Month: October 2020

7411-23-6, A common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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.

NaH (60 % dispersion in mineral oil; 5.29 g, 132 mmol) was added to a stirred solution of 3,5-dibromotriazole (20.0 g, 88.2 mmol) in DMF under an atmosphere of N2 at r.t.. After 30 min, 2-iodopropane (10.6 ml, 106 mmol) was slowly added and the r.m. was heated at 40 C for 2-3 h. The content was carefully poured onto ice/H20 (1 1), and the mixture was extracted with DIPE. The combined organic extracts were washed with H20 (4 x 200 ml), then with brine and dried (Na2S04). Filtration and concentration under reduced pressure yielded a yellow oil. Yield: 16.50 g of intermediate 24 (70 %).

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

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; VAN BRANDT, Sven, Franciscus, Anna; DE CLEYN, Michel, Anna, Jozef; GIJSEN, Henricus, Jacobus, Maria; BERTHELOT, Didier, Jean-Claude; SURKYN, Michel; WO2011/86099; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

956317-36-5, Adding some certain compound to certain chemical reactions, such as: 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, 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 956317-36-5.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1 ,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dirnethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to rt, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 50% EtOAc in water with 0.1% TFA) to give the desired A-3. A portion of this acid (0.1 1 g, 0.53 mmol) was treated with thionyl chloride (0.59 g, 5.3 mmol) in dichloromethane (5.0 mL) at rt. After stirring at RT for 1 h, the mixture was concentrated, azeotroping with benzene to yield acid chloride A-3.

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 956317-36-5.

Reference:
Patent; MERCK & CO., INC.; WO2009/11775; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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. 956317-36-5.

A mixture of compound 4a (100 mg, 0.49 mmol),compound 12 (100 mg, 0.47 mmol), HATU (268 mg, 0.71 mmol) and DIEA (182 mg,1.41 mmol) in DMF (10 mL) was stirred at r.t. for 3 h. The reaction mixture wasdiluted with water and extracted with EtOAc. The organic layers was concentratedand purified by flash column to give compound 5a (130 mg, yield: 69%). MS (ESI):m/z 398.3 [M + H]+

The synthetic route of 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Songliang; Sun, Yu; Hu, Yi; Zhang, Hongmei; Hou, Lijuan; Liu, Xing; Li, Yufeng; He, Haiying; Luo, Zhi; Chen, Yuan; Wang, Yuhe; Shi, Weihua; Shen, Liang; Cao, Changqing; Liang, Wei; Xu, Qing; Lv, Qiang; Lan, Jiong; Li, Jian; Chen, Shuhui; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1458 – 1462;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 584-13-4, name is 4H-1,2,4-Triazol-4-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 584-13-4. 584-13-4

General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

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 4H-1,2,4-Triazol-4-amine.

Reference:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 184177-83-1, name is 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, 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 184177-83-1, 184177-83-1

10 g of compound of formula A and 76 mL DMSO were added into a reaction flask at room temperature, and stirred until clarification. An alkaline solution previously prepared from 1.4 g sodium hydroxide and 6 g water was further added thereto. The mixture was stirred for 1 h. Then, 10 g of compound of formula IX was added thereto. The mixture was warmed up to 38 C. and reacted for 16 h. After the reaction was completed, the mixture was warmed up to 45 C. 6 mL water was added thereto. The mixture was stirred for 30-60 min. 154 mL water was further added thereto. The mixture was stirred for 1 h, and filtered under suction. The resultant solid was drip washed with 4¡Á50 mL purified water to obtain a wet product. (0249) The wet product and 60 mL of 90% aqueous ethanol solution were added to a reaction flask, warmed up to 65 C., and stirred. After clarification, 1.5 g active carbon was added thereto. The mixture was stirred for 15 min, filter-pressed while hot, and washed with 15 mL of 90% aqueous ethanol solution. Then, the filtrate was warmed up to 65 C., stirred, cooled to 40-45 C. after clarification, crystallized while keeping the temperature for 1 h, further cooled to 0-5 C., crystallized while keeping the temperature for 1 h, and filtered under suction. The resultant solid was first drip washed with 5 mL of 50% aqueous ethanol solution, and then drip washed with 4¡Á50 mL purified water. The solid was collected, placed in a ventilated oven at 50-55 C. and dried for 16 h to obtain 13.2 g of product.

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, 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Ausun Pharmaceutical Co., Ltd.; Zheng, Zhiguo; (23 pag.)US2019/71408; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common heterocyclic compound, 184177-83-1, name is 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, molecular formula is C30H35N5O3, 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. 184177-83-1.

To a 100 ml three-necked flask was added 2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one (4.78 g) and DMSO (40 ml)Stirring dissolved, A concentration of 25 wt% aqueous NaOH (1.6 ml) was added,Mixed for 10 minutes, (5R-cis)-4-toluenesulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester (4.4 g), The mixture was reacted at 30 C for about 14 h, Liquid phase monitoring to the reaction is completed, The reaction solution was poured into vigorously stirred water (240 ml) Plus, Stir again for 10min, filter, Filter cake washed with water, The filter cake was recrystallized from isopropanol to give a solid, Dried in vacuo to give an off-white powdery solid (Formula II); By NMR, mass spectrometry and infrared spectroscopy, The gray powder solid is a compound of formula II, And the purity of the compound is 99%.

The synthetic route of 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebei Guolong Pharmaceutical Co., Ltd.; Yan, Dianshu; Wei, Saili; Sun, Man; Yin, Jie; Liu, Yupu; Hu, Shuo; Wu, Yujie; (12 pag.)CN106366076; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, 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 7170-01-6 as follows.

A mixture of (E)-N-(2-bromophenyl)-3-(3-methoxy-4-prop-2-ynoxy-phenyl)prop-2- enamide (0.2 g, 0.517 mmol, 1.0 equiv.) (4), 3-methyl- lH-l,2,4-triazole (0.258 g, 3.11 mmol, 6.0 equiv.), cuprous iodide (0.049 g, 0.258 mmol, 0.5 equiv.) and cesium carbonate (0.506 g, 1.55 mmol, 3.0 equiv.) in dimethyl sulfoxide (2 mL) was stirred at 100 C under nitrogen in microwave for 3 hours. The mixture was cooled to 25C, diluted with ethyl acetate (20 mL) and filtered. The filtrate was concentrated under reduced pressure to give a residue which was purified by preparative HPLC to give the desired product as a light yellow solid (5 mg, 2%); 1H NMR (CDCI3, 400 MHz) delta 9.89 (s, 1H), 8.63 (d, = 8.0 Hz, 1H), 8.37 (s, 1H), 7.64 (d, = 16.0 Hz, 1H), 7.46 (t, = 8.0 Hz, 1H), 7.35 (d, = 8.0 Hz, 1H), 7.21 (t, = 8.0 Hz, 1H), 7.15 (d, = 8.0 Hz, 1H), 7.08 – 7.05 (m, 2H), 6.36 (d, = 16.0 Hz, 1H), 4.82 (d, = 2.0 Hz, 2H), 3.94 (s, 3H), 2.60 (s, 3H), 2.55 (t, = 2.0 Hz, 1H); MS (ESI+) m/z 389.1 (M+H)+; 99% purity, RT 2.34 min (Method 8).

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHIRE HUMAN GENETIC THERAPIES, INC.; MILLER, Thomas; PAPAIOANNOU, Nikolaos; (243 pag.)WO2018/144620; (2018); A1;,
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. 6818-99-1, name is 3-Chloro-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 6818-99-1

2- [6-Chloro-3- (ethanesulfonyl) pyridin-2-yl] -3-methyl-6-[(trifluoromethyl) sulfanyl]-3H-imidazo [4,5-b] pyridine 200 mg, 60% sodium hydride (oily) 37 mg, and a mixture of 2 mL of DMF, was added under ice-cooling 3-chloro-1H-1,2,4-triazole 67 mg. After the mixture was stirred under ice-cooling for 2.5 hours, a saturated aqueous solution layer was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and saturated brine, and dried with anhydrous sodium sulfate. The resulting organic layer was dried under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 171mg of the compound of the present invention beta38 referred to below.

The synthetic route of 6818-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; NAKAJIMA, YUJI; OKAWARA, YUICHI; (263 pag.)JP2016/102104; (2016); A;,
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. 288-88-0, name is 1H-1,2,4-Triazole, This compound has unique chemical properties. The synthetic route is as follows., 288-88-0

General procedure: A dry flask was charged with the nitrogen containing heterocycles (1.5 mmol), aryl halides (1 mmol), potassium carbonate(2 mmol) and CuMeSal (0.01 mmol) then anhydrous DMSO (5 ml) was added. The reaction mixture was stirred at 110C, open to air, for 3h , cooled to room temperature, filtered, and the precipitate was washed with DMSO (2 ml) then stirred with ice water (30 ml) and extracted with ethyl acetate (3 ¡Á 50 ml),dried over sodium sulfate and the solvent was removed under reduced pressure.The residue was purified by chromatography or recrystallization as indicated with each compound.

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; Farahat, Abdelbasset A.; Boykin, David W.; Tetrahedron Letters; vol. 55; 19; (2014); p. 3049 – 3051;,
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. 7411-23-6

To a solution of 3,5-dibromo-1H-1,2,4-triazole (10 g, 44.1 mmol) in acetonitrile (100 mL) was added 2-(2-bromoethoxy)tetrahydro-2H-pyran (8.0 mL, 52.9 mmol) and N,N-diisopropylethylamine (8.45 mL, 48.5 mmol). The mixture was stirred at 90 C. for 3 h and concentrated under reduced pressure. The residue was diluted with ethyl acetate (300 mL), washed saturated sodium bicarbonate (2*50 mL), brine (2*50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 20% ethyl acetate in petroleum ether) to afford 3,5-dibromo-1-(2-tetrahydropyran-2-yloxyethyl)-1,2,4-triazole (13 g, 83%) as a colorless oil, used as is in the next step.

Statistics shows that 7411-23-6 is playing an increasingly important role. we look forward to future research findings about 3,5-Dibromo-1H-1,2,4-triazole.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; Zhao, Guiling; Chen, Huifen; (100 pag.)US2018/153831; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics