Category: Triazoles

Synthetic Route of 27808-16-8, 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. 27808-16-8 name is 4-Methyl-1H-1,2,3-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.

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. Zn (1491.96 mg, 22.95 mmol) was added to a solution of mixture of 3-chloro-2-(4-methyl-2H-i,2,3-tri- azol-2-yl)-5-nitropyridine and 3-chloro-2-(4-methyl-i H-i, 2,3-triazol-i-yl)-5-nitropyridine, i25a (1.1 g, 2.30 mmol) in aqNH4C1 (30 mE) and H20 (30 mE). The mixture was stirred at it for 16 h. To the suspension was added aq NaHCO3 to adjust to pH 9-10, and the mixture was filtered through a pad of diatomaceous earth. The filter cake was washed with CH2C12 (100 mEx3). The combined filtrates were washed with brine (200 mE), dried over MgSO4 and concentrated under reduced pressure to afford mixture of 5-chloro-6-(4-methyl-2H- 1 ,2,3-triazol-2-yl)pyridin-3-amine and 5-chloro-6-(4-methyl-i H-i ,2,3-triazol- 1 -yl)pyriF din-3-amine, 125b (1 g) as a brown solid, used directly for the next step. LCMS (ESI) mlz M+H: 209.7

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

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

Electric Literature 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.

3A: (2S,4R)-5-(3′-Fluorobiphenyl-4-O-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid 1,2,3-Triazole-4-carboxylic acid (27.3 mg, 241 mumol) was combined with EDC (42.7 muL, 241 mumol), 4-methylmorpholine (1 eq.) and HOBt (32.6 mg, 241 mumol) in DMF (0.2 mL). The resulting mixture was stirred for 5 minutes at room temperature. A solution (2S,4R)-4-amino-5-(3′-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-methylpentanoic acid (80 mg, 240 mumol) and 4-methylmorpholine (53.1 muL, 483 mumol) in DMF (0.3 mL) was added, and the resulting mixture was stirred for 15 minutes. The reaction was quenched with ACOH and the product was purified by preparative HPLC and lyophilized to yield the title compound (30 mg). MS m/z [M+H]+ calc’d for C22H23FN4O4, 427.17. found 427.2.

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; Fleury, Melissa; Hughes, Adam D.; US2014/45906; (2014); 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. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: A mixture of dimedone (1 mmol), aldehyde or isatin (1 mmol) and 4-phenylurazole (1 mmol), and catalyst (0.01 g, 5 mol%) in water (5 mL) was refluxed. After completion of the reaction that was monitored by TLC (EtOAc:n-hexane, 1:3), the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with water and cooled with ethanol to afford the pure product.

According to the analysis of related databases, 15988-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Seyyedhamzeh, Mozhdeh; Shaabani, Shabnam; Hamidzad Sangachin, Mona; Shaabani, Ahmad; Research on Chemical Intermediates; vol. 42; 4; (2016); p. 2845 – 2855;,
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

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

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

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

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

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 10570-40-8, name is 4-Methyl-4H-1,2,4-triazole, A new synthetic method of this compound is introduced below., category: Triazoles

4.2 1-(4-Methyl-4H-1,2,4-triazol-3-yl)octan-1-ol To a solution of 4-methyl-1,2,4-triazole (681 mg, 7.78 mmol), TMEDA (0.40 ml) in dry THF (10 ml) and at -60 C, 2.69 M n-BuLi solution (2.9 ml, 7.80 mmol) was added drop wise. After stirring at -60 C for 30 min, 10 ml of dry THF solution of octanol (1.30 mL, 8.33 mmol) was added and the mixture was stirred for additional 4 h at -60 C to -30 C. Then H2O was added and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1-5% methanol/chloroform) as a colorless solid (1.13 g, 69%): Mp. 63-65 C; 1H NMR (500 MHz, CDCl3) delta 0.87 (3H, t, J = 6.6 Hz), 1.30-1.26 (9H, m), 1.46 (1H, q, J = 5.2 Hz), 1.93-1.84 (2H, m), 3.50 (1H, br s), 3.93 (3H, s), 4.82 (1H, q, J = 6.3 Hz), 7.76 (1H, s); 1H NMR (300 MHz, DMSO) delta 0.88 (3H, t, J = 6.9 Hz), 1.26-1.49 (14H, m), 1.87-1.93 (2H, m), 2.70 (1H, d, J = 7.5 Hz) 3.92 (3H, s), 4.84 (1H, q, J = 6.9 Hz), 7.79 (1H, s); 13C NMR (126 MHz) delta 14.1, 22.7, 25.2, 29.5, 31.9, 33.7, 35.4, 39.8, 64,2, 143.6, 155.0; HRMS (ESI) m/z calcd for C11H21N3NaO (M + Na)+ 234.1582, found. 234.1573.

The synthetic route of 10570-40-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Suzuki, Yumiko; Iwata, Naoto; Dobashi, Kohei; Takashima, Ryo; Arulmozhiraja, Sundaram; Ishitsubo, Erika; Matsuo, Naoya; Tokiwa, Hiroaki; Tetrahedron; vol. 74; 3; (2018); p. 392 – 400;,
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. 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. Product Details of 16681-70-2

[0758] 3H-1,2,3-triazole-5-carboxylic acid (2.5 mg, 22f.tmol) was combined with HATU (8.4 mg, 22 flillOl) in DMF(0.3 mL) and stirred for 10 minutes; Et3N (1 eq.) was addedand the mixture was stirred for 1 minute. Compound 2 (22f.tmol) was dissolved in DMF (0.5 mL) and Et3N (3.1 f.LL, 22f.tmol) was added, followed by addition of the activated acidsolution. The mixture was stirred for 30 minutes and concentratedto yieldCompound3, which was carried to the next stepwithout purification.

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

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