Category: Triazoles

These common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-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. 7411-23-6

In a 250 mL round bottomed flask sodium hydride (60% dispersion in mineral oil) (264 mg, 6.61 mmol) was added to a colorless solution of 3,5-dibromo-1H-1,2,4-triazole (Int-1, 1 g, 4.41 mmol) in DMF (22 ml). The resulting suspension was stirred at room temp during 30 min and 3-(bromomethyl)-3-methyloxetane (873 mg, 5.29 mmol) was added and the reaction was stirred at 40C over night.The reaction mixture was poured into 50 mL H20 and extracted with EtOAc (3 x 50 mL). The organic layers were washed with sat NaCl (3 x 50 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a colorless liquid (1.35 g, 98.5 % yield). MS (ES+) m/z: 311.9 [(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 7411-23-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

956317-36-5, A common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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.

The 5 – methyl -2 – (2 H – 1, 2, 3 – triazole -2 – yl) benzoic acid (2.03 g, 10 mmol) is added to the 100 ml round bottom flask in the single port, for anhydrous dichloromethane (20 ml) dissolved, then slowly adding thionyl chloride (15 ml, 200 mmol) and pyridine (0.15 ml, 2 mmol). The reaction solution gradually heating to reflux, the reaction 3 hours after stopping the reaction, cooling, slowly evaporating the solvent under reduced pressure, the obtained product can be directly into the next step.

The synthetic route of 956317-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Lao Jinhua; Nie Biao; Xu Juan; (35 pag.)CN107759620; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, 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 423165-07-5. 423165-07-5

General procedure: To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.

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 exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane.

Reference:
Article; Viveka, T. Lakshmi; Sharada, L. Nalanda; Asian Journal of Chemistry; vol. 30; 9; (2018); p. 2029 – 2034;,
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

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

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

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

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

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 6086-21-1 as follows. 6086-21-1

(a) To a solution of 19.6 g (0.236 mol) of 1-methyl-1,2,4-triazole in 350 ml of ether at -78¡ã C. under argon was added n-butyllithium (91 ml, 0.236 mol, 2.5M in hexane) within a 30 min period and the mixture was stirred at -78¡ã C. for 2 h, and followed with the addition of 17.3 g (0.236 mol) of DMF in 45 ml of ether. The mixture was slowly warmed to 0¡ã C., and was stirred at 0¡ã C. for 2 hours, then 25 g of silica gel was added to the mixture. The whole suspension was packed on a silica column with methylene chloride and the eluent (methylene chloride/ether, 4:1) was concentrated to afford 17.75 g (67.7percent) of 1-methyl-1,2,4-triazolyl-5-carboxaldehyde, as a yellow oil.

According to the analysis of related databases, 6086-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sterling Winthrop Inc.; US5569655; (1996); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide, 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. 3641-08-5

EXAMPLE 6 Preparation of 1(and 2 and 4)-Adamantylcarbonyl-s-triazole-3-carboxamide To a cooled, stirred mixture of 2 g. of 1,2,4-triazole-3-carboxamide and 5.4 g. of adamantylcarbonyl chloride in 125 ml. of anhydrous diethyl ether is added rapidly 2.75 g. of triethylamine. The cooling bath is removed and the mixture is stirred at room temperature for 23.5 hours. The mixture is filtered and the solid is washed successively with diethyl ether, cold water, diethyl ether and dried in vacuo for 3 hours yielding 4.5 g. of colorless solid. This solid is extracted with hot dry acetonitrile, cooled and washed with acetonitrile yielding 0.4 g. of colorless crystals. The remaining 3.5 g. of acetonitrile insoluble solid is further extracted with acetonitrile, yielding an additional 0.6 g. of product, m.p. 213-216 C. (dec.).

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 3641-08-5.

Reference:
Patent; American Cyanamid Company; US4006159; (1977); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics