Category: Triazoles

Electric Literature of 13273-53-5,Some common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, 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.

A mixture of 2-((4-chlorophenethyl)amino)-2-phenyl-l-(6-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-lH-indol-3-yl)ethan-l-one (0.06 g, 0.11 mmol), 4-bromo-l -methyl – 1H- 1,2, 3 -triazole (0.019 g, 0.11 mmol), and cesium carbonate (0.095 g, 0.29 mmol) in a mixture of 4:1 dioxane:water (5 ml) was degassed for 20 minutes with argon. S-Phos Pd precatalyst G3 (0.009 g, 0.01 mmol) was added and degassing was continued for another 10 minutes. The reaction mixture was heated in a sealed tube with microwave heating at 135 C for 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was treated with water (15 ml) and extracted with ethyl acetate (2 x 15 ml). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the title compound as solid (0.040 g, 74%) in racemic form.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methyl-1H-1,2,3-triazole, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMCEUTICALS, INC.; WILSON, Jonathan, E.; LEVELL, Julian, R.; (152 pag.)WO2019/161157; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7170-01-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3 -methyl- IH-1, 2,4-triazole (2.20 g, 26.4 mmol), l,5-difluoro-2- methoxy-4-nitrobenzene (5.00 g, 26.4 mmol), and potassium carbonate (3.65 g, 26.4 mmol) in anhydrous DMSO (50 mL) was heated at 80 0C for 24 h. The reaction mixture was allowed to cool to rt and was poured into 500 mL of water/10 mL brine solution. The aqueous mixture was extracted with EtOAc (2 x 250 mL). The combined organic extracts were washed with water (500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel column chromatography (50% EtOAc/hexane) to afford l-(5-fluoro-2-methoxy-4-nitrophenyl)-3- methyl-lH-l,2,4-triazole (1.24 g, 18 % yield). LC-MS (M+H)+ = 253.2. 1H NMR (SOO MHz, CDCl3) delta ppm 8.95 (s, 1 H) 8.00 (d, J=I 1.60 Hz, 1 H) 7.80 (d, J=6.10 Hz, 1 H) 4.09 (s, 3 H) 2.50 (s, 3 H).

The synthetic route of 3-Methyl-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, III, Lorin A.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2011/14535; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1001401-62-2, 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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of A-I (0.72 g, 3.8 mmol) and thionyl chloride (0.36 mL, 5.0 mmol) in toluene (7.0 mL) and a drop of DMF is heated to 60C for 2h, then cooled and concentrated. The residue isdissolved in dry DCM (5 mL) and added dropwise to a stirred mixture of B-I (0.65 g, 4.64 mmol)and TEA (1.44 mL, 10.3 mmol) in dry DCM (10 mL) at 0C. The reaction is stirred at RTfor2h.Water is added and the organic layer is separated, washed with citric acid (10% aq. solution)and with NaHCO3 (sat. aq. solution). The organic layer is dried and concentrated to provide 0.94g of C-4. ESI-MS: 275 [M+H], HPLC (Rt): 0.69 mm (method M)

The chemical industry reduces the impact on the environment during synthesis 2-(2H-1,2,3-Triazol-2-yl)benzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; (65 pag.)WO2017/178339; (2017); 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. 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 5-Amino-4H-1,2,4-triazole-3-carboxylic acid

General procedure: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

The synthetic route of 3641-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-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. Recommanded Product: 1-Methyl-1H-1,2,3-triazole

A solution of 1-methyl-1H-1, 2, 3-triazole (3.0 g, 36.1 mmol) in anhydrous THF (100 mL) was cooled to -78 , followed by the addition of butyllithium (15.89 mL, 39.7 mmol) dropwise to give a yellow suspension. The reaction mixture was stirred at -78 for 1 h before N-methoxy-N-methylacetamide (6.52 g, 63.2 mmol) was added. The white suspension was then allowed to warm to 10 and stirred for 16 h. The reaction was quenched with MeOH. This solution was purified by column chromatography on silica gel (petroleum ether /EtOAc 3: 1to 1: 1) to give the product as a solid.1H-NMR: (Chloroform-d400MHz) delta 8.16 (s, 1H) , 4.31 (s, 3H) , 2.58 (s, 3H)

The synthetic route of 1-Methyl-1H-1,2,3-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ARASAPPAN, Ashok; BUNGARD, Christopher James; FRIE, Jessica L.; HAN, Yongxin; HOYT, Scott B.; MANLEY, Peter J.; MEISSNER, Robert S.; PERKINS, James; SEBHAT, Iyassu K.; WILKENING, Robert R.; (140 pag.)WO2016/29454; (2016); 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. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H7N3O2

General procedure: General procedure: A mixture of 4-phenylurazole (1, 1 mmol), aryl aldehyde (2, 1.1 mmol) or ketone (5, 1.1 mmol), 1,3-diketone (3, 1 mmol) and FeCl3 (16.2 mg, 10 mol%) in acetonitrile (2.5 mL) was stirred in preheated oil bath at reflux for a specified time as required to complete the reaction (see Table 2 and 3). After complete conversion, as indicated by TLC, the solvent was removed in vacuo and the residue was diluted with water and extracted with ethyl acetate (2¡Á10 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (Merck, 60-120 mesh, ethyl acetate:hexane, 4:6) to afford the pure triazolo[1,2-a]indazoletrione or spirotriazolo[1,2-a]indazoletetraonederivative.

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 15988-11-1.

Reference:
Article; Subba Reddy; Umadevi; Narasimhulu; Yadav; Chemistry Letters; vol. 42; 8; (2013); p. 927 – 929;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7411-23-6, These common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-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.

Weigh the raw material 3,5-dibromo-1,2,4-triazole in 50mL of dichloromethane solution.After slowly adding the tungyl acid chloride at a molar ratio of 1: 2, the reaction was started under reflux at 0 C for 2 hours.Follow-up detection by thin-layer chromatography. After the reaction is completed, an appropriate amount of water is added and washed 3 times.Dichloromethane was added and shaken for extraction. The lower layer of the liquid was removed under reduced pressure to remove the solvent, and dried over anhydrous sodium sulfate.The obtained crude product was added with absolute ethanol at a ratio of 1: 1 g / mL, and recrystallized at -20 C.After filtration, the solvent was evaporated to obtain the corresponding compound 2,

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

Reference:
Patent; China Institute Of Forestry Forest Products Chemical Industry Institute; Huang Lixin; Cheng Jiang; Zhang Caihong; (6 pag.)CN110835322; (2020); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 41253-21-8, 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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 C. for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) ?: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 C. for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) ?: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

The chemical industry reduces the impact on the environment during synthesis Sodium 1,2,4-triazol-1-ide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); 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. 288-88-0, name is 1H-1,2,4-Triazole, A new synthetic method of this compound is introduced below., Formula: C2H3N3

Intermediate 82: step a 4-(1H-1,2,4-triazol-1-yl)benzaldehyde 4- Fluorobenzaldehyde (12.0 mL, 1 12 mmol) was added dropwise by syringe to a stirring, heterogeneous mixture of 1,2,4-triazole (11.6 g, 168 mmol) and potassium carbonate (24.7 g, 179 mmol) in dimethyl formamide (220 mL) at 23 C. The mixture was heated to 105 C. After 3.5 hours, the mixture was allowed to cool to 23 C. The cooled solution was transferred to a 2 L Erlenmeyer flask and diluted with water (500 mL) and ethyl acetate ( 200 mL). The biphasic mixture was stirred until the layers cleanly separated. The layers were separated. The organic layer was washed with half-saturated aqueous sodium chloride solution (3 100 mL). The washed solution was dried with sodium sulfate, and the dried solution was filtered. The filtrate was concentrated to provide an off-white solid. The solid was suspended in a mixture of heptanes and isopropyl acetate (5: 1, 600 mL). The mixture was filtered and the filter cake was washed with heptanes-isopropyl acetate (5: 1). The solids were collected and dried under vacuum to afford the title compound as a white solid.

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; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); 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 16681-70-2 as follows. Application In Synthesis of 1H-[1,2,3]Triazole-4-carboxylic acid

A solution of Compound 1 (18.1 mg, 37 mumol) in HCl (185 muL, 740 mumol) was stirred at room temperature for 30 minutes. After this time, LCMS indicated that the boc group had been cleaved so the solution was concentrated in vacuo. A solution of 3H-[1,2,3]triazole-4-carboxylic acid (5.0 mg, 44 mumol) and HATU (17 mg, 44 mumol) in DMF (370 muL) was stirred at room temperature for 30 minutes. After this time, a solution of the crude amine in DMF (370 muL) was added, followed by DIPEA (19 muL, 111 mumol). The resulting mixture was stirred at room temperature for 1 hour, and then concentrated in vacuo. The crude residue was purified by preparative HPLC to yield 3 products with identical masses (2 of which are diastereomers): isomer a (3.5 mg; purity 97%), isomer b (1.2 mg; purity 100%), and isomer c (1.1 mg; purity 100%). MS m/z [M+H]+ calc’d for C24H23ClFN5O33, 484.15. found 484.2.

According to the analysis of related databases, 16681-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics