Category: Triazoles

Related Products of 4923-01-7,Some common heterocyclic compound, 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, 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: 3-Amino-1,2,4-triazole 8a-f (1.0 mmol), o-hydroxybenzaldehyde9a-e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3¡Á1 ml), and dried. Compounds 1a-w were obtainedin a form of white solids.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-4H-1,2,4-triazol-3-amine, its application will become more common.

Reference:
Article; Guemue?, Mustafa K.; Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Chebanov, Valentin A.; Desenko, Sergey M.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1261 – 1267; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1261 – 1267,7;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 3641-13-2, A common heterocyclic compound, 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, molecular formula is C3H4N4O2, 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.

Example 2 (Synthesis of Dye 12); A solution of sodium nitrite (7.59 g; 0.11 mol) in 25 ml water was added rapidly dropwise to a slurry of 3-amino-1,2,4-triazole-5-carboxylic acid (12.81 g; 0.1 mol) in 49 g concentrated HCl (37% aq.) and 100 ml water at 0-5 C. The mixture was stirred 90 minutes at 0-5 C. The resultant diazonium slurry was added rapidly dropwise during 15 minutes to a solution of N-(2- carboxyethyl)-5-aminoquinoline (21.62 g; 0.1 mol; prepared above) in 300 ml 20% aqueous sodium carbonate at 0 C and cooled in ice bath. The mixture was stirred 5 hours, slowly warming to room temperature as the ice bath melted. The pH of the slurry was adjusted to 6.0 with concentrated HCl (37% aq.). The resulting orange precipitate was filtered and then dried at 60 C (crude yield = 49.5 g). The crude product (42.9 g) was re-dissolved in 2000 ml water. Addition of solid nickel(II) acetate tetrahydrate (7.75 g; 0.031 mol) immediately afforded a bright magenta solution of Dye 12 (lambdamax = 525 nm). The dye solution was further purified by ultra-filtration prior to evaluation.

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; LEXMARK INTERNATIONAL, INC.; EP1609823; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, 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 135242-93-2, Recommanded Product: 135242-93-2

c 3-Chloromethyl-1-methyl-1H-1,2,4-triazole (1-Methyl-1H-1,2,4-triazol-3-yl)methanol (500 mg, 4.4 mmol) (prepared using the conditions described in EP-A-421210) was added portionwise to thionyl chloride (5 ml) at 0 C. Upon complete addition the mixture was allowed to warm to room temperature, then heated at reflux for 45 minutes (gas evolution observed). Upon cooling the thionyl chloride was removed in vacuo. The residue was partitioned between dichloromethane and aqueous sodium hydrogen carbonate. The aqueous phase was further extracted with dichloromethane (x2). The combined extracts were dried (Na2SO4), filtered and evaporated to give the title chloride (570 mg), as an oil. This material was used without further purification. Data for the title compound: 1H NMR (250 MHz, CDCl3) delta 3.92 (3H, s), 4.63 (2H, s), 8.10 (1H, s). MS (ES+) m/e 133 [MH]+, 131 [MH]+.

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, (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US6355798; (2002); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

To a 100 ml round bottom flask containing 2-chloro-6-methylnicotinic acid (3 g, 17.4 mmol), copper iodide (0.16 g, 0.5 mol%), and cesium carbonate (1 1 .4 g, 35 mmol) was added a mixture of dioxane (20 ml_) and H2O (0.1 ml, 5.25 mmol). Next triazole (2.03 ml_, 35 mmol) and finally (R,R)-(-)-N,N’-dimethyl-1 ,2-cyclohexanediamine ligand (0.56 ml_, 3.5 mmol) were added. The resulting clumpy yellow slurry was stirred until evenly dispersed. Upon heating to 100 oC the reaction mixture changed from a yellow slurry to pale green. As heating progressed the slurry became less thick and was stirred more easily. The light green slurry was stirred for 4 hr at 100 oC and left to stir at room temp overnight. At this point the reaction mixture appeared as a cobalt blue slurry which was then diluted with 20 ml_ ether and 20 ml_ H2O. The resulting solution was thoroughly stirred and transferred to a seperatory funnel then the RBF was subsequently rinsed with 20 ml_ ether and H2O each. The aqueous layer was separated from the organic layer and acidified to pH 1 with 6 ml_ cone. HCI. The now brown/ lime green aqueous layer was extracted twice with EtOAc. The bright yellow organic layers were combined and dried with Na2SO4 and then cone, into a yellow powder under reduced pressure. To the yellow powder was added EtOAc to form a yellow slurry. The solids were filtered off and washed with EtOAc to give a very pale yellow powder, which was found by 1H NMR to be the Intermediate 71 (25% yield). The filtrate was cone, into a yellow solid and purified (FCC, 0-5% MeOH in DCM w/ 0.5% AcOH) to give the title product in a 20% yield. MS (ESI): mass calculated for C9H8N4O2, 204.18; m/z found 205.3 [M+H]+ 1 H NMR (400 MHz, CD3OD): 8.21 – 8.18 (m, 1 H), 7.98 (s, 2H), 7.51 (d, J = 7.9 Hz, 1 H), 2.64 (s, 3H).

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

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

Application of 22300-52-3, 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. 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

Into a 5000-mL 3-necked round-bottom flask, was placed 4,5-dibromo-2H-1,2,3-triazole (301 g, 1.33 mol, 1.00 equiv), potassium carbonate (92.5 g, 669.27 mmol, 0.50 equiv) and NMP (3000 mL). This was followed by the addition of 1-chloropropan-2-one (148 g, 1.60 mol, 1.21 equiv) dropwise with stirring at 0¡ã C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 9000 mL of water. The solid was collected by filtration and dried in an oven. This resulted in 346 g (92percent) of 1-(dibromo-2H-1,2,3-triazol-2-yl)propan-2-one as a white solid.

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, 4,5-Dibromo-2H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline, 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. Formula: C8H8N4

A mixture of tert-butyl (1S,2R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate (80 mg, 0.227 mmol), 3-(2H-1,2,3-triazol-2-yl)aniline (50 mg, 0.312 mmol), K2CO3 (60 mg, 0.434 mmol), BINAP (20 mg, 0.032 mmol) and Pd(OAc)2 (10 mg, 0.044 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 100 C for 20 h. Water and EtOAc were added. Organic phase was separated. The aqueous phase was extracted with EtOAc again. The combined organic phases were dried over Na2SO4, concentrated in vacuo to give a crude tert-butyl (1S,2R)-2-(6-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate (170 mg).

The synthetic route of 626248-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, 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 16681-70-2 as follows.

[0622] (2S,4S)-4-Amino-5-biphenyl-4-yl-2-cyanomethylpentanoicacid ethyl ester (70 mg, 199 f.tmol) was combinedwith DMF (1 mL), HATU (76 mg, 199 flillOI), DIPEA (104f.LL, 596 f.tmol), and 3H-[1,2,3]triazole-4-carboxylic acid (22mg, 199 flillOI) and the mixture was stirred at room temperaturefor 20 minutes. The solvent was evaporated and the crudemixture was purified by normal phase chromatography(0-100% EtOAc/hexanes) to yield Compound 1 (60 mg).

According to the analysis of related databases, 16681-70-2, the application of this compound in the production field has become more and more popular.

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

Application of 1455-77-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1455-77-2 name is 3,5-Diamino-1,2,4-triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

1H-1,2,4-Triazole-3,5-diamine (12.4 g, 0.125 mol) was dissolved in AcOH (50 ml), and diethyl 2-(ethoxymethylene)malonate (32.5 g, 0.15 mol) was added. The solution was refluxed overnight, then cooled, filtered, and dried to give Key Intermediate VI (22 g, 79percent) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Diamino-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; European Molecular Biology Laboratory; F. Hoffmann-La Roche AG; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SAUVAITRE, Thibault; SIMON, Celine; MORICE, Christophe; GIETHLEN, Bruno; LANGER, Thierry; SMITH, Mark; SO, Sung-Sau; CLASSEN-HOUBEN, Dirk; BUSCHMANN, Helmut; US2013/317022; (2013); 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1,2,4-Triazole-3-carboxylic acid

To a mixture of 1H-1,2,4-triazole-3-carboxylic acid (118 mg, 1.044 mmol) and HATU (429 mg, 1.13 mmol) in DMF (2.2 mL) was added DIPEA (325 muL, 1.87 mmol) and the mixture was stirred for 15 min. Then tert-butyl 2,2-dimethylpiperazine-1- carboxylate (200 mg, 0.93 mmol) is added followed by DIPEA (240 muL, 1.38 mmol) and the mixture was stirred for another 90 min. Saturated NH4Cl was added (5 mL), followed by EtOAc (10 mL). The layers were separated and the aqueous layer extracted with EtOAc (2 x 5 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-15% MeOH: DCM affording the title compound (263 mg, 91% yield) as an off-white solid. ESI-MS m/z calc.309.18008, found 310.35 (M+1)+ Retention time: 1.22 minutes using method C

According to the analysis of related databases, 4928-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SAYEGH, Camil Elie; STURINO, Claudio; FOURNIER, Pierre-Andre; LACOSTE, Jean-Eric; DIETRICH, Evelyne; MARTEL, Julien; VALLEE, Frederic; (494 pag.)WO2016/154075; (2016); 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 7343-33-1 as follows. Recommanded Product: 5-Bromo-1H-1,2,4-triazole

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 wascooled to room temperature (RT), 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 provided the title compound as an off-white solid (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]+)

According to the analysis of related databases, 7343-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; US2014/275556; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics