Day: April 27, 2021

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. 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., category: Triazoles

4,5-dibromo-2-methyl-2H-l,2,3-triazole. Iodomethane (19.0 g, 133.8 mmol) was added to a solution of 4,5-dibromo-2H-l,2,3-triazole (15.0 g, 66.7 mmol) and potassium carbonate (18.1 g, 131.2 mmol) in N,N-dimethylformamide (100 mL) at -10C. The mixture was warmed to room temperature and stirred for 12 hours. The reaction mixture was concentrated to give a residue. The residue was dissolved in ethyl acetate (200 mL), washed by brine (50 mL x 3), dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by column chramtography (silica gel, dichloromethane/methanol = 15 : 1) to afford 4,5-dibromo-2-methyl-2H-l,2,3-triazole as a white solid (5.9, 36.9 %).

According to the analysis of related databases, 22300-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. name: Sodium 1,2,4-triazol-1-ide

Production Example 3Synthesis of 5-(4-chlorobenzyl)-2-meth- oxymethoxymethyl-2-methyl- 1 -(1H- 1 ,2,4-triazole- 1-ylmethyl)cyclopentanol (Compound (4)): 10182] 1H-i,2,4-triazolesodium salt (13.1 mmol) was dissolved in NMP (7 ml), and then heated to an internal temperature of 115 C. To this, Compound (6) (8.76 mmol) was added, and the mixture was thoroughly washed with NMP (1.8 ml). After the internal temperature was returned to 115 C., sodium t-butoxide (5.26 mmol) and trimethyl sulfoxonium bromide (1.476 mmol) were gradually added to the mixture over a period of 3 hours. After the addition, the resulting mixture was stirred at a temperature of 115 C. for 75 minutes. After the reaction solution was cooled down to35 C., water was added to the reaction solution, and then extraction with ethyl acetate was performed. An organic layer of the extract was washed with water and saturated brine, and then dried with anhydrous sodium sulfate. The solvent was distilled off, followed by purification of the residue by silica gel column chromatography, and thus Compound (4), which was a mixture of isomers, was obtained.10183] Yield: 71%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41253-21-8, its application will become more common.

Reference:
Patent; KUREHA CORPORATION; Miyake, Taiji; Araki, Nobuyuki; Yamazaki, Toru; US2014/94362; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1001401-62-2, The chemical industry reduces the impact on the environment during synthesis 1001401-62-2, name is 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: TBTU (1.1 mmol) was added to a solution of the required carboxylic acid A-1 (1.0 mmol) and DIPEA (2.0 mmol) in DMF (2.0 mL). After stirring at rt for 10 min a solution of the required amine B-3 (1 .0 mmol) in DMF (1.0 mL) was added. The resulting rxn mixture was stirred at rt for up to 3 d before being purified directly by prep. HPLC (method G) to furnish the desired 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, 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi T.; WO2014/57435; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2,Some common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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.

Compound 3 (30 mg, 199 muiotaetaomicron) was combined with 3H-[l,2,3]triazole-4- carboxylic acid (22 mg, 199 muiotaetaomicron), HATU (76 mg, 199 muiotaetaomicron) and DIPEA (104 mu, 596 muiotaetaomicron) in DMF (1 mL) and stirred at room temperature for 20 minutes then concentrated in vacuo and the crude residue was purified by normal phase chromatography (0-100% EtOAc/hexanes). The intermediate (30 mg, 67 muiotaetaomicron) was dissolved in THF (1 mL) and 10N NaOH (268 mu^, 268 muiotaetaomicron) and stirred at room temperature for 1 hour. The mixture was acidified with AcOH and purified by preparative HPLC to yield Compound 4 (10 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-[1,2,3]Triazole-4-carboxylic acid, its application will become more common.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 67545-00-0, 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. 67545-00-0, name is 4-Amino-1-methyl-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 293c 5-Bromo-1-methyl-3-(1-methyl-1H-1,2,3-triazol-4-ylamino)pyridin-2(1H)-one 293c Following the procedure in Example 130c, and starting with 293b (500 mg, 5.10 mmol, 1.0 eq.) and 3,5-dibromo-1-methylpyridin-2(1H)-one (2.04 g, 7.65 mmol, 1.5 eq.) afforded 293c as a yellow solid (760 mg, 52%). MS-ESI: [M+H]+ 283.9.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-1-methyl-1,2,3-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1455-77-2, 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. 1455-77-2 name is 3,5-Diamino-1,2,4-triazole, 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.

Added to three neck fever bottle 126mmol oleic acid, 60mmol3,5-diamino -1, 2, 4-three nitrogen […] 20.9g glycol solvent, under the protection of argon gas, heating 80 ¡ãC after melting, by adding 3mmol potassium hydroxide, wherein the oleic acid: 3,5-diamino -1, 2, 4-triazole: potassium hydroxide mole ratio is 2.1: 1 : 0.05, glycol as the above-mentioned reactant of the total weight of the 50percent. Continued heating to 150 ¡ãC, reaction 12h rear, with 1percent sodium carbonate water solution, in order to remove unreacted oleic acid and the solvent is ethylene glycol, yellow solid is obtained after drying a heterocycle-containing fatty acid amide-based intermediate A.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Diamino-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; China Petroleum & Chemical Corporation; Yu, Jianye; Lu, Minhui; Yuan, Ping; Yuan, Yufeng; (9 pag.)CN105693640; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1257633-67-2, These common heterocyclic compound, 1257633-67-2, name is 1-(tert-Butyl)-4-(diethoxymethyl)-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.

Synthesis of 1-tert-butyl-1H-1,2,3-triazole-4-carbaldehyde To a 50-mL round bottom flask was added a solution of 1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole (1.28 g, 5.63 mmol) in dichloromethane (6.0 mL), followed by addition of water (3.0 mL) and trifluoroacetic acid (1.0 mL). The reaction was stirred vigorously under nitrogen for 3 h until TLC analysis indicated the complete disappearance of the starting material (10% EtOAc in dichloromethane, starting material Rf 0.5, product Rf 0.6, KMnO4 stain). The reaction mixture was diluted with EtOAc (100 mL), washed with sat aq NaHCO3 (3*40 mL) and brine (40 mL). The combined organic phases were dried over anhydrous MgSO4, filtered, and concd in vacuo to provide 0.71 g of a light yellow oil (yield: 82%). The crude product was used without purification.

Statistics shows that 1-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 1257633-67-2.

Reference:
Patent; Albert Einstein College of Medicine of Yeshiva Uni; Wu, Peng; Soriano del Amo, David; Wang, Wei; Marlow, Florence L.; US2013/295019; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 143426-50-0, name is 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, 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 143426-50-0, COA of Formula: C9H9N3O

A mixture of 14 (100 mg, 0.34 mmol), [4-(1H-1,2,4-triazol-1-yl)phenyl]methanol16 (118 mg, 0.67 mmol)and (tributylphosphoranylidene)acetonitrile (163 mg, 0.68 mmol) in toluene (2 mL) wasstirred at 100 C for 1.5 h and allowed to cool to room temperature. Themixture was evaporated in vacuo and the crude mixture was purifiedusing amino-functionalized silica-gel column chromatography (CHCl3)and washed with diisopropyl ether to give N-ethyl-5-(2-methyl-8-{[4-(1H-1,2,4-triazol-1-yl)phenyl]methoxy}imidazo[1,2-a]pyridin-3-yl)pyridine-2-carboxamide (87 mg). Next, 4M HCl in EtOAc (0.20 mL,0.80 mmol) was added to a 2.2 mL EtOAc-EtOH (10:1) solution of thiscompound. After stirring at room temperature, the precipitate was filteredto give the product as a beige solid (87 mg, 49% yield [2 steps]).1H NMR (DMSO-d6) delta ppm 1.16 (3H, t, J=7.1 Hz), 2.50 (3H, s),3.33-3.43 (2H, m), 5.59 (2H, s), 7.39 (1H, dd, J=8.0, 6.9 Hz), 7.63(1H, d, J=8.2 Hz), 7.80-7.85 (2H, m), 7.94-7.99 (2H, m), 8.24-8.32(4H, m), 8.88 (1H, dd, J=2.0, 1.0 Hz), 8.96 (1H, t, J=6.1 Hz), 9.37(1H, s); MS (ESI) m/z [M+H]+ 454. HRMS (ESI) m/z calcd forC25H24N7O2 ([M+H]+): 454.1986. Found: 454.1989. Anal. calcd forC25H23N7O21.5HCl¡¤2.3H2O0.15EtOAc: C, 54.63; H, 5.43; N, 17.42;Cl, 9.45. Found: C, 54.87; H, 5.32; N, 17.72; Cl, 9.10.

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

Reference:
Article; Sekioka, Ryuichi; Honda, Shugo; Honjo, Eriko; Suzuki, Takayuki; Akashiba, Hiroki; Mitani, Yasuyuki; Yamasaki, Shingo; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference 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.

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’-dimethylcyclohexane-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 room temperature, 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 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-2, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. A solution of the acid (3.56 g, 17.52 mmol) in 150 mL of DCM was stirred and cooled to 00C. The solution was treated with oxalyl chloride (1.9 mL, 21.9 mmol) and DMF (68 muL, .878 mmol). The solution was slowly warmed to room temperature and stirred overnight. Solvent was concentrated and the resulting solid was azetroped with DCM and concentrated to provide A-4 as a yellow solid.

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; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; FLORES, Broc; SCHREIER, John, D.; WO2010/48016; (2010); 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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C2H3N3

To a solution of 5-fluoro-2-iodo- benzoic acid (3.86 g, 14.65 mmol), 2H-[1 ,2,3]triazole (2.5 g, 36.2 mmol),Cs2CO3 (8.62 g, 24.5 mmol), trans-N, N’-dimethyl-cyclohexane-1 ,2-diamine (0.4 ml_), Cul (244 mg) and DMF (13 ml_) were added to a microwave ready vessel and heated to 100 C for 10 min. The mixture was cooled, diluted with water, and extracted with EtOAc. The aqueous layer was acidified and extracted with EtOAc. The organic layer was dried over Na2SO and concentrated. The residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1 %HOAc/DCM) gave the product as a white powder, (2.14 g, 71 %). 1H NMR (400 MHz, CD3OD): 7.91 (s, 2H), 7.76 (dd, J = 8.9, 4.8 Hz, 1 H), 7.59 (dd, J = 8.5, 2.9 Hz, 1 H), 7.49 – 7.42 (m, 1 H).; Intermediate 53: 2-[1 ,2,3]Triazol-1 -yl-benzoic acid.The title compound was isolated from the synthesis of Intermediate 13. 1H NMR (400 MHz, CD3OD): 6.70 (d, J = 0.9 Hz, 1 H), 6.50 (dd, J = 7.7, 1 .5 Hz, 1 H), 6.30 (d, J = 1 .0 Hz, 1 H), 6.24.6.18 (m, 1 H), 6.17 -6.1 1 (m, 1 H), 6.01 (dd, J = 7.8, 1 .0 Hz, 1 H).

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; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics