Category: Triazoles

Adding some certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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 7170-01-6. 7170-01-6

250A. 5-(3-Methyl-lH-l,2,4-triazol-l-yl)isoquinoline: A mixture of 5- bromoisoquinoline (0.500 g, 2.403 mmol), 3-methyl-lH-l,2,4-triazole (0.599 g, 7.21 mmol), K2C03 (0.996 g, 7.21 mmol), and Cul (0.458 g, 2.403 mmol) in MP (5.0 mL) was heated at 150 C overnight. The reaction mixture was cooled to room temperature, filtered through a plug of CELITE, filter cake washed with 10% MeOH/DCM, filtrate absorbed onto silica gel, purified by reverse phase prep. HPLC, and concentrated to give a white solid (80 mg, 16%). XH NMR (400MHz, methanol-d4) delta 9.43 (d, J = 0.7 Hz, 1H), 8.83 (s, 1H), 8.57 (d, J = 6.2 Hz, 1H), 8.35 (d, J = 8.4 Hz, 1H), 7.99 (dd, J = 7.3, 1.1 Hz, 1H), 7.90 – 7.81 (m, 2H), 2.55 (s, 3H) ppm. MS (ESI) m/z: 211 (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 3-Methyl-1H-1,2,4-triazole.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; SMITH, II, Leon M.; ORWAT, Michael J.; JEON, Yoon; CORTE, James R.; WO2014/160668; (2014); A1;,
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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 16681-65-5

Step 3: (S)-Methyl 3-(1 -methyl- 1H- 1 ,2,3-triazol-5-yl)-5-(phenyl(tetrahydro- 2H-pyran-4-yl)methyl)-5H-pyrido [3,2-bjindole-7-carboxylateA dry, N2 (g) flushed, 1 dram vial was charged with tetramethylammonium acetate (33.3 mg, 0.250 mmol), bis(triphenylphosphine)palladium dichloride (8.79 mg, 0.0130 mmol) and (S)-methyl 3 -bromo-5 -(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrido[3,2-b]indole-7-carboxylate (60.0 mg, 0.125 mmol). To this was added 1-methyl- 1H-1,2,3-triazole (20.8 mg, 0.250 mmol). The vial was again flushed with nitrogen. Tothis was added NMP (0.5 mL). The resulting mixture was stirred vigorously under a stream of nitrogen for 10 mm. The vial was placed in a pre-heated oil bath at 95 C and heated at that temperature overnight. The reaction was cooled to room temperature, diluted with EtOAc, washed with water (2X), then brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (100% EtOAc – 1%MeOH/EtOAc) to give 39.5 mg (66%) as an off-white solid. ?H NMR (500MHz, CDC13)o 8.61 (d, J1.6 Hz, 1H), 8.50 (s, 1H), 8.47 (d, J8.2 Hz, 1H), 8.10 (d, J=8.2 Hz, 1H),7.82 (s, 1H), 7.75 (s, 1H), 7.53-7.45 (m, 2H), 7.42-7.35 (m, 2H), 7.35-7.30 (m, 1H), 5.63(d,J10.7 Hz, 1H), 4.11-4.03 (m, 4H), 3.98 (s, 3H), 3.86 (dd,J=11.7, 3.0 Hz, 1H), 3.57(td,J=11.9, 1.7 Hz, 1H), 3.37 (td,J=11.9, 1.9 Hz, 1H), 3.22-3.09 (m, 1H), 2.11-2.01 (m,1H), 1.72-1.59 (m, 1H), 1.50-1.38 (m, 1H), 1.07 (d,J13.1 Hz, 1H). LCMS (M+H) =482.3.

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, Name is 1-Methyl-1H-1,2,3-triazole, 16681-65-5, 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.

l-Methyl-5-tributylstannanyl-lH-[l,2,3]triazole; To a solution of 1 -methyl- lH-[l,2,3]triazole (1.33 g, 16 mmol) in THF (20 mL) at -78 0C, was added dropwise n-BuLi (11 mL,1.6M, 18 mmol). The mixture was stirred at -78 0C for 2 h before addition of Bu3SnCl (4.75 mL, 17.6 mmol). The mixture was stirred at this temperature for 1 h and at r.t. for 1 h. The mixture was concentrated in vacuo and hexanes was added. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo to afford l-methyl-5-tributylstannanyl-lH- [l,2,33triazole (6.12 g, 82% yield) as a yellow syrup.

Statistics shows that 1-Methyl-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 16681-65-5.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/108591; (2006); 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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine, A new synthetic method of this compound is introduced below., 61-82-5

A mixture of aldehyde (1 mmol), dimedone (1 mmol), 3-amino-1,2,4-triazole (1 mmol), and [C4(H-DABCO)2][HSO4]4 (16 mg) washeated in an oil bath (90 C) under solvent-free conditions. Aftercompletion of the reaction, as identified by TLC, using n-hexane:EtOAc (7:3) as the eluent, 10 mL of water was added and stirredfor 10 min. The catalyst was dissolved in water and the solid wasfiltered off and washed with warm EtOH, to obtain the pure targetmolecule.

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:
Article; Safari, Niloufar; Shirini, Farhad; Tajik, Hassan; Journal of Molecular Structure; vol. 1201; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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.

A mixture of the formamidine from step 1 (304 mg) and 4-triazolylaniline (75 mg) in AcOH (2 ml) was heated to 125 for 1.5 h. After cooling, the mixture was diluted and basified with IN NaOH (20 ml). The resulting ppt was isolated by filtration and dried to give the title compound (136 mg, 71 %) as a yellow solid.1H NMR delta 10.07 (IH3 s), 9.28 (IH, s), 8.78 (IH, s), 8.62 (lH,s), 8.25 (IH, s), 8.16 (IH, d, J 8.85Hz), 8.07 (2H, d, J 8.85Hz), 7.86 (2H, d, J 8.85Hz), 7.82 (IH, d, J 8.85Hz), 7.47 (IH, d, J 1.9Hz), 7.38 (IH, dd, J 8.2, 1.9Hz), 7.03 (IH, d, J 8.85Hz) 4.32 (4H, s); LC-MS rt 2.35 m/z 423 ES+.

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; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, 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. 4928-87-4

Step 7: Preparation of ((lR,3s,5S)-3-(8-amino-3-(6-phenylpyridin-3-yl)imidazo[l,2-a]pyrazin- 6-yl)-8-azabicyclo[3.2.1]octan-8-yl)(4H-l ,2,4-triazol-3-yl)methanone A mixture of crude 6-((lR,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin- 3-yl)imidazo[l,2-a]pyrazin-8-amine from step 7, lH-l ,2,4-triazole-3-carboxylic acid (33.0 mg, 0.29 mmol), EDCI (92.9 mg, 0.49 mmol), 1-hydroxybenzotriazole (65.6 mg, 0.49 mmol) and DIEA (253 ul, 1.46 mmol) in DMF (5 mL) was stirred at room temperature for lh.Purification with prep-LC and conversion to HCl salt provided ((lR,3s,5S)-3-(8-amino-3-(6- phenylpyridin-3-yl)imidazo[l,2-a]pyrazin-6-yl)-8-azabicyclo[3.2.1]octan-8-yl)(4H-l ,2,4- triazol-3-yl)methanone as HCl salt: LCMS tR = 2.25 Min (10 min run, UV254nm). Mass calculated for, M+ 491.2, observed m/z 492.3 (M+H).

Statistics shows that 4928-87-4 is playing an increasingly important role. we look forward to future research findings about 1,2,4-Triazole-3-carboxylic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MENG, Zhaoyang; SIDDIQUI, M. Arshad; REDDY, Panduranga Adulla, P.; WO2013/16160; (2013); 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., 7170-01-6

Intermediate 585-(3-Methyl-1 H-1 , -thazol-1 -yl)pyrazine-2-carboxylic acidA mixture of methyl 5-chloropyrazine-2-carboxylate (0.75 g), K2CO3 (1 .8 g) and 3- methyl-1 H-1 ,2,4-triazole(1 .2 g) in N,N-dimethylformamide (6 mL) is heated to 100C overnight. Analysis of the crude mixture by LCMS shows saponified product. The product is acidified with 1 N HCI and the precipitate is filtered and washed with water and diethyl ether to afford the title compound. LC (method 20): tR = 1 .21 min; Mass spectrum (APCI): m/z = 206 [M+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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-88-0, Adding a certain compound to certain chemical reactions, such as: 288-88-0, name is 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 288-88-0.

Stage 79.3: 4-(1,2,4] Triazol-1-yl-benzaldehydeTo a solution of 6.44 ml (60 mmol) of p-fluorobenzaldehyde in 40 ml of pyridine, 4.14 g (60 mmol) of 1,2,4-triazole, 0.286 g (2 mmol) of copper(I)oxide and 9.12 g (66 mmol) of potasium carbonate are succesively added at r.t. After stirring for 18 h at 125 C., the reaction mixture is concentrated under reduced pressure. The residue is diluted with CHCl3 and filtered through celite. The filtrate is concetrated and purified by flash column chromatography on silica gel (eluent: n-Hexane:AcOEt=4:1?AcOEt only?AcOEt: MeOH=20:1) to give 4-[1,2,4] triazol-1-yl-benzaldehyde as major product and 4-[1,3,4] triazol-1-yl-benzaldehyde as minor product. 1H-NMR (400 MHz, CDCl3): 7.61 (d, 2H, J=8.56 Hz), 8.09 (d, 2H, J=8.56 Hz), 8.59 (s, 1H), 10.10 (s, 1H) (minor product); 7.91 (d, 2H, J=7.07 Hz), 8.05 (d, 2H, J=7.07 Hz), 8.16 (s, 1H), 8.69 (s, 1H), 10.07 (s, 1H) (major product).

According to the analysis of related databases, 288-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Novartis AG; US7138432; (2006); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

956317-36-5, Name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, 956317-36-5, 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.

To a suspension of 5-methyl-2-{2H-1,2,3-triazol-2-yl)benzoic acid (4.00 g, 19.7 mmol) in CH2CI2 (90 mL) cooled at 0 C was added DMF (76 mu, 0.98 mmol) and oxalyl chloride (2.15 mL, 24.6 mmol). The reaction was allowed to warm to ambient temperature and stirred for 3.5 h. The solution was concentrated in vacuo to provide 5-methyl-2-(2H-1,2,3- triazol-2-yl)benzoyl chloride as a yellow-orange oil which gave a mass ion (ES+) of 218.2. NMR 6 (ppm) (CDC13): 7.89 (2 H, s), 7.76 (1 H, d, J= 8.2 Hz), 7.59-7.60 (1 H, m), 7.48-7.50 (1 H, m), 2.48 (3 H, s).

Statistics shows that 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid is playing an increasingly important role. we look forward to future research findings about 956317-36-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2013/62857; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 6818-99-1, name is 3-Chloro-1,2,4-triazole, I believe this compound will play a more active role in future production and life. 6818-99-1

A solution of 4-[5-(6-chloro-3-ethylsulfonyl-2-pyridyl)-4-methyl-1 ,2,4-triazol-3-yl]-6-(trifluoromethyl) pyrimidine (300 mg, 0.693 mmol) and 3-chloro-1 H-1 ,2,4-triazole (107.6 mg, 1.04 mmol) in pyridine (3 ml) unter argon was heated in the microwave at 120C for 30 minutes. After cooling, the reaction mixture was poured onto iced water (20 ml), the suspension filtered and the solid washed with cold water. This residue was dissolved in dichloromethane, dried over sodium sulfate, filtered and concentrated to dryness to afford the title compound 4-[5-[6-(3-chloro-1 ,2,4-triazol-1-yl)-3-ethylsulfonyl-2- pyridyl]-4-methyl-1 ,2,4-triazol-3-yl]-6-(trifluoromethyl)pyrimidine (compound P48) as a solid, mp 261- 263C. LCMS (method 1 ): 500/502 (M+H)+; retention time: 0.96 min. H-NMR (CDCI3, ppm) 1.38 (t, 3H), 3.72 (q, 2H), 4.14 (s, 3H), 8.25 (d, 1 H), 8.73 (d, 1 H), 8.79 (s, 1 H), 9.07 (s, 1 H), 9.48 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 6818-99-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; EMERY, Daniel; BUCHHOLZ, Anke; (145 pag.)WO2017/16910; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics