Triazoles

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

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

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

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

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

61-82-5, 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.

General procedure: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

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:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

423165-07-5, Name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, 423165-07-5, 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.

The amine of formula VII (0.29 g, 1.25 mmol), alcohol of formula XVII (0.45 g, 1.2 equivalents), [Cp*lrl2]2(0.036 g, 2.5 mol%), sodium iodide (0.019 g, 5 mol%) and molecular sieves (0.75 g) were suspended in 10 ml of toluene at the room temperature, the reaction mixture was bubbled (2 to 5 min) with argon and closed with a septum. The reaction mixture was heated up to 120C and stirred for 24 hours. Then, the mixture was cooled down to 50C, activated carbon (Norit A, 0.03 g) was added and the suspension was stirred for 15 minutes. The suspension was filtered through kieselguhr and washed with dichloromethane (30 ml). Removal of the solvent by distillation at a reduced pressure provided a crude mixture containing 67.8 % of Maraviroc of formula I (determined by UPLC).

Statistics shows that exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane is playing an increasingly important role. we look forward to future research findings about 423165-07-5.

Reference:
Patent; ZENTIVA, K.S.; CERNA, Igor; HAJICEK Josef; WO2014/173375; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 4314-22-1, name is 2-(1H-1,2,3-Triazol-1-yl)acetic acid, I believe this compound will play a more active role in future production and life. 4314-22-1

Step C N-Methoxy-N-methyl-2-(1-(1, 2, 3-triazolyl)) acetamide Oxalyl chloride (0.95 mL, 11 mmol) was added dropwise to a suspension of 2- (1-1, 2,3-triazolyl)) acetic acid (Step B, 1.27 g, 10 mmol) in 10 mL CH2C12 containing 0.05 mL DMF. Vigorous effervescence was observed. This mixture was stirred at room temperature for 4 h and cooled to-78C. A solution of N. O- dimethylhydroxylamine hydrochloride (1.2 g, 13 mmol) and diisopropylethyl amine (6.0 mL, 35 mmol) in 10 mL CH2C12 was added slowly over 3 min. The mixture was then allowed to warm to room temperature and stirred overnight. The reaction mixture was then diluted with ether until no additional precipitate appeared. The solid was filtered and washed with ether. The filtrate was concentrated and the residue was purified on silica gel using EtOAc as solvent to provide the title compound as amorphous solid.

The chemical industry reduces the impact on the environment during synthesis 4314-22-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2005/44785; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

584-13-4, name is 4H-1,2,4-Triazol-4-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. 584-13-4

The synthetic pathways for the preparation of target compounds 1-9 and 24-41 are depicted in FIG. 2. We synthesized compounds 1-9 using a straightforward strategy, which involved the Grignard reactions of 2,4-difluoro-alpha-(1H-1,2,4-triazolyl)acetophenone with different alkyl magnesium bromide in the presence of magnesium bromide ethyl etherate. Compounds 24-41 were prepared in three steps. 4-Amino-1,2,4-triazole was reacted with various 2-haloacetophenone in refluxing isopropanol to give 10-16 in excellent yields (88-96%). Compounds 10-16 were conveniently deaminated by NaNO2 in aqueous HCl at room temperature. The desired products 17-23 were precipitated after neutralization of the reaction with potassium carbonate. The precipitates were collected by filtration and washed with water to afford pure products. No further purification was required because the excess of reactants was soluble in water and removed by filtration.

Statistics shows that 584-13-4 is playing an increasingly important role. we look forward to future research findings about 4H-1,2,4-Triazol-4-amine.

Reference:
Patent; University of Kentucky Research Foundation; Garneau-Tsodikova, Sylvie; Shrestha, Sanjib K.; Garzan, Atefeh; Chandrika, Nishad Thamban; (54 pag.)US2018/194742; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, These common heterocyclic compound, 16681-65-5, name is 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.

1-methyl-1H-1,2,3-triazole was prepared according to the literature reference WO2008/98104. To a 2 L flask containing 1-methyl-1H-1,2,3-triazole (9 g, 108.3 mmol) was added THF (1500 mL) and the solution was cooled to -40 C. To this colorless homogeneous solution was added n-butyllithium (2.5 M in hexanes, 45 mL, 112.5 mmol) dropwise which immediately afforded a dark brown viscous mixture. The mixture was kept between -10 to -20 C. for 60 minutes, then a THF solution of 2,4-dimethylthiazole-5-carbaldehyde (17.2 g, 121.8 mmol in 200 mL THF) was introduced via cannula. Once the aldehyde was added the reaction was allowed to warm to room temperature. After 3 hours, the reaction was quenched by pouring into a saturated solution of aqueous NH4Cl. The aqueous portion was extracted with EtOAc in portions, 7*400 mL. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a brown oil. Chromatography on silica gel (10% acetone-DCM increasing to 50% acetone and increasing to 10% MeOH-DCM) provided the title compound as an amber solid.

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 16681-65-5.

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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics