Category: Triazoles

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

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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61-82-5, its application will become more common.

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

Reference of 16681-70-2, These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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.

B. (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid ethyl ester (R4=H; R7=-CH2CH3) 1,2,3-Triazole-4-carboxylic acid (11.5 mg, 102 nmol, 1.2 eq.) and HATU (38.6 mg, 102 nmol, 1.2 eq.) were dissolved in DMF (0.9 mL) and stirred at room temperature for 5 minutes. DIPEA (29.5 muL, 2.0 eq.) was added to yield the activated acid. (2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid (35 mg, 85 mumol, 1.0 eq.) was dissolved in EtOH and 4 M of HCl in dioxane (423 muL) was added. The mixture was heated to 60 C. overnight, then concentrated to dryness and purified by reverse phase chromatography (5-60% MeCN in water over 18 minutes. The clean fractions were combined and dried under vacuum to dryness, then combined with the activated acid. After 20 minutes, the reaction was quenched with water and the product was dried under vacuum and purified by preparative HPLC to yield the title compound (4 mg, >95% purity. MS m/z [M+H]+ calc’d for C24H28N4O4, 437.21. found 437.3.

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

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1001401-62-2, 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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

A mixture of A-1 (0.72 g, 3.8 mmol) and thionyl chloride (0.36 mL, 5.0 mmol) in toluene (7 mL) and a drop of DMF is heated to 60C for 2h, then cooled and concentrated. The residue is dissolved in 5 mL of dry DCM and added dropwise to a stirred mixture of C-1 (0.65 g, 4.64 mmol) and TEA (1 .44 mL, 10.3 mmol) in dry DCM (10 mL) at OC. The reaction is stirred at RT for 2h. Water is added and the organic layer is separated, washed with citric acid (10% aq. solution) and with NaHC03 (sat. aq. solution). The organic layer is dried and concentrated to provide 0.94 g of C-3. ESI-MS: 275.1 [M+H]+, HPLC (Rt): 0.69 min (method M)

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, 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; (70 pag.)WO2017/178338; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 4928-88-5, 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. 4928-88-5 name is Methyl 1H-1,2,4-triazole-3-carboxylate, 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.

In a 250 mL four-necked flask equipped with a mechanical stirrer, thermometer and distillation apparatus, 100.0 g of tetraacetyl ribose was added and heated to 100 ¡ã C in an oil bath.After the tetraacetyl ribose is completely melted into a transparent liquid, the stirring is started.40.0 g of methyl 1,2,4-triazolecarboxylate was added, and the two materials were uniformly mixed.Add 1.4g of elemental iodine, continue to raise the temperature to 115 ¡ã C, and keep warm for 2 hours.Then, vacuuming was started, and by-product acetic acid was distilled off; after 1 hour, the reaction was stopped, and the mixture was cooled to 70 ¡ã C or lower, 100 mL of methanol was taken, and the mixture was added to the flask, and the mixture was stirred to uniformly dissolve the material, and poured into a beaker. Allow to cool to room temperature,Precipitate solids, filter, wash, dry,Ribavirin intermediate[1-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester], yield 82percent (Based on tetraacetyl ribose, the same below.)

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

Reference:
Patent; Henan Academy Of Sciences High Technology Research Center; Zhang Jiaxiang; Guo Xiaozhan; Chen Tiantian; Wang Huafen; Ren Zhiyong; Gong Wei; Fu Yang; Jiang Lei; (10 pag.)CN109336937; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 252742-72-6,Some common heterocyclic compound, 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, molecular formula is C3H4ClN3O, 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.

A mixture of Example 87D (0.05 g, 0.126 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.132 ml, 0.757 mmol) in Nu,Nu-dimethylformamide (1 mL) was treated with Example 637A (0.020 g, 0.151 mmol) and the reaction was stirred at room temperature for 3 hours. Additional N-ethyl-N- isopropylpropan-2-amine (0.05 mL) and additional Example 637A (0.010 g, 0.076 mmol) were added and the mixture was stirred 3 hours longer. The reaction mixture was directly purified by reverse phase HPLC on a Phenomenex Luna C8(2) 5 um IotaOmicronthetaAlpha AXIA column (30 mm x 75 mm) eluting with a gradient of 10-70percent acetonitrile in 0.1 percent ammonium acetate/water to afford the title compound. lH NMR (500 MHz, DMSO-d6) delta ppm 2.44 – 2.52 (m, 2H), 2.64 (t, J = 5.8 Hz, 2H), 3.14 (q, J = 2.7 Hz, 2H), 3.40 (s, 2H), 3.73 (s, 3H), 6.19 (d, J = 2.1 Hz, 1H), 6.44 – 6.51 (m, 1H), 7.02 (d, J = 4.9 Hz, 1H), 7.14 – 7.32 (m, 3H), 8.18 (d, J = 4.9 Hz, 1H), 1 1.24 (s, 1H), 1 1.30 – 1 1.39 (m, 1H), 1 1.77 (d, J = 2.2 Hz, 1H). MS (ESI+) m/z 421.1(M+H)+.

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)-1H-1,2,4-triazol-5(4H)-one, its application will become more common.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, The chemical industry reduces the impact on the environment during synthesis 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

EXAMPLE 3 4,5-Dibromo-1H-1,2,3-triazole STR12 To a solution of 140 g (1.32 moles) of sodium carbonate in 650 ml of water was added 75 g (661 mmoles) of 1H-1,2,3-triazole-4-carboxylic acid. The resulting solution was subjected to the dropwise addition of 208 g (1322 mmoles) of bromine and then stirred overnight at room temperature. After cooling to 0 C., the reaction was adjusted to pH 4 with 12N hydrochloric acid causing precipitation of 147 g (98%) of 4,5-dibromo-1-H1,2,3-triazole as a white solid. The structure was confirmed by n.m.r. and I.R.

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, 1H-[1,2,3]Triazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Stauffer Chemical Company; US4596596; (1986); A;,
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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. name: 3,5-Dibromo-1H-1,2,4-triazole

3,5-dibromo-1H-1,2,4-triazole (419 mg, 1.85 mmol) was added to a solution of phenylboronic acid (300 mg, 2.46 mmol), pyridine (0.2 mL, 2.46 mmol), copper(II) acetate (335 mg, 1.85 mmol) and 3 A molecular sieves in dry DCM (8 mL) and stirred at 25 C overnight. Upon completion monitored by LC/MS, sat. NH4Cl (20 mL) was added to the reaction mixture which was then washed with water, the organic layers were then combined and concentrated. The crude product was purified by flash column chromatography eluting with 15-50% EtOAc in Pet. Ether to give 3,5-dibromo-1-phenyl-1,2,4-triazole (454 mg, 1.50 mmol, 60% yield). LC-MS (ES+, Method A): 1.74 min, m/z 304.0 [M+H]+

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1H-[1,2,3]Triazole-4-carboxylic acid

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 mumol), DIPEA (86.3 muL, 496 mumol) and HATU (47.1 mg, 124 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyl ester (50 mg, 120 mumol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product purified by preparative HPLC and lyophilized to yield the title compound (13 mg; purity 95%). MS m/z [M+H]+ calc’d for C29H30N4O4, 499.23. found 499.4.

According to the analysis of related databases, 16681-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, name is 3,5-Dibromo-1H-1,2,4-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 7411-23-6

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) or 3-chloro-1,2,4-triazole (300 mg, 2.9 mmol), o-quinone methide precursor 2 (2.9mmol), and K2CO3 (1.2 g, 8.7 mmol) were refluxed for 4 h in DMF (10mL). After completion of the reaction, the mixture was cooled, andpoured into H2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized.

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
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., Application In Synthesis of 1H-1,2,4-Triazol-5-amine

General procedure: A mixture of aromaticaldehyde (1.0 mmol) and dimedone(1.0 mmol) with 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1.0 mmol) was stirred in acetic acid (5 mL) at 60 Cfor the appropriate time (Tables 3, 4). The progress of thereaction was monitored by TLC. After completion of thereaction, a thick precipitate was obtained. The solid productwas filtered off and washed with acetic acid (3 ¡Á 2 mL) togive the pure products 4 and 6, and subsequently dried in air.The pure products were characterized by conventional spectroscopicmethods. Physical and spectral data for the compounds,4b, 4c, 4h, 4j, 6a, 6c, and 6h are represented below:

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

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Hazeri, Nourallah; Habibi-Khorassani, Sayyed Mostafa; Journal of the Iranian Chemical Society; vol. 12; 8; (2015); p. 1419 – 1424;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics