Category: Triazoles

7170-01-6, 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. 7170-01-6 name is 3-Methyl-1H-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.

EXAMPLE 102 [2-Chloro-4-(3-methyl-1,2,4-triazol-1-yl)-phenyl](5H,11H-pyrrolo[2,1-c]-[1,4]benzodiazepin-10-yl)-methanone To a suspension of 60% sodium hydride in oil (0.3 g) in dimethylformamide (50 ml) was added dropwise 3-methyl-1,2,4-triazole (0.45 g). After hydrogen gas evolution ceased, 2-chloro-4-fluorophenyl-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-yl)-methanone (1.70 g) was added and the reaction mixture was heated in a sand bath at 110 C. for 18 hours. The mixture was poured onto ice, diluted with brine, and extracted with dichloromethane. The combined extracts were dried over anhydrous sodium sulfate and filtered through a short column of anhydrous sodium magnesium silicate. The solution was concentrated in vacuo and the residue was triturated with diethyl ether to give 1.25 g of the title compound as colorless crystals, m.p. 191-193 C., MS m/z: 404.1 (M+H)+.

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

Reference:
Patent; Wyeth; US6511974; (2003); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-88-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 4928-88-5 as follows.

EXAMPLE 6 A mixture of methyl 1,2,4-triazole-3-carboxylate (26.4 g, 0.21 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (60.2 g, 0.19 mole) was melted and then 0.36 g (0.01 eq.) of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 5 hours, while maintaining the temperature of the reaction mixture at 95+-5¡ã C. And then, the reaction mixture was crystallized with 300.8 me of methanol to give 58.9 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 81percent).

According to the analysis of related databases, 4928-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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. 61-82-5.

General procedure: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-1,2,4-Triazol-5-amine, its application will become more common.

Reference:
Article; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 61-82-5

General procedure: A mixture of 1,2,4-triazol-3-amine 1 (1 mmol), aromatic aldehydes2a-o (1 mmol) and 1,3-cyclohexanedione 3 (1 mmol) were taken into a RB flask, irradiated under MW at 150 W for 60 s. The progress ofthe reaction was observed by TLC. After cooling, the reaction mass becamegummy,washed thoroughlywith 1:1 hexane and ethyl ethanoateto afford the compounds 4a-o (Scheme 1).

The synthetic route of 61-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sompalle, Rajesh; Arunachalam, Prabhakarn; Roopan, Selvaraj Mohana; Journal of Molecular Liquids; vol. 224; (2016); p. 1348 – 1357;,
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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., 16681-65-5

n-BuLi (1.23 M in hexanes, 447 muL, 0.55 mmol) was added dropwise to a stirred slurry of 1-methyl-1,2,3-triazole (46 mg, 0.55 mmol) in THF (1 mL) at -40 C. under nitrogen. After stirring for 30 minutes at -40 C., the mixture was treated dropwise with a solution of (2,4-dichloro-3-isopropoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (104 mg, 0.27 mmol, Intermediate 25) in THF (1 mL). The reaction was allowed to warm to room temperature over 1 hour. The reaction was then quenched with saturated aqueous NH4Cl. The mixture was poured into a separatory funnel and extracted with DCM (2*25 mL). The organics were combined, washed with brine, dried (Na2SO4), filtered and concentrated to dryness to afford an orange-brown foam. The crude material was purified by FCC (1-7.5% MeOH/DCM) followed by reverse-phase HPLC (acetonitrile/water+0.05% TFA) to provide the title compound as a clear colorless oil. 1H NMR (500 MHz, CDCl3) delta ppm 8.23-8.20 (m, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.52-7.48 (m, 1H), 7.24 (s, 1H), 6.40 (s, 1H), 4.80-4.73 (m, 1H), 3.92 (s, 3H), 3.63 (s, 3H), 2.58 (s, 3H), 1.44-1.41 (m, 6H). MS (ESI): mass calcd. for C21H22Cl2N6O2, 460.1. m/z found, 461.1 [M+H]+.

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; JOHNSON & JOHNSON; 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.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, 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.

To prepare nano-sized [Mn(L)2(H2O)2] (1), 50ml solution of manganese(II) chloride tetrahydrate (0.1molL-1) in water was positioned in a high-density ultrasonic probe, operating at 40kHz with a maximum power output of 305W. Into this solution water a 50ml solution of the ligand 1H-1,2,4-triazole-3-carboxylic acid (0.1molL-1) and potassium hydroxide (0.01molL-1) were added dropwise. The obtained precipitates were filtered off, washed with water and then dried in air. m.p.>300C.

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:
Article; Safarifard, Vahid; Morsali, Ali; Ultrasonics Sonochemistry; vol. 21; 1; (2014); p. 253 – 261;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-34-2, 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. 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

A mixture of Zn(NO3)2¡¤6H2O (60 mg, 0.2 mmol), HCOONa¡¤2H2O (14 mg, 0.1 mmol), Hdmtz(19 mg, 0.2 mmol), an aqueous dimethylamine solution (0.3 mmol, 33percent), and H2O (3 ml) was placed in a Teflon-linedstainless steel vessel (12 ml), heated at 120 ¡ãC for 72 h, and then cooled to room temperature at a rate of 5 ¡ãC/h. Colorlessblock crystals of 1 were collected by filtration, washed with water, and dried in air to afford 22 mg (62percent based on Zn) of theproduct. Anal. calcd. for C13H22N10O8Zn4 (percent): C 22.06, H 3.13, N 19.79. Found (percent): C 22.12, H 3.09, N, 19.82. IR(KBr, cm?1): 3476(m), 1612(s), 1527(m), 1451(m), 1385(m), 1340(m), 1129(w), 1036(w), 881(w), 772(w), 700(w), 546(m).

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

Reference:
Article; Fang; Yang; Dou; Zhu; Xu; Journal of Structural Chemistry; vol. 59; 6; (2018); p. 1450 – 1455; Zh. Strukt. Kim.; vol. 59; 6; (2018); p. 1503 – 1507,5;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Under ice-water bath, 39.4 mg (0.349 mmol)1,2,4-triazole-3-carboxylic acid and 16.28 mg (0.426 mmol)2- (7-azobenzotriazole) -Nu, Nu, N, N-tetramethyluronium hexafluorophosphate was dissolved in 5 mL of dichloromethane(0.96 mmol) of triethylamine was added, and after stirring at 0 C for 30 minutes, 100 mg (0.194 mmol) of intermediate 130 was added,Stir the temperature overnight. TLC, after the completion of the reaction, 10 mL of saturated aqueous sodium bicarbonate solution was added, stirred for 20 minutes, separated, the aqueous phaseExtraction with methylene chloride, combined organic phase, dry, spin dry to obtain crude. The crude product was purified by preparative silica gel plate (dichloromethane / AAlcohol = 10/1, V / V) to give 10 of the title compound as a white solid in a yield of 8.4%

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; 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

A common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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. 288-36-8.

To a 20 ml microwave vial containing 2-bromo-4,5-dimethoxybenzoic acid (3 g, 1 1 .5 mmol), copper iodide (0.04 g, 0.5 mol%), cesium carbonate (7.5 g, 23 mmol), triazole (1 .33 mL, 23 mmol) and finally (R,R)-(-)-N,N’-dimethyl-1 ,2- cyclohexanediamine ligand (0.36 mL, 2.3 mmol) was added DMF (12 mL). The resulting clumpy yellow slurry was stirred until evenly dispersed then heated to 120C for 10-20 min using a microwave. At this point the reaction mixture appeared as a blue slurry which was then diluted with 20 mL ether and 20 mL H2O. The resulting solution was thoroughly stirred and transferred to a seperatory funnel then the RBF was subsequently rinsed with 20 mL ether and H2O each. The aqueous layer was separated from the organic layer and acidified to pH 1 with 6 mL cone. HCI. The now brown/ lime green aqueous layer was extracted twice with EtOAc. The bright yellow organic layers were combined and dried with Na2SO4 and then cone, into a yellow powder under reduced pressure which was purified by FCC (0-5% MeOH in DCM w/ 0.5% AcOH) to afford 2,3-dimethoxy-6-[1 ,2,3]triazol-2-yl-benzoic acid (60%) and 2,3- dimethoxy-6-[1 ,2,3]triazol-1 -yl-benzoic acid (20%). Data for 2,3-dimethoxy-6- [1 ,2,3]triazol-2-yl-benzoic acid, MS (ESI): mass calculated for CnHnN3O4, 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.87 (s, 2H), 7.47 (s, 1 H), 7.18 (s, 1 H), 3.94 (s, 3H), 3.91 (s, 3H).; Intermediate 80: 2,3-Dimethoxy-6-[1 , 2, 3]triazol-1 -yl-benzoic acid.The title compound was isolated from the procedure used to prepareIntermediate 79 with a 20% yield. MS (ESI): mass calculated for Cn Hn N3O , 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.17 (d, J = 1 .0 Hz, 1 H), 7.82 (d, J = 1 .0 Hz, 1 H), 7.62 (s, 1 H), 7.09 (s, 1 H), 3.95 (s, 3H), 3.91 (s, 3H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, 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.

Intermediate W (75 mg, 0.15 mmol) was dissolved in NMP (841 muL) before HATU (75 mg, 0.20 mmol), 1H-1,2,4-triazole-3-carboxylic acid (21 mg, 0.18 mmol) and N-ethyl-N-isopropyl-propan-2-amine (105 muL, 0.60 mmol) were added. The solution was stirred at room temperature for 1h before aq. NH4Cl was added and the aq. phase was extracted twice with EtOAc. The combined organic phase was washed with sat.aq. NaHCO3 and brine, dried over MgSO4, filtered and the filtrate evaporated under reduced pressure. The residue was purified flash chromatography on silica gel eluting with 0-100% EtOAc: Hexanes affording the title compound. (7-(tert-Butyl)-5-(4-fluoro-3- methylphenyl)furo[3,2-b]pyridin-2-yl)(2,2-dimethyl-4-(1H-1,2,4-triazole-3- carbonyl)piperazin-1-yl)methanone (17 mg, 21% yield). 1H NMR (400 MHz, DMSO-d6) 8.68 (s, 1H), 8.07 – 7.99 (m, 1H), 7.94 (ddd, J = 8.0, 5.2, 2.4 Hz, 1H), 7.71 (d, J = 8.5 Hz, 1H), 7.48 (d, J = 9.8 Hz, 1H), 7.22 (td, J = 9.1, 3.7 Hz, 1H), 4.48 (s, 1H), 4.10 – 3.61 (m, 6H), 2.31 (t, J = 2.5 Hz, 3H), 1.61 – 1.39 (m, 15H). Signals doubled due to amide rotamers. ESI-MS m/z calc.518.2442, found 519.09 (M+1)+; Retention time: 3.30 minutes using method A

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; VERTEX PHARMACEUTICALS INCORPORATED; SAYEGH, Camil Elie; STURINO, Claudio; FOURNIER, Pierre-Andre; LACOSTE, Jean-Eric; DIETRICH, Evelyne; MARTEL, Julien; VALLEE, Frederic; (494 pag.)WO2016/154075; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics