Triazoles

Electric Literature of 41253-21-8,Some common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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.

Ethyl chloroformate (13g) was slowly added dropwise to the solvent of triazole sodium salt (9.1g) in tetrahydrofuran (30mL) at 20-30 C, and the reaction was completed at 20-30 C for 1h. After the reaction is completed, filter to obtain a solution of ethyl 1,2,4-triazole-1-carboxylate in tetrahydrofuran; from -40 to -30, slowly add a solution of ethyl 1,2,4-triazole-1-carboxylate in tetrahydrofuran. A solution of LDA (lithium diisopropylamide) in tetrahydrofuran (2M, 60mL) was added dropwise. After reaction for 30min, ethyl chloroformate (13g) was added dropwise. After stirring for 30min, the temperature was slowly raised to 20-30 C and stirred for 2h; After completion, add 30% aqueous sodium hydroxide solution to the system and react at 80 90 for 2h. After completion of the reaction, cool to 0 10 , add hydrochloric acid to adjust pH 2 3, and filter to obtain 1, 2, 4-triazole -3-carboxylic acid, yield 82%.

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

Reference:
Patent; Shanghai Dongyue Pharmaceutical Co., Ltd.; An Na; Liu Xinke; Long Zhongzhu; Cai Chang; Cai Shuihong; (5 pag.)CN110903255; (2020); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 4928-88-5, 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. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 2 Preparation of methyl 1-(2,3,5-tri-O-Acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate Using a Mixture of beta/alpha-1,2,3,5-Tetra-O-acetyl-L-ribofuranose A 2 L flask was charged with 80.5 g of triazolemethylester, the above dichloromethane solution of beta/alpha-1,2,3,5-Tetra-O-acetyl-L-ribofuranose, and 37 g of acetic anhydride at ambient temperature.The mixture was distilled at atmospheric pressure (bath temperature, 90¡ã C.).When the pot temperature reached 85¡ã C. and the distillation became very slow, vacuum was applied (up to 30 mbar) and the distillation was continued for 40 minutes at 90¡ã C. (bath temperature) and then for another 40 minutes at 120¡ã C. (bath temperature, the pot temperature reached 117¡ã C.).The vacuum was released and 843 mg of triflic acid was slowly added.After the addition the vacuum was restored and the mixture was stirred at 115+-5¡ã C. (pot temperature) for 4 h.Upon the completion of the reaction the mixture was cooled to 70¡ã C. and to it was added 750 ML of 2B alcohol (ethyl alcohol).When a homogeneous solution was formed the mixture was cooled to 50¡ã C. and held until heavy precipitation formed (seeding might be necessary).The mixture was then slowly cooled to -5¡ã C. (bath temperature) in 2 h and held for at least 2 h.The solid was filtered, washed with 100 ML of cold 2B Alcohol (ethyl alcohol), and dried under vacuum at 50¡ã C. for 17 h to give 192.7 g (75.1percent yield from L-ribose) of methyl 1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate as an off-white solid.

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

Reference:
Patent; Dong, Zhiming; Zhang, Pingsheng; US2004/34213; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27808-16-8, name is 4-Methyl-1H-1,2,3-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 27808-16-8, Recommanded Product: 4-Methyl-1H-1,2,3-triazole

A solution of 4-methyl-iH-i,2,3-triazole (500 mg,6.02 mmol), 2,3-dichloro-5-nitropyridine (1277.42 mg, 6.62 mmol), K2C03 (2491.22 mg, 18.05 mmol) in CH3CN (5 mE) was stirred at it for 12 h. The mixture was concentrated under reduced pressure, the crude product was purified by colunm chromatography over silica gel (petroleum ether ethyl acetate from 20:1 to 1:1). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford i25a (1.1 g, 76.3%) as a yellow solid. ECMS (ESI) mlz M+i: 239.7.

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, 4-Methyl-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, 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. name: 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: Dimedone (0.14 g, 1 mmol), benzaldehyde (0.1 g, 1 mmol), and 4-phenylurazole (0.177 g, 1 mmol) were mixed with PEG-SO3H (0.6 g, 0.1 mmol) and the obtained mixture was stirred magnetically at 80 C for 40 min. After the completion of the reaction warm water (20 mL) was added and the mixture stirred for about 5 min. The insoluble crude product was filtered and recrystallized from EtOH/H2O 4:1 and the pure product was obtained (0.352 g, 91%). In order to recover the catalyst, the filtrate was dried under reduced pressure and recovered catalyst was washed with diethyl ether and reused after drying under reduced pressure. The equivalent procedure was used for the synthesis of triazolo[1,2-a]indazole-tetraones.

The synthetic route of 15988-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasaninejad, Alireza; Zare, Abdolkarim; Shekouhy, Mohsen; Tetrahedron; vol. 67; 2; (2011); p. 390 – 400;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 16681-70-2, 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 16681-70-2 as follows.

[0430] IH-1,2,3-triazole-4-carboxylic acid (15.9 mg, 141f.tmol) and HATU (53.5 mg, 141 f.tmol) were dissolved in DMF (2 mL) and stirred for 15 minutes at room temperature.(2R,4R)-4-Amino-2-azido-5-(5′-chloro-2′-fluorobiphenyl-4-yl)pentanoic acid ethyl ester (50 mg, 128 f.tmol) and DIPEA(67 f.LL, 384 f.tmol) were added, and the mixture was stirred atroom temperature for 15 minutes then concentrated in vacuoand the residue was dissolved in EtOH (2 mL). An aqueoussolutionoflNNaOH (1.3 mL, 1.3 mmol)was added, and themixture was stirred at room temperature for 30 minutes thenconcentrated in vacuo and the residue was purified by reversephase chromatography to yield Compound 1 ( 45 mg).

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 BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4922-98-9, A common heterocyclic compound, 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, molecular formula is C8H8N4, 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.

6.02.04.37 5-bromo-3-phenyl-1H-(1,2,4)triazole 115 mL bromine hydro acid was added to 9.5 g 5-phenyl-2H-(1,2,4)triazol-3-ylamine and 12.3 g sodiumnitrite at -5¡ã C. 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 By using the same synthesis strategy as for 5-bromo-3-phenyl-1H-(1,2,4)triazole the following compound was obtained:

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; Boehringer Ingelheim International GmbH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; US2013/184248; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1001401-62-2,Some common heterocyclic compound, 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, molecular formula is C9H7N3O2, 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 the product from step 5 (50 mg, 0.17 mmoi), FIATU (95 mg, 0.25 mmol), TEA (0.3 mL) and 2-.(2fi-J,234riazoi-2y1)benzoic acid (34.8 mg, 0.18 mmoi) in DMF (2 mL) was stirred at RI for 9 hours under the N2 atmosphere. Then the mixture was poured into water(5 rnL x 3) and extracted with EtOAc (5 mL x 3). The combined organic layer was washed withbrine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue waspurified by Prep?HPLC to give the title compound (30 mg) as yellow oil, LRMS m/z (M¡ÂH)471.1 found, 471.1 required.

The synthetic route of 1001401-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 956317-36-5, The chemical industry reduces the impact on the environment during synthesis 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, I believe this compound will play a more active role in future production and life.

General procedure: 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(WSCHCl) (37.4 g, 0.20 mol) was added to a solution of Nethyl-2[3-(5-fluoro-pyridin-2-yl)-1H-pyrazol-1-yl] ethanaminedihydrochloride (50 g, 0.16 mol), 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (33.9 g, 0.18 mol), 1-hydroxy-1H-benzotriazolehydrate (HOBtH2O) (26.4 g, 0.20 mol) and triethylamine (TEA)(39.5 g, 0.39 mol) in THF (500 mL) at 0 C, followed by stirring atroom temperature for 20.5 h. The solvent of the reaction solutionwas distilled off under reduced pressure. An aqueous NaHCO3 solutionand EtOAc were added to the resulting residue, followed byextraction with EtOAc. The organic layer was washed with water,and the solvent was distilled off under reduced pressure to yieldthe crude product (72 g). An additional 196.7 g of the crude productwas synthesized using the same method from N-ethyl-2[3-(5-fluoro-pyridin-2-yl)-1H-pyrazol-1-yl] ethanamine dihydrochloride(140 g, 0.46 mol) and 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoicacid (94.8 g, 0.50 mol). The obtained crude product (268.7 g) wasrecrystallized with heptane and EtOAc. The deposited solid wasthen collected by filtration. The obtained solid was dried by heatingunder reduced pressure to yield the title compound 27e as acolorless powder (217.3 g).

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

Reference:
Article; Suzuki, Ryo; Nozawa, Dai; Futamura, Aya; Nishikawa-Shimono, Rie; Abe, Masahito; Hattori, Nobutaka; Ohta, Hiroshi; Araki, Yuko; Kambe, Daiji; Ohmichi, Mari; Tokura, Seiken; Aoki, Takeshi; Ohtake, Norikazu; Kawamoto, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1260 – 1275;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 6523-49-5, These common heterocyclic compound, 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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.

4-Chloro-6-iodoquinazoline (WO9609294 Al , 150 mg) was treated with 4- triazolyl aniline (28 mg, 1 eq) in MeCN and refluxed for 6 h. Cooled overnight and filtered to give the title compound (70 mg).1R NMR delta 11.75 (IH, br s), 9.4 (2H, s), 9.04 (IH, s), 8.43 (IH, d, J 8.85Hz),8.34 (IH, s), 8.0(4H, m), 7.82 (IH, d, J 8.85Hz); LC-MS rt 2.32 m/z 415 ES+.

Statistics shows that 4-(1,2,4-Triazol-1-yl)aniline is playing an increasingly important role. we look forward to future research findings about 6523-49-5.

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

Related Products of 13273-53-5, A common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, 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.

A solution of 4-bromo-1-methyl-1H-1,2,3-triazole (5 g, 30.87 mmol), tert-butyl prop-2-enoate (11.9 g, 92.85 mmol), palladium acetate (1.1 g, 4.90 mmol), tri-o-tolylphosphane (1.9 g, 6.24 mmol) and triethylamine (4.7 g, 46.45 mmol) in N,N-dimethylformamide (50 mL, 646.09 mmol) was stirred for 12 h at 110 C. The resulting mixture was cooled to room temperature and then diluted with water. The resulting solution was extracted with ethyl acetate, dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under vacuum. The residue was purified by flash chromatography on a silica eluted with ethyl acetate/petroleum ether (3/2) to afford tert-butyl (2E)-3-(1-methyl-1H-1,2,3-triazol-4-yl)prop-2-enoate (3.6 g, 17.23 mmol) as a yellow solid. LCMS (ESI) [M+H]+=210

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; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics