% a/a (LC-MS method 2). 1H NMR (400 MHz, DMSO) <5: 8.10 (d, J = 8.3 Hz, 1 H), 7.86 (d, J = 1.0 Hz, 1 H), 7.66 (dd, J1 = 0.9 Hz, J2 = 8.3 Hz, 1 H), 2.51 (s, 3 H). If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it. Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; DOeRRWAeCHTER, Patric; SCHMIDT, Gunther; (48 pag.)WO2018/202689; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, A new synthetic method of this compound is introduced below., Safety of 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Add intermediate I48kg (235mol) in the reaction vessel, add dichloromethane 300ml, start stirring, add Intermediate II48kg (235mol); add alkali stirring and mixing, add condensing agent EDC.HCL45kg, when added, control the temperature at 25 The following, the reaction was incubated at 24 ~ 27 , TLC monitoring, TLC showed the reaction was completed, the intermediate was obtained after 87kg (223mol), the yield 94.9%.The difference between Example 3 and Example 1 is that a combination of a condensing agent and a condensing agent such as 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and tris (2 , 6-dimethoxyphenyl) bismuth, the weight percentage of tris (2,6-dimethoxyphenyl) bismuth in the condensing agent is 25%Insulation 18 ~ 22 reaction, TLC monitoring, post-processing intermediate 88kg (225.6mol),Yield 96%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Anhui Baishansheng Pharmaceutical Co., Ltd.; Chang Song; Wang Zheming; Wei Yong; Mu Longzhi; Wu Zhangshuan; Fan Zheng; (8 pag.)CN107298678; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 956317-36-5, A common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In the 50 L reaction flask A,10 kg of 5-methyl-2- (1,2,3-triazol-2-yl) benzoic acid,1.5 L dichloromethane,Ice bath to 0 ,Under nitrogen, 640 g of oxalyl chloride was added,100 g of DMF,The reaction was stirred at room temperature for 2 h.In another 100L reaction flask B,1.25 kg of compound 6 was added,1 kg of triethylamine,30 L of dichloromethane,Stir at room temperature for 2h and then cool the ice bath to 0 C,Dropping the mixture in the reaction flask A,Drop finished,Placed at 10 C,HPLC monitoring. After the reaction,The reaction solution was diluted with water,And then extracted with DCM,The DCM phase was dried over anhydrous sodium sulfate,And finally concentrated under reduced pressure at 45 C to obtain a crude product,The crude product was passed through a column of silica gel (60-120 mesh)The eluent was a 2% methanol / dichloromethane system,The compound 7 was concentrated in a brown oily liquid,Weight 1.98 kg, yield: 88%.

The synthetic route of 956317-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Meiyugao Pharmaceutical Co., Ltd.; Chen Zhiyong; Wang Chunyan; Wang Cong; (26 pag.)CN106866632; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics