Triazoles

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. 151899-62-6, name is 3-Iodo-1-trityl-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., Quality Control of 3-Iodo-1-trityl-1H-1,2,4-triazole

Nitrogen gas was bubbled through a solution of 3-iodo-l-trityl-lH-l,2,4-triazole (37.3g, 85.35mmol), and triethylamine (17.8ml, 128mmol) in anhydrous DMF (300ml) heated at 350C for 30 mins. Pd(PPh3)2Cl2 (2Ag, 3.4mmol) and CuI (651mg, 3.4mmol) were added followed by addition of ethynyltrimethylsilane (18ml, 128mmol) in anhydrous DMF (18ml) over 5 15 hours via syringe pump. After complete addition the mixture was heated at 350C for a further 5 hours. The mixture was poured into water (700ml) and extracted with EtOAc (3 x 300ml). Combined EtOAc layers washed with water (2 x 500ml), sat. NaCl (250ml), dried over Na2SO4, filtered and evaporated. The residue was purified by MPLC on silica gel eluting with a gradient from 100% hexanes to 10% EtOAc in hexanes to afford the title compound. 1HNMR (500 MHz, 10 CDCl3) delta: 7.96 (s, IH), 7.37 (m, 9H), 7.14 (m, 6H), 0.27 (s, 9H).

The synthetic route of 151899-62-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/57336; (2008); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 584-13-4, name is 4H-1,2,4-Triazol-4-amine, 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 584-13-4, Quality Control of 4H-1,2,4-Triazol-4-amine

General procedure: 4-Carboxybenzenesulphonamide (10.0mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 12.0mmol), and 1-hydroxybenzotriazole (HOBt, 12.0mmol) were added to 10mLN,N-dimethylformamide (DMF) and stirred at room temperature (20-25C) for 30min. Then, 2-amino-4-ethoxycarbonyl thiazole (12.0mmol) and 4-dimethylaminopyridine (DMAP, 3.0mmol) were added to the solution. The reaction was carried out at 45C for 24h. The mixture was cooled to room temperature and extracted with ethyl acetate (EtOAc). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (dichloromethane/methanol, 60:1-30:1) to recover compound 2a. The method for synthesising 2b-3f was the same as for 2a.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4H-1,2,4-Triazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cheng, Yunyun; Feng, Yan; He, Xinhua; Li, Zhenwang; Sun, Xianyu; Wang, Jing; Yang, Chaofu; Yang, Xu; Zhang, Jiwen; Zhao, Wangyu; Zhuang, Xiaomei; Bioorganic Chemistry; vol. 100; (2020);,
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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C2H3N3

Method B: 2-Fluoro-6-[1 ,2,3]triazol-2-yl-benzoic acid. To a 2 L, 3- necked, round-bottomed flask equipped with an overhead mechanical stirrer, thermocouple probe, heating mantle, reflux condenser, and nitrogen inlet were added 2-fluoro-6-iodobenzoic acid (127.6 g, 480 mmol), copper iodide (4.57 g, 24 mmol), and Cs2C03 (312.6 g, 959 mmol). To these solids were added dioxane (640 mL), then water (2.6 mL, 144 mmol), then 1 H-1 ,2,3-triazole (55.6 mL, 959 mmol), and finally frans-1 ,2-dimethylcyclohexane-1 ,2-diamine (15.1 mL, 96 mmol). The mixture was then warmed to 60 C for 30 min, then to 83 C for 30 min, and then to 100 C for 3 h. After the 3 h at 100 C, the mixture was cooled and then 1 L of MTBE and 1 L of water were added. After vigorous mixing, the layers were separated and the bottom aqueous layer was acidified to pH 1 .72 with -148 mL of concentrated hydrochloric acid. The aqueous was then extracted twice with EtOAc. The combined organic layers were dried over Na2S04, filtered, and concentrated to provide a dark oil. The oil was stirred overnight in EtOAc (450 mL) and the resulting precipitate was removed by filtration. The mother-liquors were concentrated to a brown solid (106.21 g, 75 wt% by quantitative HPLC, 79.7 g, 80%). 1H NMR (400 MHz, DMSO-d6): 8.22 – 8.13 (bs, 2H), 7.84-7.80 (m, 1 H), 7.74 – 7.65 (m, 1 H), 7.50 – 7.41 (m, 1 H).

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); 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. 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.45 g, 3.37 mmol, Intermediate 10: step d) was added THF (25 mL) and the solution was cooled to -75 C. n-BuLi (2.5 M in hexanes, 1.3 mL, 3.25 mmol) was added dropwise. After 2 minutes, 1-methyl-1H-1,2,3-triazole-5-carbaldehyde (580 mg, 5.22 mmol, Intermediate 18) in 3 mL THF was introduced. The reaction mixture was allowed to warm to -20 C. over 45 minutes at which time the reaction was quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (5*40 mL) and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (5% CH3CN-DCM increasing to 30% CH3CN +2% MeOH) afforded the title compound as an off white amorphous solid. 1H NMR (600 MHz, CDCl3) delta 8.15 (d, J=1.9 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.54 (dd, J=8.6, 2.0 Hz, 1H), 7.49 (d, J=8.2 Hz, 2H), 7.38 (d, J=8.1 Hz, 2H), 7.27 (s, 1H), 6.14 (d, J=4.6 Hz, 1H), 5.01 (s, 1H), 4.33 (s, 2H), 4.07 (s, 3H), 3.95 (s, 3H). MS (ESI): mass calcd. for C22H18ClF3N4O2, 462.1, m/z found 463.1 [M+H]+.

The synthetic route of 202931-88-2 has been constantly updated, and we look forward to future research findings.

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.; US2015/105372; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 41253-21-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 41253-21-8 name is Sodium 1,2,4-triazol-1-ide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Compound 271Synthesis of N-(5-(1H-1,2,4-triazol-1-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide; As shown in Reaction 1, first, magnesium was added to 1-bromo-3,4,5-trimethoxybenzene as a starting material. Then, Compound (VII) derivative was added thereto to obtain a compound [N-(5-fluoro-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide. Thus obtained compound [N-(5-fluoro-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide] (36.2 mg, 0.1 mmol) was dissolved in DMF (2 ml), and 1,2,4-triazole.Na (28.5 mg) was added thereto at room temperature. The mixture was heated with stirring for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with an EtOAc solution. The organic layer was washed with water, and brine. The extracted organic layer was dried over anhydrous MgSO4, and the solid substance was filtered off. The remaining solvent was removed by vacuum evaporation. The resulting residue was purified by column chromatography (SiO2, n-Hex/EA=2/1?1/1) to obtain Compound 271 (25.6 mg, 65%).1H NMR (CDCl3) delta 10.812 (s, 1H), 9.077 (s, 1H), 8.788 (s, 1H), 8.144 (s, 1H), 7.767 (d, J=8.36 Hz, 1H), 7.564 (d, J=8.52 Hz, 1H), 6.956 (s, 2H), 3.954 (s, 3H), 3.879 (s, 6H), 2.264 (s, 3H). MS (ESI) m/z 397 (M++H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Sodium 1,2,4-triazol-1-ide, and friends who are interested can also refer to it.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; US2009/275575; (2009); 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. 16681-72-4, name is 5-Bromo-1-methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Bromo-1-methyl-1H-1,2,4-triazole

[280] 1H-pyrazol-3-amine (305 mg, 3.671 mmol, 1.0 eq), 5-bromo-1-methyl-1,2,4-triazole (600 mg, 3.704 mmol, 1.01 eq), copper(I) bromide (106 mg, 0.739 mmol, 0.2 eq), cesium carbonate (1.26 g, 3.852 mmol, 1.05 eq), and N,N-dimethylformamide (2.2 mL) were combined. The reaction vessel was sealed and stirred overnight at 120 C. The mixture was diluted with dichloromethane and methanol, and the mixture was filtered though a layer of Celite. The filtrate was concentrated. The crude residue was purified by silica gel chromatography (linear gradient of 0-15% [2229] methanol/dichloromethane) to provide 1-(2-methyl-1,2,4-triazol-3-yl)pyrazol-3-amine (118 mg, 19% yield). 1H NMR (400 MHz, CDCl3) delta 7.99 (d, J = 2.7 Hz, 1H), 7.68 (s, 1H), 5.89 (d, J = 2.7 Hz, 1H), 4.18 (s, 3H), 3.91 (s, 2H) ppm. ESI-MS m/z calc. 164.08, found 165.23 (M+1).

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 16681-72-4.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARIFSON, Paul, S.; COME, Joh, H.; COURT, John, J.; GALE-DAY, Zachary; GU, Wenxin; JACKSON, Katrina, L.; MAGAVI, Sanjay, Shivayogi; NANTHAKUMAR, Suganthini, S.; RONKIN, Steven, Michael; SWETT, Rebecca, Jane; TANG, Qing; (383 pag.)WO2018/107056; (2018); 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methyl-1H-1,2,3-triazole

General procedure: 1-Methylimidazole (0.49 g, 6.05 mmol) was added to a stirred solution of Key Intermediate-1 (2.3 g, 4.03 mmol) in acetonitrile (25 mL) at RT. The reaction mixture was heated to 90 C for 16 h and concentrated under reduced pressure. The crude material was triturated with diethyl ether (2 x 10 mL) to afford a brown solid (2.4g) which was used in the next steps without further purification. M/z 616.38 (M)+ TFA: H2O (9:1, 20 mL) was added to the brown solid (2.4 g) at RT. The reaction mixture was stirred for 3 h and concentrated under reduced pressure. The resulting crude product was triturated with diethyl ether (2 x 5 mL) and dried under high vacuum. The crude product was purified by preparative HPLC affording the title product as off-white solid (515 mg, 30% over 2 steps).

According to the analysis of related databases, 16681-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Antabio SAS; DAVIES, David; LEIRIS, Simon; (56 pag.)EP3572411; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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 16681-70-2, HPLC of Formula: C3H3N3O2

Compound 2 (13 mg, 29 muiotaetaomicron) was dissolved in DIPEA (12 mu^, 69 muiotaetaomicron) and combined with the activated acid solution. The mixture was stirred at room temperature for 15 minutes, after which time LCMS indicated desired product formation. The solvent was removed in vacuo and the crude residue was purified by reverse phase chromatography to yield Compound b (0.8 mg) as a TFA salt. MS m/z [M+H]+ calc’d for C25H27CIF3N5O3, 538.18; found 538.

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; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 61-82-5, These common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, 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.

General procedure: A mixture of aromaticaldehyde (1.0 mmol) and dimedone(1.0 mmol) with 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1.0 mmol) was stirred in acetic acid (5 mL) at 60 Cfor the appropriate time (Tables 3, 4). The progress of thereaction was monitored by TLC. After completion of thereaction, a thick precipitate was obtained. The solid productwas filtered off and washed with acetic acid (3 ¡Á 2 mL) togive the pure products 4 and 6, and subsequently dried in air.The pure products were characterized by conventional spectroscopicmethods. Physical and spectral data for the compounds,4b, 4c, 4h, 4j, 6a, 6c, and 6h are represented below:

The synthetic route of 61-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Hazeri, Nourallah; Habibi-Khorassani, Sayyed Mostafa; Journal of the Iranian Chemical Society; vol. 12; 8; (2015); p. 1419 – 1424;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7343-33-1, name is 5-Bromo-1H-1,2,4-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 7343-33-1, Computed Properties of C2H2BrN3

To a mixture of 1 -iodo-4-(trifluoromethoxy)benzene (3 g, 10.416 mmol) in methylsulfinylmethane (24 mL) was added 3-bromo-1 H-1 ,2,4-triazole (3.1 g) under nitrogen atmosphere followed by addition of cesium carbonate (6.7 g, 20.833 mmol) and copper iodide (0.4 g, 2.083 mmol). The reaction mass was stirred at 130¡ãC for 18 hours in seal tube. The reaction mass was then diluted with water and extracted with ethylacetate (3 x 70 mL). The combined organic layers were then dried over sodium sulphate and concentrated under reduced pressure followed by column chromatography to obtain the title compound as solid (3 g). (0581) H NMR (400 MHz, (CD3)3SO): delta 9.38 – 9.25 (m, 1 H), 7.98 – 7.92 (m, 2H), 7.65 – 7.53 (m, 2H) LC/MS (method E) m/z: 308 [M + H]+, Rt = 0.94 min.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; JEANGUENAT, Andre; BENFATTI, Fides; RAWAL, Girish; (89 pag.)WO2018/15328; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics