Triazoles

Reference of 41253-21-8, A common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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 suspension of 18 g sodium triazolide in 170 g DMF was heated to 90C. At this temperature 47,3 g of 78,3 wt-% racemic (3SR,7RS)-7-(4-chloro-benzyl)-4,4-dimethyl-1 – oxa-spiro[2.4]heptane (racemic mixture of IXa/IXb), prepared according to example 10, were added, followed by stirring of the mixture for 6 h at 90C. Then 129 g of the DMF were distilled off at 50C/3mbar. To the resulting residue 87 g water and 320 g of MCH were added and the phases were separated at 65C. The aqueous phase was extracted with 100 g fresh MCH at 65C. The combined MCH solutions were washed three times with 80 g water. Thereafter the MCH solution was concentrated to 309 g at 80C/500-400 mbar. For crystallization the solution was cooled from 80C to 0C with a rate of 6K/h. After stirring overnight the product was isolated by filtration. The filter cake was washed twice with 50 g of ice-cold MCH and then dried in a vacuum dryer at 50C/8 mbar. Thus 36.4 g of cis-metconazole were obtained, having a purity of 97.1 %, determined by quantitative GC-analysis, corresponding to a yield of 74.5%. Melting point: 1 12C H-NMR (500 MHz, CDCI3): delta/ppm = 0.62 (s, 3H), 1 .04 (s, 3H), 1 .28-1 .48 (m, 2H), 1 .64-1 .82 (m, 2H), 2.25 -2.52, (m, 3H), 3.87-3.94 (s, broad OH), 4.19 (d, 1 H) 4.28 (d, 1 H), 7.10 (d, 2H), 7.20 (d, 2 H), 7,.98 (s, 1 H), 8.21 (s, 1 H) 3C-NMR (125 MHz, CDC ): delta /ppm = 21 .94 (q), 25.08 (q), 27.20 (t), 35.83 (t), 38.07 (t), 46.29 (s), 46.86 (d), 53.92 (t), 82.37 (s), 128.36 (d, 2C), 130.19 (d, 2C), 131.46 (s), 139.71 (s), 144.30 (d), 151.37 (d)

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; BASF AGRO B.V., ARNHEM (NL), ZUeRICH-BRANCH; ZIERKE, Thomas; KEMPER, Paul; WO2013/117629; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 584-13-4, 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. 584-13-4, name is 4H-1,2,4-Triazol-4-amine belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

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

Reference:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 288-88-0, name is 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. name: 1H-1,2,4-Triazole

(ii) Preparation of crude anastrozole of formula-I; Into a 10L, three-necked RB flask was charged l.4kg of above crude compound of formula-V and 7L of anhydrous DMF. The reaction mass was stirred for 30min and added 0.65kg of solid sodium triazole (prepared by reaction of molar quantities of 1,2,4- IH-triazole and sodium hydroxide in isopropanol at reflux temperature and isolated by filtering of the reaction mass at room temperature) in lots keeping the temperature below 25 C. The reaction mass was maintained under stirring at this temperature for 4hr. HPLC of the reaction mass indicated the absence of starting material. The reaction mass was transferred into a 50L flask containing 21L of water and stirred for 30min. Reaction mass was extracted with toluene (2 x 3L and 1 x 1L). Toluene layers were combined and . washed with water (2 x 2L). Toluene was distilled of from the filtrate under vaccum to get 1.2kg of crude anastrozole.; (ii) Preparation of crude anastrozole; Into a 1 L, three-necked RB flask was charged 60g of sodium triazole monohydrate (prepared by reaction of molar quantities of 1,2,4-IH-triazole and sodium hydroxide in isopropanol at reflux temperature and isolated by filtering of the reaction mass at room temperature) and 200ml of dry DMF under nitrogen atmosphere. The reaction mass was cooled to 20 C. A solution of the above bromo compound of formula-V (140g) in toluene (200ml) was added to the reaction mass over a period of 2hr. The reaction mass was maintained at this temperature until the completion of reaction. The reaction mass was transferred into 3L flask containing 1.5L of water and stirred for 30min. Reaction mass was extracted with toluene (2 x 300ml and 1 x 100ml). Toluene layers were combined and washed with water (2 x 200ml). Toluene layer was treated with activated carbon (5g) and filtered. Toluene was distilled of from the filtrate under vaccum to get 130g of crude anastrozole.

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

Reference:
Patent; NATCO PHARMA LIMITED; PULLA REDDY, Muddasani; VENKAIAH CHOWDARY, Nannapaneni; WO2005/105762; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1001401-62-2, 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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

Step (vii): tert-Butyl N-{4-[(4-methoxyphenyl)methoxy]-2-[2-(2H-1,2,3-triazol-2-yl)benzamido]cyclopentyl}carbamate To a solution of tert-butyl N-{2-amino-4-[(4-methoxyphenyl)methoxy]cyclopentyl}-carbamate (1.71 g, 5.08 mmol) in dry DMF (17 ml) was added 2-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 1.06 g, 5.59 mmol), HATU (2.90 g, 7.62 mmol) and triethylamine (2.13 ml, 15.25 mmol). The reaction was stirred at room temperature for 72 hours then partitioned between ethyl acetate and water. The organics were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (silica, 0-100% ethyl acetate petrol) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.37 (s, 9H), 1.46-1.59 (m, 1H), 1.58-1.77 (m, 1H), 1.86-1.97 (m, 1H), 2.18-2.37 (m, 1H), 3.67-3.79 (m, 4H), 3.83-4.01 (m, 2H), 4.32 (s, 2H), 6.85-6.95 (m, 2H), 7.17-7.31 (m, 2H), 7.44-7.54 (m, 2H), 7.55-7.66 (m, 1H), 7.76 (s, 1H), 7.96-8.05 (m, 2H) MS ES+: 508

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1186050-58-7, 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. 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

To a 3-necked, 3 L, round- bottomed flask equipped with a nitrogen line, temperature probe, heating mantle, reflux condenser, mechanical stirrer, and 1 N aq. NaOH scrubber were added 2-fluoro-6-[1 ,2,3]triazol-2-yl-benzoic acid (Intermediate 12, 120.98 g, 75 wt%, 90.74 g actual, 438 mmol) and toluene (1 L). The mixture was warmed to 50 oC for 1 h with stirring. The mixture was then cooled to 25 oC and thionyl chloride (47.9 mL, 657 mmol) was added. The mixture was warmed back to 50 oC and held for 1 h. During this time, in a separate 5 L jacketed reactor equipped with a mechanical stirrer and temperature probe were added toluene (600 mL), aqueous sodium carbonate (185.7 g, 1 .75 mol in 1 .6 L water), and 2- (4,6-dimethyl-pyrimidin-2-yl)-octahydro-pyrrolo[3,4-c]pyrrole*HOAc(Intermediate 23, 122 g, 438 mmol). This biphasic mixture was cooled to 0 oC. After cooling to 0 oC, the original slurry was poured through a filter and over the stirring biphasic mixture of amine and aqueous sodium carbonate. The mixture was allowed to warm to room temperature. After 2 h, additional 2-(4,6- dimethyl-pyrimidin-2-yl)-octahydro-pyrrolo[3,4-c]pyrrole*HOAc (4 g, 14 mmol) was added and the mixture was stirred for 30 additional minutes. At the end of this period, the layers were separated and 100 mL of methanol were added to the organic layer. The organic layer was dried over MgSO , filtered, and concentrated to a white solid. This solid was taken up in ethanol (1 .4 L) and warmed to 77 oC. The mixture was then cooled to 55 oC and seeded with previously crystallized material. (Note: The seeds were generated from slurrying the initial product in 2-propanol at room temperature [100 mg/mL]). The mixture was cooled to room temperature at a rate of 5 oC per hour. After stirring at room temperature for 14 h, the mixture was filtered and dried to provide the final product as a white crystalline solid (136.84 g, 74%). 1H NMR (400 MHz, CDCIs): 7.88 – 7.78 (m, 1 .78H), 7.75 – 7.69 (s, 1 .22H), 7.51 – 7.43 (m, 1 H), 7.17 – 7.1 1 (m, 1 H), 6.30 – 6.28 (m, 1 H), 4.03 – 3.48 (m, 7H), 3.29 – 3.21 (m, 1 H), 3.15 – 2.92 (m, 2H), 2.30 (s, 6H). MS (ESI) mass calcd forC21 H22FN7O, 407.19; m/z found, 408 [M+H]+. Anal, calcd. for C21 H22FN7O C, 61 .90, H, 5.44, N, 24.06; found C, 61 .83, H, 5.42, N, 24.08

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, 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHAI, Wenying; LETAVIC, Michael, A.; LY, Kiev, S.; PIPPEL, Daniel, J.; RUDOLPH, Dale, A.; SAPPEY, Kathleen, C.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; SOYODE-JOHNSON, Akinola; STOCKING, Emily, M.; SWANSON, Devin, M.; WO2011/50198; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 4928-88-5, 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. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 8 A mixture of methyl 1,2,4-triazole-3-carboxylate (26.4 g, 0.21 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (60.2 g, 0.19 mole) was melted and then 1.1 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 5 hours, while maintaining the temperature of the reaction mixture at 95+-5¡ã C. And then, the reaction mixture was crystallized with 180.5 ml of methanol to give 68.9 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 95percent).

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

Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); 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. category: Triazoles

300 mg of intermediate 31, sodium hydride(60%, oil) 45 mg and DMF 1.3 mL, 116 mg of 3-chloro-1 H-1,2,4-triazole was added under ice cooling. After the reaction mixture was stirred for 20 hours under ice cooling, water was added to the reaction mixture,And extracted with ethyl acetate. The obtained organic layer was washed with water,After drying with anhydrous sodium sulfate, it was dried under reduced pressure.The obtained residue was subjected to silica gel chromatography,240 mg of the present compound 1299 described below was obtained.

The synthetic route of 6818-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical; Ikari, Kaori; (123 pag.)JP2019/6686; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, name is 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. Recommanded Product: 288-36-8

Add 1.1 kg of acetone to the 5L reaction flask.131g 2-iodo-5-methylbenzoic acid,Stir and dissolve,Add 350g of anhydrous potassium carbonate,After heating to reflux (55-60 C) for half an hour, add 114g 1,2,3-triazole,2.4 g of cuprous iodide.The reaction was kept under reflux (55-60 C) for 8 hours, sampled, and sampled once every 1 h. After the reaction was completed, it was cooled to room temperature for filtration, and the filter cake was washed twice with 120 g of acetone to obtain a white solid at room temperature (20-30 C). The white solid was dissolved in 1.3 kg of purified water and stirred.After 30 min, hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1.5-2.0 to obtain a large amount of white solid. It was stirred for 1-2 hours, filtered, and the filter cake was washed twice with purified water. The resulting solid was dried to dryness at 50 ¡À 5 C to give a crude compound.Add 1 compound of crude product, 0.2 kg of absolute ethanol and 0 kg of purified water to a 1 L reaction flask, and warm to 75-80 C.Clear, heat for half an hour, cool to 0-5 C, filter, filter cake with a cold ethanol solution rinse, to obtain a white solid compound 1 boutique.The compound 1 was placed in a blast drying oven at a temperature of 55 C ¡À 5 C and dried for 5 h. Sampling, sampling every 2h 1Time, until the test (rapid moisture analyzer: 105 C, 10 min) loss on drying ? 0.5%, get Suwoleisheng intermediate products -Compound 1 was fine white crystalline solid 86 g, yield: 93%. Purity: 99.91%, Cu < 5 ppm. The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Yangzijiang Pharmaceutical Group Co., Ltd.; Zou Yiquan; Xu Jingren; Cai Wei; Xuan Jingan; Chen Lingwu; Ji Ye; Zhu Yunlong; Liu Jinfeng; Hu Tao; (8 pag.)CN109810067; (2019); 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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C2H3N3

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

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 288-36-8.

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

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, belongs to Triazoles compound, 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 16681-70-2, Product Details of 16681-70-2

[0824] lH-1,2,3-triazole-5-carboxylic acid (3.4 mg, 30f.tmol) was combined with HATU (11 mg, 30 f.tmol) in DMF(0.3 mL) and stirred at room temperature for 10 minutes;DIPEA (1 eq.) was added and the mixture was stirred for 1minute. Compound 2 (1 0 mg, 30 f.tmol) was dissolved in DMF(0.5 mL) and DIPEA (5.2 f.LL, 30 fllllOl) was added, followedby addition of the activated acid solution. The mixture wasstirred at room temperature for 30 minutes, after which timeLCMS indicated desired product formation. Half of the crudeproduct was purified using reverse phase chromatography toyield Compound a (4.3 mg) as a TFA salt. MS m/z [M+Htcalc’d for C27H31ClFN50 4 , 544.21; found 544. Half of thecrude product was used in the next step without purification.

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; 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