Triazoles

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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 16681-70-2

[0635] Compound 1 (500 mg, 1.4 mmol) was combinedwith HATU (656 mg, 1.7 mmol), 3H-[1,2,3]triazole-4-carboxylicacid (195 mg, 1.7 mmol) and DMF (3 mL). DIPEA(803 f.LL, 4.6 mmol) was added and the mixture was stirred for30 minutes. Saturated aqueous NH4Cl (10 mL) and EtOAc(40 mL) were added. The organic layer was separated anddried over MgS04 . The solvent was evaporated and the residuepurified by normal phase chromatography (0-1 00%EtOAc/hexanes) to yield Compound 2 (650 mg).

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1338226-21-3,Some common heterocyclic compound, 1338226-21-3, name is 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one, molecular formula is C4H6ClN3O, 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 75L flask was charged a 9.63wt% solution of 3-(chloromethyl)-4-methyl-lH-l,2,4-triazol-5(4H)-one in NMP (1 1.6 kg, 7.55 mol), 3 -chloro-5 -((2-oxo-4-(trifluoromethyl)- 1 ,2-dihydropyridin-3 -yl)oxy)benzonitrile (2.00 kg, 6.29 mol), NMP (3.8 L) and 2-methyl-2-butanol (6.0 L). To the resulting suspension was slowly added N,N-diisopropylethylamine (4.38 L, 25.2 mol) over 4h. The reaction was aged 18h at ambient temperature. The reaction is considered complete when HPLC indicates <1% 3 -chloro-5 -((2-oxo-4-(trifluoromethyl)-l,2-dihydropyridin-3-yl)oxy)benzonitrile remaining. The tan solution was quenched with acetic acid (1.26 L, 22.0 mol) and aged at ambient temperature overnight. The tan solution was warmed to 70 C. Water (2.52 L) was added and the batch was seed with anhydrate Form II (134 g). The thin suspension was aged lh at 70 C. Additional water (14.3 L) was added evenly over 7 h. The slurry was aged 2h at 70 C and then slowly cooled to 20 C over 5 h. The slurry was filtered and washed with 2 : 1 NMP/water (6 L), followed by water washes (6 L x 2). The filter cake was dried over a 2 sweep to give 2.53 kg (85% yield - corrected) of a white solid that was confirmed to be crystalline Form II by X-ray powder detraction analysis. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one, its application will become more common. Reference:
Patent; MERCK SHARP & DOHME CORP.; ITOH, Tetsuji; JEON, Ingyu; MANGION, Ian; QIAN, Gang; SHERRY, Benjamin, D.; GAUTHIER, Donald, R.; CAO, Yang; WO2014/89140; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-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. Application In Synthesis of 5-Methyl-4H-1,2,4-triazol-3-amine

A mixture of methyl 3-oxo-2-(4-(4-(trifluoromethoxy)phenyl)piperidin-1 -yl)butanoate (46A) (300 mg, 0.835 mmol) and 3-methyl-1 H-1 ,2,4-triazol-5-am ine (123 mg, 1 .252 mmol) in acetic acid (10 mL) was heated at 130 C for 2 h . Then reaction mixture was diluted with water (20 mL), adjusted to pH=6 by addition of saturated Na2C03 solution and extracted with EtOAc twice. Organic layers were combined, dried over Na2S04 and concentrated to give a crude product, which was purified by ISCO with 0-1 00% EtOAc:EtOH (3:1 ) in hexanes to give two peaks of same mass. Peak two was the desired product based on NMR. 1 H NMR (400 MHz, DMSO-d6) delta 7.48 – 7.40 (m , 2H), 7.30 (dt, J = 7.8, 1 .1 Hz, 2H) , 3.49 (t, J = 11 .4 Hz, 2H), 2.87 – 2.74 (m , 2H), 2.74 – 2.60 (m , 1 H), 2.41 (s, 3H), 2.34 (s, 3H), 1 .87 – 1 .63 (m , 4H). Method 1 : RT = 1 .12 min. ; M/Z (M+H) = 408.1 .

The synthetic route of 4923-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHIANELLI, Donatella; GIBNEY, Michael; LERARIO, Isabelle K.; LIANG, Fang; LIU, Xiaodong; MOLTENI, Valentina; NAGLE, Advait Suresh; SMITH, Jeffrey M.; SUPEK, Frantisek; XIE, Yongping; YEH, Vince; (64 pag.)WO2018/229683; (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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 7170-01-6

General procedure: General method for preparation of all presented compounds is described below. Completion ofthe reactions was determined by TLC with bromocresol green solution as a stain.10 mmol of the appropriate azole (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole,3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole or 5-methyl-1H-tetrazole) and 10 mmol of 1-adamantanecarboxylic acid were placed in 20 mL screwcap vial and dissolved in 10 mL of 98% concentratedsulfuric acid. The mixture was cooled to 0 C using an ice bath. After cooling, 10 mmol (1010mg) of potassium nitrate were added in small portions over the period of 30 min. Once all of thenitrate has been added, the ice bath was removed, and the mixture was stirred for another 4 h atroom temperature. After 4 h of stirring, reaction mixture was poured on 100 g of crushed ice withshaking and allowed to stand until it reached room temperature. Quenched mixture was filtered andneutralized with saturated NaHCO3 solution. Precipitate was filtered, washed with copious amountsof distilled water and dried in vacuum desiccator. Products are suciently pure for the synthesis ofcoordination compounds, but for the analysis the small portions of each compound were recrystallizedfrom the mixture of water/MeOH (9:1).

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 7170-01-6.

Reference:
Article; Pavlov, Dmitry; Sukhikh, Taisiya; Filatov, Evgeny; Potapov, Andrei; Molecules; vol. 24; 15; (2019);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7411-23-6, name is 3,5-Dibromo-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 7411-23-6, Computed Properties of C2HBr2N3

Step B: Preparation of 3,5-dibromo-1H-1,2,4-triazole-1-acetic acid A solution of 3,5-dibromo-1H-1,2,4-triazole (i.e. the product of Example 15, Step A) (4.54 g, 20.0 mmol) in acetonitrile (20 mL) was treated with potassium carbonate (5.0 g) and ethyl bromoacetate (4.52 g, 27.0 mmol). The reaction mixture was heated at reflux for 4 h and then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (150 mL), filtered, washed with water, 1 N hydrochloric acid and saturated aqueous sodium bicarbonate, and dried (MgSO4). The resulting mixture was filtered and concentrated under reduced pressure to give 6.19 g of ester compound as a pale yellow oil. The ester compound in tetrahydrofuran (40 mL) was treated with 2 N aqueous sodium hydroxide (20 mL) and stirred at room temperature for 3 h. The reaction mixture was cooled in an ice bath and acidified with 6 N hydrochloric acid (10 mL). The resulting mixture was extracted with ether (200 mL), and the separated organic layer was washed with saturated aqueous sodium chloride, dried (MgSO4), filtered and concentrated to give 6.38 g of the title compound as a pale yellow oil. The crude product was triturated with hot n-butyl chloride (100 mL). The mixture was cooled to room temperature and filtered to give 3.77 g of the title compound as a white solid melting at 147-152 C. 1H NMR (CDCl3): delta 5.00 (s, 2H).

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, 3,5-Dibromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gregory, Vann; Pasteris, Robert James; US2010/240619; (2010); 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. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3,5-Dibromo-1-methyl-1H-1,2,4-triazole

In a 25 mL round bottomed flask, 3,5-dibromo-1-methyl-1H-1,2,4-triazole (Int-41, 536 mg, 2.23 mmol) was dissolved in DMF (4 mL) and potassium carbonate (615 mg, 4.45 mmol), followed by 4-fluoro-3-(trifluoromethyl)phenol (401 mg, 350 mu, 2.23 mmol) were added. The reaction mixture was stirred for 18 h at 100 C. After cooling, it was concentrated in vacuo, the residue was dissolved in dichloromethane (15 mL) and saturated aqueous solution of sodium carbonate (15 mL). Phases were separated, the aqueous layer was extracted with dichloromethane (2 x 15 mL), the combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, 20 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 50:50 v/v) to afford the title compound as white solid (737 mg, 97%). HPLC (method LCMS_fastgradient) tR= 1.28 min. 1H NMR (CDCl3, 300 MHz): delta 3.80 (s, 3 H), 7.23-7.31 (m, 1 H), 7.53-7.61 (m, 2 H). MS (ES+) m/z 340.0, 342.0 [M+H, Br isotopes].

The synthetic route of 23579-79-5 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

Synthetic Route of 288-36-8, 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. 288-36-8, name is 1H-1,2,3-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 0.87 g (8.4 mmol) of 2-chloroimidazole in 14 mL of DMF was added 0.40 g (10 mmol) of 60% NaH in mineral oil. After 20 min of stirring, 2.5 g (8.4 mmol) of 4-bromo-2-tert-butoxycarbonylamino-butyric acid methyl ester in 5 mL of DMF was added. The reaction mixture was heated to 80 C for 1 h. The mixture was diluted with EtOAc (150 mL), washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0-5% MeOH in CH2C12) to provide 2.1 g (78%) of 2-tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl- butyric acid methyl ester.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 6523-49-5, 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. 6523-49-5 name is 4-(1,2,4-Triazol-1-yl)aniline, 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 10-a (114 mg, 0.71 mmol) and compound 5 (100 mg, 0.24 mmol) were dissolved in n-butanol (2 mL), p-toluene sulfonic acid monohydrate (180 mg, 0.95 mmol) was added. The mixture was heated to 110 C. and stirred for 16 hours. After cooled to room temperature, the mixture was stirred for further 30 minutes, and there was solid precipitated. After filtration, the solid was purified by preparation HPLC (mobile phase:acetonitrile, water (0.05% trifluoroacetic acid); gradient: 60%-90%-10%) to give yellow solid T-10 (25 mg, yield: 19%). LC-MS (ESI): m/z=547 [M+H]+. (0164) 1H-NMR (400 MHz, CDCl3) delta: 8.58 (d, J=4 Hz, 2H), 8.41 (s, 1H), 8.13 (s, 1H), 8.09 (d, J=6 Hz, 1H), 7.92 (d, J=9 Hz, 2H), 7.71 (d, J=9 Hz, 2H), 7.49 (d, J=6 Hz, 1H), 4.66 (d, J=9 Hz, 2H), 4.25 (d, J=9 Hz, 2H), 3.45 (s, 2H), 3.10 (q, J=6 Hz, 2H), 1.43 (t, J=6 Hz, 3H) ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1,2,4-Triazol-1-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; SHANGHAI CHEMEXPLORER CO., LTD.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WANG, Tinghan; US2015/336982; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole, 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. Product Details of 22300-52-3

Step 1 : Cs2C03 (2.42 g, 7.43 mmol) is added to a stirred solution of A-28.2 (1 .68 g, 7.43 mmol) in dry DMF (10 mL). The mixture is stirred for 10 min before A-28.1 (1.00 g, 4.95 mmol), Cul (56.6 mg, 0.30 mmol) and A-28.3 (63.4 muIota_, 0.45 mmol) are added and the reaction is heated to 1 10¡ãC by microwave irradiation and stirred for 30 min. After cooling, the mixture is concentrated, poured into water and extracted with Et20. The organic phase is dried and concentrated to give the crude product which is purified by flash column chromatography on silica gel (using a solvent gradient from n-hexane/EA = 8/2 to EA 100percent) to provide 1.5 g of A- 28.4. ES+/-: 348 [M+H]+; HPLC (Rt): 0.57 min (Method P).

The synthetic route of 22300-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; (102 pag.)WO2017/178344; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 13273-53-5, These common heterocyclic compound, 13273-53-5, name is 4-Bromo-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.

To a solution of the crude (S)-4-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide (30 mg, 0.059 mmol) in residual dioxane was added 4-bromo-1-methyl-1H-1,2,3-triazole (14.24 mg, 0.088 mmol), PdCl2(dppf) (42.9 mg, 0.059 mmol), DME (195 mul) and 2 M Na2CO3 (130 mul) at room temperature. The reaction mixture was stirred for 5 h. After water and EtOAc were added, the organic layer was extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered off, and concentrated in vacuo. The crude product was purified by prep HPLC. The pure fractions were lyophilized yielding (S)-4-(2-amino-5-(1-methyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide as a TFA salt (25% over 2 steps). LCMS (m/z): 467.3 (MH+), 0.61 min; 1H NMR (400 MHz, CD3OD) delta ppm 8.64 (m, 1H), 8.31 (m, 1H), 8.25 (m, 2H), 8.2 (m, 1H), 7.82 (m, 1H), 7.4 (m, 3H), 7.28 (m, 2H), 7.22 (m, 1H), 5.11 (m, 1H), 4.07 (s, 3H), 3.78 (m, 2H).

The synthetic route of 13273-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics