Triazoles

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. 6818-99-1 name is 3-Chloro-1,2,4-triazole, 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. 6818-99-1

A solution 2-(5-bromo-3-ethylsu lfanyl-2-pyridyl)-5-cyclopropyl-3-methyl-6-(trifluoromethyl)im idazo[4 , 5- c]pyridin-4-one A4 (Prepared as described before, 150 mg, 0.3169 mmol) in N,N-dimethylformamide (0.3169 mL)was added 3-chloro-1H-1,2,4-triazole (36.09 mg, 0.3486 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (2.822 mg, 0.00341 mL, 0.03169 mmol), potassium carbonate (8.760 mg, 0.064 mmol) and copper(l) iodide (3.018 mg, 0.01585 mmol). The reaction mixture was stirred at reflux overnight. Same quantity of N,N-dimethylethylenediamine, copper(l) iodide and potassium carbonate were added at the mixture and the mixture was stirred at 120C overnight The reaction mixture was filtered through an Hyflo pad, which was rinsed with methanol, then the reactionmixture was concentrated under vacuum. The residue was subjected to column chromatography over silica gel, eluting with ethyl acetate I cyclohexane. The selected fractions were evaporated to yield the title compound (30% yield). LC-MS(Method A): RT 1.08, 476 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; MUEHLEBACH, Michel; HALL, Roger, Graham; (106 pag.)WO2017/89190; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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 6523-49-5. 6523-49-5

Example 96 (3-Methyl-1H-pyrazolo[4,3-c]pyridin-4-yl)-(4-1,2,4-triazol-1-yl-phenyl)-amine hydrochloride salt. Intermediate 3 (50 mg, 0.3 mmol), 4-1,2,4-triazol-1-yl-phenylamine (95 mg, 0.60 mmol) and concentrated hydrochloric acid (27 mul, 0.39 mmol), were dissolved in n-butanol (1.1 ml). The reaction mixture was irradiated at 19O0C for 45 minutes in a Biotage I-60 microwave reactor. The mixture was evaporated, dissolved in DMSO (1 ml), filtered, washed with water and dried to give the desired product as a pale green solid (46 mg, 47%). 1H NMR (400 MHz, 6O0C, DMSO-d6) delta ppm 2.75 (s, 3 H), 7.14 (d, J=7.3 Hz, 1 H), 7.56 (d, J=6.9 Hz, 1 H), 7.73 (d, J=9.2 Hz, 2 H), 8.02 (d, J=9.2 Hz, 2 H), 8.25 (s, 1 H), 9.32 (s, 1 H), 9.99 (s, 1 H). m/z (ES+APCI)+: 292 [M+H]+

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 4-(1,2,4-Triazol-1-yl)aniline.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; MCIVER, Edward, Giles; SMILJANIC, Ela; HARDING, Denise, Jamilla; HOUGH, Joanne; WO2010/106333; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below.

Take 0 ¡¤ 15g (0.31 mmol)The intermediate 27 was dissolved in 30 ml of CHCl, and 0 ¡¤ lg (0.52 mmol) of EDCI was added to obtain 0.2 g (0.27 mmol) of 1,2,4-triazol-3- Formic acid, stirred at room temperature12h, TLC detection. The reaction was completed and the crude product was dried and purified by silica gel column chromatography (eluent: methanol / dichloromethane / aqueous ammonia = 50:500: 1,7: ?: ?) to give a white solid. Example 21 Target product 0.1 g Yield 55.5%

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; Beijing Foreland Pharma Co., Ltd; Zhang, Xingmin; Wang, Ensi; Niu, Shengxiu; Guo, Jing; Dai, Zhuolin; Zheng, Nan; Ji, Qi; Li, Qinyan; Liang, Tie; (109 pag.)CN104411706; (2016); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

In a 250 mL round bottomed flask, 3,5-dibromo-1H-1,2,4-triazole (Int-1, 2.00 g, 8.82 mmol) was dissolved in DMF (60 mL) and potassium carbonate (2.72 g, 19.5 mmol) was added. The resulting suspension was stirred for 20 min at room temperature. Then, 2,2-difluoroethyl trifluoromethanesulfonate (2.08 g, 1.29 mL, 9.7 mmol) was added and the reaction mixture was stirred for 6 h at room temperature. After that, it was concentrated in vacuo, the residue was diluted with MTBE (100 mL) and ice water (100 mL), the aqueous phase was extracted with MTBE (3 x 100 mL). The combined organic layers were washed with water (2 x 100 mL) and brine (1 x 100 mL), dried (sodium sulfate) and concentrated in vacuo. The resulting crude product, a white solid, was used in the next step without further purification (2.402 g, 94 %). HPLC (method LCMS_fastgradient) tR = 0.88 min. 1H NMR (CDCl3, 300 MHz): delta 4.52 (dt, J = 4.2, 12.6 Hz, 2 H), 6.16 (tt, J= 4.2, 54.8 Hz, 1 H). MS (ES+) m/z 289.9, 291.9, 293.9 [M+H, 2 Br isotopes] .

The synthetic route of 3,5-Dibromo-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 956317-36-5, name is 5-Methyl-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. 956317-36-5

21.3g (105mmol) of 5-methyl -2- (2H-1,2,3- triazole -2-) benzoic acid was suspended in isopropyl acetate (230mL) was added 2.2mL of DMF, in a nitrogen atmosphere, was slowly added 15.3g oxalyl chloride, control the deflation rate, maintaining the reaction temperature at 20-25 , after the reaction became a clear solution, distilled under reduced pressure at not more than 30 , only to the remaining 100 ml of volume, then add 230 ml of isopropyl acetate, and then the solvent was evaporated to only 100 ml of this solution was added 450 ml of isopropyl acetate to give 5-methyl -2- (2H- 1,2,3-triazole -2-) benzoyl chloride solution.

The chemical industry reduces the impact on the environment during synthesis 956317-36-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; China Resources Double-Crane Pharmaceutical Co., Ltd.; Liu, kaixiang; Zhou, Yisui; Li, Kai; (20 pag.)CN105330657; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, 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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1H-1, 2, 3-triazole (10 g, 145 mmol) in anhydrous THF (150 mL) was added powder K2CO3(40.0g, 290 mmol) , then iodomethane (32.29 g, 227 mmol) was added dropwise at 30 . After the addition was complete, the mixture was stirred at 30 for 16 h. The reaction mixture was filtered and the filtrate was concentrated to afford the product as an oil.1H-NMR: (DMSO-d6400MHz) delta 8.06 (s, 1H) , 7.71 (s, 1H) , 4.05 (s, 3H)

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; 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

61-82-5, name is 1H-1,2,4-Triazol-5-amine, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 61-82-5

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:

Statistics shows that 61-82-5 is playing an increasingly important role. we look forward to future research findings about 1H-1,2,4-Triazol-5-amine.

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

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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 7411-23-6

Intermediate 4 3,5-Dibromo-l-methyl-lH-l,2,4-triazole To a solution of 3,5-dibromo-lH-l,2,4-triazole (1.0 g, 4.41 mmol) in DMF (9 mL) sodium tert- pentoxide (0.485 g, 4.41 mmol) was added and the mixture was stirred for 10 min at rt under nitrogen atmosphere, lodomethane (0.29 mL, 4.63 mmol) was added and the mixture was stirred at 40C for 2 hours. The mixture was poured onto water and extracted twice with diisopropylether. The organic phase was washed with water (2x), brine and dried over sodium sulfate. The solvents were evaporated to give the title compound as a solid (0.83 g, 78%).

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

Reference:
Patent; ACTURUM LIFE SCIENCE AB; BESIDSKI, Yevgeni; YNGVE, Ulrika; PAULSEN, Kim; LINDE, Christian; NORDVALL, Gunnar; MACSARI, Istvan; MALMBORG, Jonas; WO2014/195321; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, Name is 3,5-Dibromo-1H-1,2,4-triazole, 7411-23-6, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

A mixture of 3,5-dibromo-1H-1,2,4-triazole (700 mg, 3.1 mmol), 2,2′-bipyridyl (60 mg, 0.39 mmol), copper(II) acetate (140 mg, 0.77 mmol), potassium carbonate (852 mg, 6.2 mmol) and cyclopropylboronic acid (795 mg, 9.3 mmol) was dissolved in toluene (5 mL) and water (1.5mL) and stirred at 70 C for 18 h. The reaction mixture was cooled to RT, quenched with NH4Cl (sat. aq.) and the products extracted in DCM. The combined organic fractions were dried with a phase separator and reduced in vacuo. The crude mixture was dissolved in DCM and dry-loaded onto silica. Purification via silica column chromatography eluting with 10-60% EtOAc in Pet. Ether afforded 5-dibromo-1-cyclopropyl-1,2,4-triazole and 1-allyl-3,5-dibromo-1,2,4-triazole (123 mg, 0.46 mmol, 15% yield) as an inseparable mixture. UPLC-MS (ES+, Method A): 1.52 min, m/z 267.9 [M+H]+

Statistics shows that 3,5-Dibromo-1H-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 7411-23-6.

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

41253-21-8, A common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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.

Preparation of 4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidine-1-carboxylic acid tert-butyl ester (5): To a solution of 4-cyclohexyl-4-methansulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (39 g, 103.8 mmol) in N,N-dimethylformamide (200 mL) is added sodium triazole (38 g, 415.2 mmol). The resulting solution is heated to 100 C. for 24 hours then cooled to room temperature. The solvent is removed under reduce pressure and the crude product purified over silica (80:20 EtOAc:hexane) to afford 28.7 g (79.7% yield) of the desired compound as a colorless solid. 1H NMR (CD3OD) delta0.95-1.90 (m, 15H), 1.46 (s, 9H), 3.45-3.55 (m, 4H), 4.34 (s, 2H), 7.99 (s, 1H), 8.48 (s, 1H). MS (ESI) m/z 349, (M+H+), 371(M+Na+)

The synthetic route of 41253-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ebetino, Frank Hallock; Liu, Xuewei; Solinsky, Mark Gregory; Wos, John August; Mumin, Rashid Naeem; US2004/10010; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics