Category: Triazoles

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

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

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

Synthetic Route of 41253-21-8, 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 41253-21-8 as follows.

To a solution of 4-cyclohexyl-4-methansulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (39 g, 103.8 mmol) in N,N-dimethylformamide (200 mL) is added sodium triazole (38 g, 415.2 mmol). The resulting solution is heated to 100 C. for 24 hours then cooled to room temperature. The solvent is removed under reduce pressure and the crude product purified over silica (80:20 EtOAc:hexane) to afford 28.7 g (79.7% yield) of the desired compound as a colorless solid. 1H NMR (CD3OD) delta 0.95-1.90 (m, 15H), 1.46 (s, 9H), 3.45-3.55 (m, 4H), 4.34 (s, 2H), 7.99 (s, 1H), 8.48 (s, 1H). MS (ESI) m/z 349, (M+H+), 371(M+Na+)

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Procter & Gamble Company; US2003/236230; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 15294-81-2, These common heterocyclic compound, 15294-81-2, name is 4,5-Dibromo-1H-1,2,3-triazole, 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.

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 -10C under a nitrogen atmosphere and iodomethane (147.91 mL, 2.38 mol) was added dropwise. The reaction was then stirred at 25C 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 – 10C under a nitrogen atmosphere and iodomethane (131.48 mL, 2.11 mol) was added dropwise. The reaction was then stirred at 25C 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 C for 2 hours and the resulting precipitate filtered and dried under vacuum to afford undesired 4,5-dibromo-l-methyltriazole (220 g, 23.5%) 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 C and then water (3 L) was added dropwise. The mixture was cooled to 25C 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 50C for 16 hours to afford 4,5-dibromo-2- methyl-2H-l,2,3-triazole (Intermediate 14e; 570 g, 60.8% 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.

The synthetic route of 15294-81-2 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 288-36-8, 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 288-36-8 as follows.

The 1, 2, 3-triazole (3.45g, 50mmol), 2-iodo-5-methyl benzoic acid (5.24g, 20mmol), cesium carbonate (11.72g, 36mmol), trans-N, N ‘-dimethyl -1 , 2-cyclohexanediamine (0.51g, 3. 6mmol), cuprous iodide (0.38g, 2mmol) and N, N-dimethyl formamide (30 ml) are sequentially added to the 100 ml round bottom flask in a single port, the resulting reaction mixture under the protection of nitrogen is gradually heated up to 100 C, reaction 4 hours. Stop the reaction, cooling to room temperature to be reacted, water (150 ml) is diluted, and using ethyl acetate (200 ml ¡Á 2) extraction . Remove organic layer, the aqueous layer with concentrated hydrochloric acid (the mass fraction is 36.5%) acidified to pH to 1-2, then using ethyl acetate (200 ml ¡Á 2) extraction, and combined with the organic layer dried with anhydrous sodium sulfate. Filtering, the filtrate concentrated under reduced pressure, the resulting residue is purified by silica gel column chromatography (dichloromethane / methanol (v / v) = 50/1) to obtain the title compound as yellow solid (2.76g, 68%) .

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Jinchuan, Fei; Gao, Heng; Zhang, Ji; Zhang, Yingjun; (84 pag.)CN105461699; (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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 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.

According to the analysis of related databases, 61-82-5, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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 16681-70-2, Recommanded Product: 1H-[1,2,3]Triazole-4-carboxylic acid

[0839] lH-1,2,3-triazole-4-carboxylic acid (3.8 mg, 34f.tmol)was combined withHATU (12.9 mg, 34 flillOl) inDMF(2 mL) and stirred at room temperature for 15 minutes. Compound3 (13 mg, 31 f.tmol) and DIPEA (16 f.LL, 92 flillOl) werethen added. The solution was stirred at room temperature for15 minutes, at which time LCMS showed reaction completion. The solvent was removed in vacuo and the crude residuewas purified by reverse phase chromatography to yield Compoundb (15 mg) as a TFA salt. MS m/z [M+Ht calc’d forC25H29CIFN50 4 , 518.19. found 518.

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

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

Application of 49607-51-4, 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. 49607-51-4 name is 1-Methyl-1H-1,2,4-triazol-3-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.

Triphosgene (0.588 g, 1.982 mmol) was added to a stirred solution of (4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine (0.5 g, 1.982 mmol) in tetrahydrofuran (20 mL) at 0¡ã C. and stirred for 30 min. Triethylamine (0.829 mL, 5.94 mmol) and 1-methyl-1H-1,2,4-triazol-3-amine (0.486 g, 4.95 mmol) was added at 0¡ã C. The reaction mixture was stirred for 48 h at 70¡ã C. The reaction mixture was cooled to 28¡ã C., and was partitioned between water (50 mL) and DCM (50 mL). The separated organic layer was washed with water and brine. The organic layer was dried over anhydrous Na2SO4, filtered and filtrate was evaporated to afford crude yellow solid (TLC eluent: 10percent MeOH in EtOAc: Rf-0.3; UV active). The crude compound was purified by (100-200 mesh) silica gel and was eluting with 5percent MeOH in ethyl acetate to afford (4S)?N-(1-methyl-1H-1,2,4-triazol-3-yl)-7-(2-methylpyridin-4-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-car-boxamide (0.215 g, 0.563 mmol, 28.4percent yield) as light yellow solid, LCMS (m/z): 377.28 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 13.44 (s, 1H), 8.55 (d, J=5.2 Hz, 1H), 8.36 (s, 1H), 7.96 (s, 1H), 7.86-7.61 (m, 3H), 5.44 (dd, J=5.8, 3.0 Hz, 1H), 3.83 (s, 3H), 3.27 (d, J=30.5 Hz, 3H), 2.95 (dd, J=12.0, 3.2 Hz, 1H), 2.59 (s, 3H), 2.23 (ddt, J=16.9, 9.7, 4.4 Hz, 1H), 1.91 (dt, J=14.7, 7.4 Hz, 1H).

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

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 16681-65-5, The chemical industry reduces the impact on the environment during synthesis 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

1-Methyl-1H-1,2,3-triazole was prepared according to the literature reference WO2008/98104. To a 2 L flask containing 1-methyl-1H-1,2,3-triazole (9 g, 108.3 mmol) was added THF (1500 mL) and the solution was cooled to -40 C. To this colorless homogeneous solution was added n-butyllithium (2.5 M in hexanes, 45 mL, 112.5 mmol) dropwise which immediately afforded a dark brown viscous mixture. The mixture was kept between -10 to -20 C. for 60 minutes, then a THF solution of 2,4-dimethylthiazole-5-carbaldehyde (17.2 g, 121.8 mmol in 200 mL THF) was introduced via cannula. Once the aldehyde was added the reaction was allowed to warm to room temperature. After 3 hours, the reaction was quenched by pouring into a saturated solution of aqueous NH4Cl. The aqueous portion was extracted with EtOAc in portions, 7*400 mL. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a brown oil. Chromatography on silica gel (10% acetone-DCM increasing to 50% acetone and increasing to 10% MeOH-DCM) provided the title compound as an amber solid.

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

Reference:
Patent; Janssen Pharmaceutica NV; 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.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics