Triazoles

Adding some certain compound to certain chemical reactions, such as: 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, 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 4922-98-9. 4922-98-9

6.02.04.37 5-bromo-3-phenyl-lH-(l, 2, 4) triazole 115 mL bromine hydro acid was added to 9.5 g 5-phenyl-2H-(l, 2, 4) triazol-3-ylamine and 12.3 g sodiumnitrite at -5¡ãC. The reaction was warmed to RT and refluxed for 20 min. Then the mixture was cooled and basicfied with sodiumdicarbonate and extracted with ethyl acetate. The organic layer was dried and evaporated to give 11 g of the desired product. Rt: 1.07 min (method B), (M+H)+: 223/225

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 5-Phenyl-1H-1,2,4-triazol-3-amine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WO2013/107761; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

To a reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and 3- phenylpropan-l- amine (0.30 mL, 2.1 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into iced water and extracted with DCM (2 x 50 mL). The DCM phase was washed with ice cold water (2 x 100 mL). The DCM phase was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and chromatographed on silica gel using EtOAc as eluents to get the desired amide 15 (69.7 mg, 15 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.63 (br s, 1H), 8.68 (br s, 1H), 8.42 (br s, 1H), 7.30-7.18 (m, 5H), 3.40-3.24 (m, 2H), 2.61 (t, J= 7.6 Hz, 2H), 1.87-1.78 (m, 2H) ppm. MH+ = 231.3 m/z. At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2,4-Triazole-3-carboxylic acid, and friends who are interested can also refer to it. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); 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

To a mixture of 3-methyl- lH- l,2,4-triazole (330 mg, 3.97 mmol), 5-chloro-2-fluoro- benzaldehyde (425 mg, 2.68 mmol) in DMSO (5.0 mL) is added K2C03 (725 mg, 5.25 mmol). The reaction mixture is stirred at 100 C for 2 hours. The reaction mixture is allowed to cool to room temperature, diluted with CH2C12 (100 mL), and washed with H20 (75 mL x2). The organic layer is dried with Na2S04 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 5% MeOH in EtOAc as the eluent to afford an impure mixture of 5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-benzaldehyde plus regiosiomer (270 mg).To a mixture of 4-(2-amino-pyrimidin-5-yl)-Nl-ieri-butyl-benzene-l,2-diamine (270 mg, 1.05 mmol) and impure mixture of 5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-benzaldehyde plus regiosiomer (270 mg) in DMF (15.0 mL) is added Oxone (650 mg, 1.06 mmol) in H20 (5.0 mL). The reaction mixture is stirred at room temperature for 1.5 hours and then quenched with saturated sodium thiosulfate aq. (25 mL). The quenched reaction mixture is extracted with EtOAc (25 mL x2) and the combined organic layers are washed with H20 (50 mL x2), dried with Na2S04 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 5% MeOH in CH2C12 as the eluent to afford an impure mixture of 5-(2-amino- pyrimidin-5-yl)- l-ieri-butyl-2-[5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-phenyl]-2,3- dihydro-lH-benzimidazol-2-ol plus regiosiomer (25 mg).

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; CHEN, Zhidong; HAO, Ming-Hong; LIU, Weimin; LO, Ho-Yin; LOKE, Pui Leng; MAN, Chuk, Chui; MORWICK, Tina, Marie; NEMOTO, Peter, Allen; TAKAHASHI, Hidenori; TYE, Heather; WU, Lifen; WO2011/68821; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

81606-79-3, 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. 81606-79-3, name is 2-(1,2,4-Triazol-1-yl)acetonitrile, A new synthetic method of this compound is introduced below.

To the solution of 3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]benzaldehyde (1223. OOmg, 4.62mmol) , Toluene (2.5mL), Triethylamine (L95mL, l3.87mmol) was added 2-(lH- l,2,4-Triazol-l-yl)acetonitrile (874.9lmg, 8.09mmol) . The resulted mixture was microwaved at 150 degrees for 3 h. LCMS was shown some product and still had some remained starting material. The reaction mixture was worked up with water (50 mL) and DCM (50 mL x 2). The organic layer was brined and dried with MgS04. The concentrated crude was purified by prep HPLC Shimadzu to obtain 3-[3-[2- [tert-butyl(dimethyl)silyl] oxycthy I ] phenyl ] -2-( 1 ,2,4-triazol- 1 -yl)prop-2-enenitrile ( 120.00mg) with 7.3 % yield. LC-MS m/z: 355[M+l]

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; PRINCIPIA BIOPHARMA INC.; LOU, Yan; OWENS, Timothy Duncan; BRAMELD, Kenneth Albert; GOLDSTEIN, David Michael; (171 pag.)WO2019/99576; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

89292-91-1, The chemical industry reduces the impact on the environment during synthesis 89292-91-1, name is 5-(4-Methylpiperazin-1-yl)-1H-1,2,4-triazol-3-amine, I believe this compound will play a more active role in future production and life.

General procedure: A solution of aminotriazole 11a-m (3.1mmol), glacial acetic acid (5mL), and diethyl ethoxymethylenemalonate (4.6mmol) was refluxed for 3h. After cooling to room temperature, the resulting precipitate was collected by filtration, washed with cold water and dried. The residue was stirred with cold ethyl ether (20mL) and filtered to afford the desired product. Following general procedure C, compound 12k was isolated as a white solid. Yield 78%, mp=220C dec. 1H NMR (200MHz, DMSO-d6) delta: 9.95 (br s, 1H); 8.41 (s, 1H); 4.17-4.07 (q, J=7Hz, 2H); 3.78-3.45 (m, 4H); 2.76 (s, 3H); 2.52-2.49 (m, 4H); 1.26-1.19 (t, J=7.2Hz, 3H)

The chemical industry reduces the impact on the environment during synthesis 5-(4-Methylpiperazin-1-yl)-1H-1,2,4-triazol-3-amine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Aghazadeh Tabrizi, Mojgan; Baraldi, Pier Giovanni; Ruggiero, Emanuela; Saponaro, Giulia; Baraldi, Stefania; Poli, Giulio; Tuccinardi, Tiziano; Ravani, Annalisa; Vincenzi, Fabrizio; Borea, Pier Andrea; Varani, Katia; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 11 – 27;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics