Category: Triazoles

252742-72-6, Name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, 252742-72-6, 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.

Example 408 5-[4-(2-(2-Fluorophenyl)acetyl]piperidino]methyl-2,4-dihydro-[1,2,4]triazol-3-one After adding 150 mg of 5-chloromethyl-2,4-dihydro-[1,2,4]triazol-3-one, 335 mg of 2-(2-fluorophenyl)-1-(piperidin-4-yl)ethanone hydrochloride and 180 mg of anhydrous potassium carbonate to acetonitrile, the mixture was stirred overnight at room temperature. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue and the mixture was filtered to obtain the title compound (23 mg, 7percent yield). 1H-NMR (400 MHz, DMSO-d6); delta (ppm) 1.42-1.56 (2H, m), 1.79-1.87 (2H, m), 1.98-2.07 (2H, m), 2.45-2.55 (1H, m), 2.75-2.82 (2H, m), 3.25 (2H, s), 3.89 (2H, s), 7.09-7.16 (2H, m), 7.19-7.32 (2H, m), 11.20 (1H, s), 11.26 (1H, br s).

Statistics shows that 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one is playing an increasingly important role. we look forward to future research findings about 252742-72-6.

Reference:
Patent; Ozaki, Fumihiro; Ono, Mutsuko; Kawano, Koki; Norimine, Yoshihiko; Onogi, Tatsuhiro; Yoshinaga, Takashi; Kobayashi, Kiyoaki; Suzuki, Hiroyuki; Minami, Hiroe; Sawada, Kohei; US2004/167224; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, 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 16681-65-5 as follows.

Example 156a: (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,4-dimethyloxazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol To a flask containing 1 -methyl- lH-1 ,2,3-triazole (200 nig, 2.41 mmol, prepared according to PCX int. AppL, 2008098104) was added Tl IF (20 mL) and the colorless solution was cooled to – 40 C. Then, -BuLi (2.5 M in hexanes, 1 ,0 mL, 2.5 mmol) was added drop wise which afforded a dark reddish-brown viscous solution. The mixture was stirred at -30 C for 35 minutes, then a homogeneous THF solution of (4-chioro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6- yl)(2,4-dimethyloxazol-5-yl)methanone (500 mg, 1.05 mmol, in 4 mL THF, Intermediate 87: step b) was introduced at -20 C. The reaction mixture became a dark brown color and was then placed in an ice-water bath and allowed to warm gradually to room temperature. After 45 minutes, the mixture was quenched with aqueous NH4C1 solution and extracted with EtOAc:THF (10:2), 4 x 50 mL. The combined organies were washed with brine, dried over Na2S04, filtered and concentrated to provide a brown oil. Chromatography on silica gel (3% MeOH-DCM increasing to 5% MeOH-DCM) to provide the title compound as a faint amber solid. MS m/e558.2 [M+H]+. H NMR (400 MHz, CDGU) delta ppm 8.15 (d, J = 2.0 Hz, 1H), 7.86 (d, J = 8.8 Hz, 1 1 1). 7.54 – 7.47 (m, 3H), 7.40 (d, ./ 8.1 Hz, 2H), 7.14 (s, IH), 4.35 (s, 2H), 4.10 (s, 3H), 4.03 (s, IH), 3.92 (s, 3H), 2.40 (s, 3H), 1.54 (s, 3H).Example 156a was separated by Chirai HPLC (Chiralpak AD column, 5 uM, using EtOH to provide the first eluting enantiomer as Example 156b ‘H NMR (400 MHz, CDC13) delta ppm 8.15 id. ./ 2.1 Hz, IH), 7.86 (d, J = 8.7 Hz, IH), 7.56 – 7.46 (m, 3H), 7.40 id. ./ 8.0 Hz, 21 1). 7.14 (s, IH), 4.34 (s, 2H), 4.09 is, 31 1). 3.91 (s, M l). 2.40 (s, 31 1). 1.54 (s, 3H); and the second eluting enantiomer as Example 156c H NMR (400 MHz, CDC13) delta 8.15 (d, J = 2.1 Hz, IH), 7.86 (d, J = 8.7 Hz, I H), 7.55 – 7.48 (m, 3H), 7.40 (d, J = 8.1 Hz, 2H), 7.14 (s, IH), 4.35 (s, 2H), 4.10 (s, 3H), 3.92 (s, 3H), 2.45 (s, 3H), 1.54 is, 3H).

According to the analysis of related databases, 1-Methyl-1H-1,2,3-triazole, the application of this compound in the production field has become more and more popular.

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

288-36-8, Adding some certain compound to certain chemical reactions, such as: 288-36-8, name is 1H-1,2,3-Triazole, 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 288-36-8.

[0260] Bromine (11.59 g, 73.35 mmol) was added dropwise to a 0 C solution of 2H-l,2,3-triazole (5.00 g, 72.46 mmol) in water (50 mL), and the resulting solution was allowed to warm to room temperature and stir overnight. The precipitate was collected by filtration and dried to afford 4,5- dibromo-2H-l ,2,3-triazole (8.00 g, 49%) as a white solid. MS (ESI, pos. ion) m/z 228, 226, 230 [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 288-36-8.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
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

A mixture of aldehyde (1 mmol), dimedone (1 mmol), 3-amino-1,2,4-triazole (1 mmol), and [C4(H-DABCO)2][HSO4]4 (16 mg) washeated in an oil bath (90 C) under solvent-free conditions. Aftercompletion of the reaction, as identified by TLC, using n-hexane:EtOAc (7:3) as the eluent, 10 mL of water was added and stirredfor 10 min. The catalyst was dissolved in water and the solid wasfiltered off and washed with warm EtOH, to obtain the pure targetmolecule.

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; Safari, Niloufar; Shirini, Farhad; Tajik, Hassan; Journal of Molecular Structure; vol. 1201; (2020);,
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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., 16681-65-5

Intermediate 19: step a (2,6-dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol A solution of n-butyllithium in hexanes (2,5 M, 22,5 mL, 56.3 mmol) was added dropwise by syringe to a stirring solution of 1 -methyl- IH- 1 ,2,3-triazole (5.00 g, 60.2 mmol, prepared according to PCX Int. AppL, 2008098104) in dry tetrahydrofuran (400 mL) at -55 C. The resulting off-white slurry was stirred at -45 C for 20 minutes, whereupon a solution of 2,6- dimethyl-pyridine-3-carbaldehyde (8.33 g, 61 .7 mmol) in dry tetrahydrofuran (10 mL) was added dropwise by syringe. After 5 minutes, the cooling bath was removed and the reaction mixture was allowed to slowly warm. After 45 minutes, saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (100 mL) were added. The mixture was concentrated by- rotary evaporation. The residue was dissolved in ethyl acetate (300 mL). The organic solution was washed with saturated aqueous sodium chloride solution (100 mL, containing excess solid sodium chloride). The aqueous layer was extracted with ethyl acetate (2 x 100 mL). The organic layers were combined and the combined solution was concentrated. Ether (100 mL) was added to the residue and the mixture was sonicated for 20 minutes during which time a white solid crashed out. The solids were collected by filtration. Ether (100 mL) was added to the collected solids and the mixture sonicated a second time. After 20 minutes, the mixture was filtered and the solids were collected to provide the title compound as a fine powder.

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; 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

61-82-5, A common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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.

General procedure: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

The synthetic route of 1H-1,2,4-Triazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5,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.

A solution of n-butyllithium in hexanes (2.5 M, 0.17 mL, 0.43 mmol) was added dropwise to a stirring solution of 1-methyl-1H-1,2,3-triazole (38.3 mg, 0.461 mmol, prepared according to PCT Int. Appl., 2008098104) in tetrahydrofuran (1.5 mL) at -50 C. After 20 minutes at -50 C., a solution of (4-chloro-2-ethyl-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (0.145 g, 0.307 mmol, Intermediate 25: step b) in tetrahydrofuran (1.5 mL) was added dropwise. After 5 minutes at -50 C., the flask was allowed to warm to 0 C. After 30 minutes, the mixture was partitioned between half-saturated aqueous sodium chloride solution (25 mL) and ethyl acetate (50 mL). The layers were separated and the organic layer was dried with sodium sulfate. The dried solution was filtered. Silica gel (3 g) was added to the filtrate and the mixture was concentrated by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a silica gel column for flash column chromatography purification. Elution with dichloromethane initially, grading to 10% methanol-dichloromethane provided the title compound as an off-white solid.The solid was further purified by chiral SFC (Chiralpak AD-H, 5 pm, 250x 20 mm, mobile phase: 75% C02, 25% ethanol containing0.03% isopropylamine) to provide two enantiomers. The first eluting enantiomer was Example 25b: ?H NMR (600 MHz, CDC13) oe ppm 8.30 (d, J=2. 1 Hz, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.57-7.49 (m, 3H), 7.21 (d, J=7.9 Hz, 2H), 7.17 (s, 1H), 6.18 (s, 1H), 4.91 (s, 1H), 4.49 (s, 2H), 3.95 (s, 3H), 3.40 (s, 3H), 3.00-2.90 (m, 2H), 2.30 (s, 3H), 1.35-1.28 (m, 3H); MS (ESI):mass calcd. for C28H26C1F3N60, 554.2. mlz found, 555.2 [M+H]. and the second eluting enantiomer was Example 25c: ?H NMR (600 MHz, CDC13) oe ppm 8.32 (d, J=2.1 Hz, 1H), 7.99 (d, J=8.8 Hz, 1H), 7.56-7.51 (m, 3H), 7.21 (d, J=7.9 Hz, 2H), 7.12 (s, 1H), 6.14 (s, 1H), 5.83 (s, 1H), 4.48 (s, 2H), 3.93 (s, 3H), 3.38 (s, 3H), 2.98-2.90 (m, 2H), 2.24 (s, 3H),1.34-1.27 (m, 3H); MS (ESI): mass calcd. for C28H26C1F3N60, 554.2. mlz found, 555.0 [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 1-Methyl-1H-1,2,3-triazole, 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

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. 584-13-4

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 584-13-4 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

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. 288-88-0, name is 1H-1,2,4-Triazole, A new synthetic method of this compound is introduced below., 288-88-0

To a solution of ethyl 4-fluoro-benzoate (1.68 g) in N-methyl-pyrrolidinone (10 mL) is added 1,2,4-triazole (2.5 g) and K2CO3 (1.5 g) and the mixture is heated at 190 C. in a microwave oven for 30 min. After cooling to room temperature, the mixture is acidified with 2 M aqueous HCl and the precipitate is filtered off, washed with a small amount of water and methanol/dichloromethane and dried by suction to give the acid.

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; NEUROCRINE BIOSCIENCES, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NOSSE, Bernd; BLUM, Andreas; BREITFELDER, Steffen; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; WELLENZOHN, Bernd; ASHWEEK, Neil J.; HARRIOTT, Nicole; US2013/65906; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-88-0,Some common heterocyclic compound, 288-88-0, name is 1H-1,2,4-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.

To a stiffing solution of 4-fluorobenzaldehyde (10.0 g, 80.6 mmol) in DMF (150 mL) were added K2CO3 (13.3 g, 96.7 mmol) and 1,2,4-triazole (6.67 g, 96.7 mmol) and the resultant reaction mixture was stirred at 120 C. for 6 h. After completion of reaction (by TLC), the reaction mixture was diluted with H2O and extracted with EtOAc (3*100 mL). The combined EtOAc layer was washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a solid (9.0 g, 65%): mp 145-149 C.: 1H NMR (400 MHz, CDCl3) delta 10.08 (s, 1H), 8.70 (s, 1H), 8.16 (s, 1H), 8.06 (d, J=8.0 Hz, 2H), 7.92 (d, J=8.0 Hz, 2H); ESIMS m/z 173.9 ([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 1H-1,2,4-Triazole, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics