Triazoles

Related Products of 135242-93-2,Some common heterocyclic compound, 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, molecular formula is C4H7N3O, 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.

To a solution of 0.5 g (4.42 mmol, 1.0 eq.) of (l-methyl-li/-l,2,4-triazol-3-yl)methanol (Xlla) in 20 mL of acetonitrile was added 1.07 g (6.63 mmol, 1.5 eq.) of I,G -carbonyl and the mixture was stirred at room temperature for 2 h. Volatiles were removed in vacuo and the residue was resuspend in 20 mL of water. The mixture was extracted with 3 x 50 mL of 5% methanol in methylene chloride. The combined organic extracts were washed with 50 mL of sat. sodium carbonate solution, followed by 50 mL of brine, dried (T^SCL), filtered and the solvent was removed in vacuo to provide 0.77 g of ( 1 -methyl- 1 H- 1 2.4-triazol-3-yl)methyl 1 //-imidazole- 1 -carboxy late (XIHa).

The synthetic route of 135242-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; KULTGEN, Steven; COLE, Andrew G.; (217 pag.)WO2020/23710; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, molecular formula is C2H2BrN3, 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. SDS of cas: 7343-33-1

Step 1: 3-Bromo-1-(4-methoxybenzyl)-1H-1,2,4-triazole A mixture of 3-bromo-1H-1,2,4-triazole (10.0 g, 67.6 mmol), 1-(chloromethyl)-4-methoxybenzene (10.6 g, 67.6 mmol), DIPEA (17.5 g, 135 mmol) and potassium iodide (5.61 g, 33.8 mmol) in acetonitrile (300 mL) was stirred at 65¡ã C. for 120 min. The solvent was evaporated in vacuo and the residue was purified via flash chromatography on silica gel (solvent gradient: 0-30percent ethyl acetate in petroleum ether) to yield 12.9 g (71percent) of the title compound as a white solid. LCMS (ESI): [M+H]+=268/270.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7343-33-1, its application will become more common.

Reference:
Patent; Genentech, Inc.; Braun, Marie-Gabrielle; Garland, Keira; Hanan, Emily; Purkey, Hans; Staben, Steven T.; Heald, Robert Andrew; Knight, Jamie; Macleod, Calum; Lu, Aijun; Wu, Guosheng; Yeap, Siew Kuen; (183 pag.)US2018/65983; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

Preparation of N’-t-butyl-N-(1,2,3-triazole-4-carbonyl)-N’-(3-methylbenzoyl)hydrazine 1,2,3-triazole-4-carboxylic acid (1.0 g) and triethylamine (0.9 g) were dissolved in 40 ml methylene chloride and cooled in an ice bath. Methanesulfonylchloride (1.0 g) was added dropwise. After addition was complete, the reaction mixture was stirred for 0.5 hours. N’-t-butyl-N’-(3-methylbenzoyl)hydrazine (1.84 g) in 10 ml CH2 Cl2 was added dropwise. The resulting mixture was allowed to stand for 14 hours. Aqueous sodium bicarbonate was added. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to give a yellow oil. Chromatography on silica gel using acetone as eluant afforded N’-t-butyl-N-1,2,3-triazole-4-carbonyl-N’-(3-methylbenzoyl)hydrazine.

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US6013836; (2000); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 74205-82-6, These common heterocyclic compound, 74205-82-6, name is (1H-1,2,4-Triazol-1-yl)methanol, 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.

Example4. Synthesis of Intermediate 5Intermediate 4 (16.3g, 70.4 mmol) was completely dissolved in concentrated sulfuric acid (80ml) under ice bath, and triazolemethanol (10.4g) was added. The solution was stirred at room temperature for 5hrs. TLC was used toshow the completion of raw materials. Post-treatment: the reaction solution wasslowly added to 20% sodium hydroxide solution under ice bath. After alkalizing,dichloromethane was added to extract the product. The organic layer was driedand the solvent was removed by rotary evaporation. 21.2g yellow oil product(crude) was obtained. 15.6g light yellowsemi-solid (Intermediate 5) was obtained after column chromatography separation(dichloromethane: methanol 20: 1+ 1% triethylamine) and rotary evaporation,with a yield of 71.0%.

The synthetic route of 74205-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Wu, Yong; Hai, Li; Sun, Baohou; He, Yi; Li, Xiaocen; (11 pag.)CN103664900; (2016); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 103755-58-4, 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. 103755-58-4 name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, 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.

General procedure: Into a round bottom flask was added 5.71mmolof triazole type 12 or 21a in 50mL of dry THF, 17.13mmolof sodium hydride and 57.1mmolof alkyl bromide. The mixture was heated to reflux, and reaction progress was monitored by TLC. Subsequently, the solvent was evaporated and the mixture was extracted with ethyl acetate, washed with distilled water (3¡Á100mL) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the product was purified via silica-gel column chromatography using a gradient mixture of hexane-ethyl acetate, to afford the pure derivatives 14a-g and 23a-b.

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

Reference:
Article; Gonzaga, Daniel; Senger, Mario Roberto; Da Silva, Fernando De Carvalho; Ferreira, Vitor Francisco; Silva Jr., Floriano Paes; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 461 – 476;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 584-13-4, 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. 584-13-4 name is 4H-1,2,4-Triazol-4-amine, 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.

General procedure: To the solution of 4-amino-4H-1,2,4-triazole (0.0059 mol, 0.500 g) in an hydrous acetonitrile (20 mL), an N-alkyl or N-arylisothiocyanate (0.0065 mol) was introduced, and the obtained mixture was stirred at room temperature for 16h. Then the solvent was evaporated. The main compound was isolated from the reaction mixture by column chromatography (CHCl3: CH3OH; 9.5:1 vol.) or crystallized from acetonitrile.

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

Reference:
Article; Bielenica, Anna; Kedzierska, Ewa; Fidecka, Sylwia; Maluszynska, Hanna; Miroslaw, Barbara; Koziol, Anna E.; Stefanska, Joanna; Madeddu, Silvia; Giliberti, Gabriele; Sanna, Giuseppina; Struga, Marta; Letters in drug design and discovery; vol. 12; 4; (2015); p. 263 – 276;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 22300-52-3, 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. 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

To a 20-L round- bottom flask were placed 4,5-dibromo-2H-1,2,3-triazole (500 g, 2.20 mol), DCE (5 L), 2-methylfuran (5 L), cyclopropylboronic acid (379 g, 4.41 mol), Cu(OAc)2(401 g, 2.20 mol), 2,2-bipyridyl (344 g, 2.21 mol) and sodium carbonate (467 g,4.41 mol). The mixture was stirred overnight at 80 ¡ãC. After the reaction was cooled to room temperature, the mixture was filtered. The filtrate was concentrated under vacuum, dissolved in 5 L of EtOAc, washed with 2×1 L of 1 N hydrogen chloride and then with lxi L of brine, dried over sodium sulfate(Na2SO4), and concentrated under vacuum to afford the product.

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

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong R.; CHO, Aesop; BUENROSTRO, Ana Zurisadai Gonzalez; HAN, Xiaochun; JABRI, Salman Y.; MCFADDEN, Ryan; QI, Yingmei; VOIGT, Johannes; YANG, Hong; XU, Jie; XU, Lianhong; (545 pag.)WO2019/75291; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15294-81-2, name is 4,5-Dibromo-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 15294-81-2, Product Details of 15294-81-2

Intermediate 14e (0554) 4,5-Dibromo-2-methyl-2H-l,2,3-triazole Batch 1 : To a solution of 4,5-dibromo-lH-triazole (Intermediate 14f; 490.00 g, 2.16 mol) in DMF (3.2 L) was added potassium carbonate (358.23 g, 2.59 mol). The mixture was cooled to -10¡ãC under a nitrogen atmosphere and iodomethane (147.91 mL, 2.38 mol) was added dropwise. The reaction was then stirred at 25¡ãC for 16 hours. Batch 2: To a solution of 4,5-dibromo-lH-triazole (Intermediate 14f; 400 g, 1.76 mol, 1.00 eq) in DMF (2.8 L) was added potassium carbonate (291.9 g, 2.11 mol). The mixture was cooled to – 10¡ãC under a nitrogen atmosphere and iodomethane (131.48 mL, 2.11 mol) was added dropwise. The reaction was then stirred at 25¡ãC for 16 hours. Batches 1 and 2 were then combined and the reaction was quenched by the addition of water (4.2 L) and the aqueous phase extracted with MTBE (7 L x 3). The organic extract was concentrated under vacuum to approximately 700 mL and isopropanol (2 L) was added dropwise. This mixture was then stirred at 25 ¡ãC for 2 hours and the resulting precipitate filtered and dried under vacuum to afford undesired 4,5-dibromo-l-methyltriazole (220 g, 23.5percent) as a solid which showed the following NMR spectral data: FontWeight=”Bold” FontSize=”10″ H NMR (400MHz, CDCb) delta 4.09 (s, 3H). 13CNMR (400MHz, CDCb) delta 123.03, 113.09, 37.00. The filtrate was concentrated under vacuum to afford an oil, isopropanol (1 L) was added and resulting solution was warmed to 50 ¡ãC and then water (3 L) was added dropwise. The mixture was cooled to 25¡ãC and stirred for 5 hours and the resulting precipitate was collected by filtration, washed with water (300 mL x 2) and, dried under vacuum at 50¡ãC for 16 hours to afford 4,5-dibromo-2- methyl-2H-l,2,3-triazole (Intermediate 14e; 570 g, 60.8percent yield) as a solid. FontWeight=”Bold” FontSize=”10″ H NMR (400MHz, CDCb) delta 4.18 (s, 3H). 13C NMR (400MHz, CDCb) delta 124.25, 43.07.

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; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; FERON, James, Lyman; (80 pag.)WO2017/80980; (2017); 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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-(1,2,4-Triazol-1-yl)aniline

To a solution of formamidine from Step 4 (429mg, 1.045mmol) in acetic acid (3ml) was added the 4-triazolylaniline (184mg, 1.15mmol). The reaction was heated to 1250C for Ih. The mixture was cooled down basified with 15ml of 2N NaOH and the resulting precipitate isolated by filtration then dissolved in DCM and purified by column chromatography on silica with DCM / EtOH / NH3 400:8:1 up to 50:8:1 to give after concentration a cream solid (136mg, 25%). LC-MS rt 2.1 m/z 526 ES+.1H NMR (D6-DMSO) delta 10.06 (IH, broad s), 9.29 (IH, s), 8.82 (IH, s), 8.65 (IH, s) 8.21 (2H, m), 8.07 (2H, m), 7.83(4H, m), 7.69 (IH, d, J 10Hz), 7.32 (IH, dd, J 10Hz, 5Hz), 4.17 (2H, t, J 7.5Hz), 3.58 (4H, t, J 2.5Hz), 3.34 (2H, m, obscured by H2O), 2.40 (4H, t, J 2.5Hz), 1.92 (2H, t, J 7.5Hz).

The synthetic route of 6523-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); 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. 942060-54-0, name is 4-Bromo-2,5-dimethyl-2H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromo-2,5-dimethyl-2H-1,2,3-triazole

A solution of 4-bromo-2,5-dimethyl-triazole (107 mg, 0.611 mmol), 4-[7-tert-butyl-5-(4- chloro-3-fluoro-phenyl)furo[3,2-b]pyridine-2-carbonyl]-3,3-dimethyl-piperazin-2-one (200 mg, 0.4368 mmol) (Intermediate I) and K3P04 (185 mg, 0.873 mmol) in DMF (2.2 mL) is charged in a sealed 4 mL vial, flushed with nitrogen, added iodocopper (87.3 mg, 0.459 mmol) and N,N’-dimethylethane-1,2-diamine (46 mg, 55 iL, 0.524 mmol), and is flushed once more with nitrogen. The reaction is stirred at 100 C for three hours. The mixture is then filtered and purified using reverse phase prep. HPLC to afford 4-[7-tert-butyl-5-(4-chloro-3-fluoro- phenyl)furo[3,2-b]pyridine-2-carbonyl]-1-(2,5-dimethyltriazol-4-yl)-3,3-dimethyl-piperazin-2-one (110 mg, 45%). 1H NMR (400 MHz, DMSO-d6) 6 8.15 (dd, J = 11.0, 2.1 Hz, 1H), 8.07 – 7.97 (m, 1H), 7.82 (s, 1H), 7.72 – 7.66 (m, 1H), 7.63 (s, 1H), 4.02 (s, 5H), 3.92 (d, J = 5.2 Hz, 2H), 2.04 (s, 3H), 1.80 (s, 6H), 1.50 (s, 9H). ESI-MS m/z calc. 552.2052, found 554.64 (M+1)+; Retention time:4.29 minutes, Method J.

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 942060-54-0.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LIU, Bingcan; DORICH, Stephane; DE LESELEUC, Mylene; DUPONT-GAUDET, Kristina; JAMES, Clint, Alwyn; VAILLANCOURT, Louis; BEAULIEU, Marc-Andre; STURINO, Claudio; (236 pag.)WO2018/57588; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics