Triazoles

4928-88-5, These common heterocyclic compound, 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, 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.

A solution of [LH-[1,] 2,4] triazole-3-carboxylic acid methyl ester (3.0 g, 0.23 mol) in [N, N-DIMETHYLFORMAMIDE] (76 mL) at [25 oC] was treated with triphenylmethylchloride (7.2 g, 0.23 mol) and triethylamine (6.41 mL, 0.23 mol). The reaction mixture was stirred at [25 oC] for 4 days and then diluted with ethyl acetate. The mixture was then washed with a dilute aqueous hydrochloric acid solution. At this time, methanol was added to the organic layer. A precipitate formed and was removed by filtration. The organics were further washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was triturated with diethyl ether. The solid was collected by filtration and washed again with diethyl ether to afford 1-trityl-1H-[1, 2,4] triazole-3-carboxylic acid methyl ester as a white solid (2.45 g, 84percent) which was used without further purification.A solution of 2, 2-dimethyl-propionic acid 8- (4-acetylamino-benzyl)-3-butyl-2, 6- dioxo-1, 2,3, 6-tetrahydro-purin-7-ylmethyl ester (104 mg, 0.22 mmol) in acetonitrile (2.0 mL) was treated with [1,] 8-diazabicyclo [5.4. 0] [UNDEC-7-ENE] (0.03 mL, 0.24 mmol) and [2-BROMOMETHYL-1-FLUORO-4-NITRO-BENZENE] (56.6 mg, 0.24 mmol). The resulting solution was heated to [50 oC FOR] 6 h. At this time, another portion of 1,8- diazabicyclo [5. [4 : 0] UNDEC-7-ENE] (0.03 mL, 0.24 mmol) was added. The reaction was stirred at [25 oC] for 18 h. At this time, the reaction was poured into ethyl acetate (200 mL) and was washed with a 1N aqueous hydrochloric acid solution [(1] x 50 mL) and a saturated aqueous sodium chloride solution [(1] x 50 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60,230-400 mesh, 1: 1 ethyl acetate/petroleum ether) afforded 2,2- dimethyl-propionic acid 8- (4-acetylamino-benzyl)-3-butyl-1- (2-fluoro-5-nitro-benzyl)- 2, [6-DIOXO-1,] 2,3, 6-tetrahydro-purin-7-ylmethyl ester (45.3 mg, 33percent) as a tan solid

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 4928-88-5.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); 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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., 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.

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; 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

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. 288-88-0, name is 1H-1,2,4-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 288-88-0

Example 3. Synthesis of 1 -Ethyl- 1 H- 1.2,4-triazole (26a).Scheme 6. Preparation of Intermediate 26a.16a 18a 26a[111] Step 1. l-Ethyl-lH-l,2,4-triazole d8a): To an ice-cold solution of 1,2,4- triazole (5 g, 72.4 mmol) in anhydrous TEtaF (50 mL) was added ethyl iodide (7 mL, 86.9 mmol). DBU (10.8 mL, 72.4 mmol) was added dropwise to the cloudy system over 10-20 min. The reaction was allowed to slowly warm to room temperature and was stirred overnight. The mixture was filtered through a Celite pad and the filtrate was concentrated under reduced pressure to give 10 g of crude material as a yellow liquid. The crude material was Kugelrohr-distilled (at approximately 300 mtorr, 35- 40 0C) to provide 4.9 g (70%) of 18a as clear liquid.

The synthetic route of 288-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONCERT PHARMACEUTICALS, INC.; HARBESON, Scott, L.; TUNG, Roger, D.; LIU, Julie, F.; WO2011/5520; (2011); 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 956317-36-5 as follows. 956317-36-5

HATU (1.94 g, 5.09 mmol) was added to a solution of 3,3-diethoxypropan-1-amine (0.50 g, 3.40 mmol), 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (0.83 g, 4.08mmol) and N,N-diisopropylethylamine(DIPEA) (2.97 mL, 17.0 mmol) in DMF (5 mL), followedby stirring at room temperature for 15 h. An aqueous NaHCO3solution was added to the reaction solution, followed by extractionwith EtOAc. The organic layer was washed with brine and wasdried with MgSO4. The desiccant was then removed by filtration,and the solvent was distilled off under reduced pressure.The resulting residue was purified by column chromatography(20-80% EtOAc in hexanes) to yield N-(3,3-diethoxy-propyl)-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide 14 as a brown oil(1.13 g, 100%).

According to the analysis of related databases, 956317-36-5, the application of this compound in the production field has become more and more popular.

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

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., 4928-87-4

A mixture of 5-(8-azabicyclo[3.2.1]octan-3-yl)-3-(6-phenylpyridin-3-yl)-8s9- di ydropyrazolo[l,5-a]pyrido[3,2-e]pyrirnidin-6(7H)-one (43.7 mg, 0.097 mmoL), Mn02 (42.2 mg, 0.48 mmoL) in DMF (3 mL) and CH2C12 (ImL)was heated at 120C overnight. The reaction mixture was cooled to room temperature and Mn02 was removed by filtration. 1H- l,2,4-triazole-3-carboxylic acid (12.2 mg, 0.11 mmoL), EDC (34.4 mg, 0.18mmoL), HOBt (24.3 mg, 0.18 mmoL) and DIEA (93.9 uL, 0.53 mmoL) was added and the mixture was stirred at room temperature for 2h. Purification with prep-LC provided 5-(8-(4H-l,2,4-triazole-3- carbonyl)-8-azabicyclo[ 3.2.1] octan-3 -yl)-3 -(6-phenylpyridin-3 -yl)pyrazolo [1,5 -a]pyrido [3 ,2- e]pyrimidin-6(9H)-one: LCMS tR = 2.18 Min (10 mm run, UV 254rim). Mass calculated for, M+ 543.2, observed LC/MS m/z 544.2 (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; SCHERING CORPORATION; MENG, Zhaoyang; REDDY, Panduranga Adulla, P.; SIDDIQUI, M. Arshad; MANDAL, Amit, K.; LIU, Duan; ZHAO, Lianyun; MCRINER, Andrew; WO2012/27234; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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