Day: November 2, 2020

7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-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.

4-chloro-8-methoxy-2- methylquinoline (100 mg, 0.481 mmol) was reacted with 3-methyl- IH-l, 2,¡¤ 4-triazole (46.0, 0.554 mmol) according to the synthesis of 4-(4-fluoro- 1 /Y-pyrazol- 1 -yl)-8-mcthoxy-2-mcthylquinolinc to give a mixture of the title compounds. MS (m/z): 255.3 [M+H+] Step B Synthesis of 2-methyl-4-(3-methyl-l//-l,2,4-triazol-l-yl)quinolin-8-ol and 2-methyl- 4-(5-methyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-ol (0284) A mixture of 8-mcthoxy-2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolinc and 8- mcthoxy-2-mcthyl-4-(3-mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolinc (153 mg, 0.602 mmol) was demethylated according to the synthesis of 4-(4-fluoro-l//-pyrazol-l-yl)-2-methylquinolin-8-ol to give a mixture of the title compounds. MS (m/z): 241.1 [M+H+]

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 7170-01-6.

Reference:
Patent; PHARVARIS B.V.; GIBSON, Christoph; SAUPE, Joern; AMBROSI, Horst-Dieter; HAUSTEDT, Lars Ole; (99 pag.)WO2019/101906; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Example 1-30 Preparation of provided 5-(5-((1R, 3s, 5S)-8-(4H-1,2, 4-triazole-3-carbonyl)-8- azabicyclo[3.2.1 ]octan-3-yl)-6-acetyl-7-aminopyrazolo[1,5-a]pyrimidin-3-yl)picolinic acidA mixture of methyl 5-(6-acetyl-7-amino-5-((1 R,3s,5S)-8- azabicyclo[3.2.1]octan-3-yl)pyrazolo[1 ,5-a]pyrimidin-3-yl)picolinate (99.5 mg, 0.237 mmol), 4H-1 ,2,4-triazole-3-carboxylic acid (32.2 mg, 0.285 mmoL), EDC (90.7 mg, 0.475 mmol), HOBt (64.1 mg, 0.475 mmol) and DIEA (247.6 ul, 1.42 mmol) in DMF (5 mL) was stirred at room temperature for 1 h. Concentration provided crude methyl 5-(5-((1 R,3s,5S)-8-(4H-1 ,2,4-triazole-3-carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)-6- acetyl-7-aminopyrazolo[1 ,5-a]pyrimidin-3-yl)picolinate. MeOH (2 ml), THF (1 ml) and 1 N NaOH (2 ml) were added and the mixture was stirred at 50C until LCMS indicated complete conversion. Concentration and Purification with prep-LC provided5- (5-((1 R,3s,5S)-8-(4H-1 ,2,4-triazole-3-carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)-6- acetyl-7-aminopyrazolo[1 ,5-a]pyrimidin-3-yl)picolinic acid, LCMS tR = 1.85 Min (10 min run, UV254nm). Mass calculated for, M+ 501.1 , observed LC/MS m/z 501.96 (M+H).

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; MERCK SHARP & DOHME CORP.; SCHERING CORPORATION; SIDDIQUI, M. Arshad; NAN, Yang; PATEL, Mehul, F.; REDDY, Panduranga Adulla P.; MANSOOR, Umar Faruk; MENG, Zhaoyang; VITHARANA, Lalanthi Dilrukshi; ZHAO, Lianyun; MANDAL, Amit, K.; LIU, Duan; TANG, Shuyi; MCRINER, Andrew; BELANGER, David, B.; CURRAN, Patrick, J.; DAI, Chaoyang; ANGELES, Angie, R.; YANG, Liping; DANIELS, Matthew Hersh; WO2011/90935; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

956317-36-5, A common compound: 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, 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.

General procedure: A mixture of the primary amine, 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid 31 (0.33 g, 1.6 mmol), N,N-diisopropylethylamine(DIPEA, 2.5 mL, 14.7 mmol), and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate(HATU, 0.91 g, 2.4 mmol) in DMF (3.2 mL) was stirredat room temperature for 17 h. The reaction was quenched by theaddition of water, and the mixture was extracted with EtOAc.The organic layer was washed with brine, dried over Na2SO4, filtered,and concentrated under reduced pressure. The resulting residuewas purified by preparative HPLC to obtain the title compound7a as a colorless solid (0.18 g, 28% over 2 steps).

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, 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Futamura, Aya; Nozawa, Dai; Araki, Yuko; Tamura, Yunoshin; Tokura, Seiken; Kawamoto, Hiroshi; Tokumaru, Yuichi; Kakihara, Sora; Aoki, Takeshi; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5203 – 5215;,
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. 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, A new synthetic method of this compound is introduced below., 7343-34-2

A solution of 1.94 g (20 mmol) of 3,5-dimethyl-1,2,4-triazole was mixed with 19.4 ml of tetrahydrofuran, and 2.29 g (10 mmol) of pure 2-bromoisobutyryl bromide was added dropwise for about 30 minutes, stirring was continued for 2 hours. The insoluble material was filtered off and the filtrate was concentrated to dryness under reduced pressure. 5 ml of methyl tert-butyl ether was added, stirred for 30 minutes, filtered, and the cake was dried to obtain 2.12g of product, yield 86percent.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Ningbo Baisijia Pharmaceutical Technology Co., Ltd.; Jin Chunhua; Tang Jianbo; Wang Kedi; Zhu Qinfeng; (13 pag.)CN106866558; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-33-1, The chemical industry reduces the impact on the environment during synthesis 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

To a 250 mL reaction flask was added 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100¡ã C. for 20 hours (h). The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite?. The Celite? was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography using EtOAc/hexanes as eluent to yield the title compound (3.78 g, 73percent): mp 69-70¡ã C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta ?58.04; EIMS m/z 307 ([M]+).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; WHITEKER, Gregory T.; US2014/275560; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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. 16681-65-5

A solution of n-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-Chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-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 (Na2SO4), 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. 1H NMR (400 MHz, CDCl3) delta 8.24 (d, J=1.9 Hz, 1H), 8.05 (s, 1H), 7.71 (d, J=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, 2H), 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 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-65-5, its application will become more common.

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

956317-36-5, Adding some certain compound to certain chemical reactions, such as: 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, 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 956317-36-5.

TEA (1.20 mL, 8.63 mmol) was added to a solution of N-ethyl-2[3-(5-fluoro-pyridin-2-yl)-1H-pyrazol-l-yl] ethanamine dihydrochloride(0.50 g, 1.63 mmol) in CHC13 (5 mL) at room temperature.5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (0.36 g, 1.79 mmol)and propylphosphonic acid anhydride (cyclic trimer) (50% solutionin DMF [approximately 1.6 mol/L], 1.32 mL, 2.12 mmol) wereadded to the reaction solution under cooling in ice water. Theresultant mixture was stirred at 50 C for 5 h. After standing untilcooled to room temperature, water was added thereto, followedby extraction with CHCl3. The organic layer was washed with brine.Then, the organic layer was dried over MgSO4 and the desiccantwas filtered off. Then, the solvent was distilled off under reducedpressure. The obtained residue was purified by column chromatography(20-80% EtOAc in hexanes) and washed with Et2O to yieldthe title compound 4a as a colorless powder (0.51 g, 75%).

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 956317-36-5.

Reference:
Article; Suzuki, Ryo; Nozawa, Dai; Futamura, Aya; Nishikawa-Shimono, Rie; Abe, Masahito; Hattori, Nobutaka; Ohta, Hiroshi; Araki, Yuko; Kambe, Daiji; Ohmichi, Mari; Tokura, Seiken; Aoki, Takeshi; Ohtake, Norikazu; Kawamoto, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1260 – 1275;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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. 288-36-8

To a mixture ofthe product from step 2 (7.9 g, 38 mmol), cesium carbonate(24.830 g,76 mmol) and Cui (2.88 g, 7.6 mmol) in DMF (200 mL) were added 2H-[1,2,3]triazole (5.24g,76 mmol) and N,N’-dimethyl-cyclohexane-1,2-diamine (0.9 g, 6.5 mmol) and the mixture washeated to 110 C overnight. The cooled reaction mixture was adjusted to ~pH 12 with 1Msodium hydroxide and extracted with EtOAc (50 mL x 3). The aqueous layer was adjusted to~pH 4 with 1M HCl and extracted with EtOAc (50 mLx4). The extracts was dried over Na2S04,35 filtered, the filtrate concentrated in vacuo and the residue purified by chromatography on silica (Petroleum ether: EtOAc =10:1) to provide the title compound (4.1 g). LRMS m/z (M+H)196.0 found, 196.0 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/18029; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-88-5, A common heterocyclic compound, 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, 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.

Step 1 Preparation of 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester A solution of 1H-[1,2,4]triazole-3-carboxylic acid methyl ester (3.0 g, 0.023 mol) in N,N-dimethylformamide at 25¡ã C. was treated with triphenylmethylchloride (7.2 g, 0.025 mol) and triethylamine (6.41 mL, 0.046 mol). The reaction was stirred at 25¡ã C. for 4 days. At this time, the reaction was concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with a dilute 1N aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solids were diluted with ether, collected by filtration, washed with ether, and dried in vacuo to afford 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester (2.45 g, 84percent) as a white solid: LR-FAB for C23H19N3O2 (M+H)+ at m/z=370.

The synthetic route of 4928-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dunten, Peter W.; Foley, Louise H.; Huby, Nicholas J.S.; Pietranico-Cole, Sherrie L.; Yun, Weiya; US2004/14766; (2004); 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 288-36-8 as follows. 288-36-8

Intermediate 3: 5-Methyl-2-(2H-l,2,3-triazol-2-yl)benzoic acid To the solution of 1,2,3-triazole (1.99 g, 28.93 mmol) in DMF (7.0 ml) at 0-10UC was added cesium carbonate (4.7 g, 14.45 mmol), N,N-dimethylethylenediamine (0.127 g, 1.45 mmol), copper(I) iodide (0.068 g, 0.36 mmol) and 2-iodo-5-methylbenzoic acid (3.79 g, 14.46 mmol). The reaction was subjected to microwave irradiation at 125 C for 15 minutes, and then poured into water (20 ml) and extracted with ethyl acetate. The combined organics were washed with brine, dried (sodium sulphate) and concentrated in vacuo. The crude product was purified by column chromatography (0-3 % methanol in dichloromethane) to afford the title compound.1H NMR (DMSO-i/6) delta ppm 2.42 (s, 3 Eta), 7.49 – 7.52 (m, 1 Eta), 7.58 – 7.64 (m, 2 Eta), 8.05 (s, 2 H), 13.01 (s, 1 H)MS ES+: 204

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; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics