Triazoles

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

7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

2,3-Dichloro-5-nitropyridine (2 g, 10.36 mmol), 3-methyl-1H-1,2,4-triazole (1.722 g, 20.73 mmol) and Cs2CO3 (6.798 g, 20.73 mmol) were added to DMF (30 mL) and the reaction was stirred at rt for 12 h. The reaction mixture was quenched with water (200 mL). The mixture was extracted with ethyl acetate (100 mL*3). The organic layer was dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The crude residue was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100:0 to 50:50) to afford a mixture of compounds 20a and 20a-1 (780 mg, 31%) as a white solid. A mixture of 3-chloro-2-(3-methyl-i H-i ,2,4-tri-azol- i -yl)-5-nitropyridine, 20a and 3-chloro-2-(5-methyl-i H-i ,2,4-triazol-i -yl)-5-nitropyridine, 20a- i (780 mg, i .63mmol) was dissolved in MeOH (20 mE), and Zn (0) (i.058g, i 6.28 mmol) and aqueous NH4C1 (20 mE) were added.The reaction mixture was stirred at rt for i 6 h. The reactionmixture was filtered though a pad of diatomaceous earth andthe pad washed with ethyl acetate (20 mEx3). Water (50 mE)was added and the organic layer was separated, dried overNa2SO4, filtered and the filtrate was concentrated to drynessto give a crude mixture of compounds 20b and 20b- i (400mg, 59%) as a yellow solid. ?H NMR (400 MHz, METHANOE-d 4) oe ppm 2.43 (s, 3H), 2.85 (d, J=0.66 Hz, iH), 2.99(s, iH), 7.2i-7.23 (m, iH), 7.82 (d, J=2.65 Hz, iH), 7.86(dd, J=4.85, 2.43 Hz, iH), 8.02 (s, iH), 8.6i-8.65 (m, iH),8.63 (s, iH).

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

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

7343-34-2, A common compound: 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

4-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine (Intermediate 2) 4,6-dichloro-2-methylpyrimidine(2-1) (137.8 g, 845 mmol), 3,5-dimethyl-1H-1,2,4-triazole (2-2)[0080] (82 g, 845 mmol), and Cs2CO3 (275 g, 845 mmol) were suspended in DMF (1L) and the resulting mixture wasstirred at room temperature for 66 h. The mixture was then poured into water (2L) and stirred for 1 hour. The precipitatewas filtered, washed with water (2x) and dried under vacuum to afford Intermediate 2 as an off-white solid (130 g, 69percent).MS: m/z = 224.2 (M+H).

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, 3,5-Dimethyl-4H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; COX, Christopher, D.; BESHORE, Douglas, C.; KIM, June, J.; KUDUK, Scott, D.; McVEAN, Carol; REGER, Thomas; STEEN, Justin, T.; (54 pag.)EP2763672; (2016); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 288-36-8, name is 1H-1,2,3-Triazole, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 288-36-8

Step 1) Synthesis of 5-methyl-2- (2H-1, 2, 3-triazol-2-yl) benzoic acid To a solution of N, N-dimethylformamide (30 mL) were added sequentially 2H-1, 2, 3-triazole (3.45 g, 50 mmol) , 2-iodo-5-methyl benzoic acid (5.24 g, 20 mmol) , cesium carbonate (11.72 g, 36 mmol) , trans-N, N’-dimethyl-1, 2-cyclohexanediamine (0.51 g, 3.6 mmol) and cuprous iodide (0.38 g, 2 mmol) . The reaction was heated to 100 ? under N2. After reaction for 4 hours, the reaction mixture was cooled to rt, diluted with water (60 mL) and extracted with ethyl acetate (200 mL ¡Á 2) . The aqueous layer was acidified to pH 1 to 2 with concentrated hydrochloric acid, and then extracted with ethyl acetate (200 mL ¡Á 2) . The combined organic layers were dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/methanol (v/v) =50/1) to give the title compound as a yellow solid (2.76 g, 68 %) .MS (ESI, neg. ion) m/z: 202.1 [M-H] -;1H NMR (CD3OD, 600 MHz) d (ppm) : 7.88 (s, 2H) , 7.66 (d, 1H) , 7.59 (d, J= 8.2 Hz, 1H) , 7.50-7.48 (dd, J = 8.1 Hz, 1.1 Hz, 1H) , 2.45 (s, 3H) ; and13C NMR (CD3OD, 151 MHz) d (ppm) : 169.8, 140.7, 137.5, 136.7, 133.5, 131.5, 129.3, 126.0, 21.0.

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, 288-36-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (90 pag.)WO2017/88759; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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 4928-87-4 as follows. 4928-87-4

General procedure: To a 0.2 M solution of amine (0.1-10 mmol, 1 equiv) and carboxylic acid (1 equiv) in DCM was added Cl-HOBt (1.05 equiv)and Et3N (1.3 equiv) followed by EDC-HCl (1.2 equiv). The mixture was stirred at rt for 12 h. The crude mixture was diluted with DCM and washed once with 1 M HCl, once with satd NaHCO3 and once with brine. The DCM solution was evaporated to afford the product with >90% purity. The product was recrystallized from Et2O/hexane or purified by silica gel chromatography if necessary. Yields were typically >75%.

According to the analysis of related databases, 4928-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bremer, Paul T.; Hixon, Mark S.; Janda, Kim D.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3971 – 3981;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, name is 1-Methyl-1H-1,2,3-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. 16681-65-5

Example 65a: (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol A. solution of -BuLi (2.5 M in hexanes, 1.5 mL, 3.75 mmol) was added dropwise by syringe to a solution of 1 -methyl- 1H- 1 ,2,3-triazole (324 mg, 3.90 mmol) in dry THF (20 mL) in a dry ice- methanol bath. The suspension was stirred for 30 minutes, slowly allowing the reaction mixture to warm to -20 C. (4-CWoro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(l ,2-dimethyl-lH- imidaz.ol-5-yl)methanone (0.800 g, 1.89 mmol, Intermediate 46: step b) in dry THF (10 ml.) was added to the mixture via syringe and the resulting mixture was allowed to warm to ambient temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride. Water was added and the aqueous mixture was extracted with dichloromethane. The combined organic layers were dried (Na2S04), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM) to provide the title compound, NMR (400 MHz, CDCk) 5 8.24 (d, ./ = 1.9 Hz, i l l). 8.05 (s, 1H), 7.71 (d, ./ = 8.7 Hz, 1H), 7.37 (dd, J = 8.7, 2.0 Hz, 1H), 7.26 – 7.21 (m, 2H), 7.02 (s, 1H), 6.97 – 6.90 (m, 21 1). 5.95 (s, 1H), 4.16 (s, 2H), 4.07 (s, 3H), 3.87 (s, 3H), 3.31 (s, 3H), 2.09 (s, 3H); MS m/e 506.9 i M I .Example 65s was purified by chiral SFC (ChiralPai AD-H, 75:25 C02:MeOH + 0.3% ?PrNH2) to provide two pure enantiomers. The first eluting enantiorner was Example 65b: NMR. (400 MHz, CDC13) 6 8.23 – 8.19 (d, J = 2.1 Hz, 1H), 7.73 – 7.68 (d, J = 8.7 Hz, 1H), 7.39 – 7.33 (dd, J = 8.8, 2.2 Hz, 1 H), 7.29 – 7.23 (m, 2H), 7.07 (s, 1H), 6.98 – 6.91 (m, 2H), 6.47 (br s, 1 H), 6.03 (s, H I). 4.21 (s, 2H), 4.07 (s, 3H), 3.89 (s, M l ). 3.34 (s, 3H), 2.20 (s, 3H); MS m/e 506.2 [M]+. The second eluting enantiorner was Example 65c: 1H NMR (400 MHz, CDCI3) delta 8.19 (d, J = 2.1 Hz, 1H), 7.72 (d, J = 8.7 Hz, 1 H), 7.36 (dd, J = 8.7, 2.2 Hz, 1H), 7.29 – 7.24 (m, 2H), 7.1 1 (s, 1H), 6.97 – 6.91 (m, 2H), 6.06 (s. I I I). 4.23 (s, 2H), 4.08 (s, 3H), 3.90 (s, 3H), 3.36 (s, 3H), 2.24 (s, 3H); MS m/e 506.2 [M]”

Statistics shows that 16681-65-5 is playing an increasingly important role. we look forward to future research findings about 1-Methyl-1H-1,2,3-triazole.

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; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics