Category: Triazoles

Adding some certain compound to certain chemical reactions, such as: 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide, 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 3641-08-5. 3641-08-5

A stirred mixture of 1H-1,2,4-triazole-3-carboxamide (500 mg, 4.46 mmol) in 1,2-dichloroethane (4.46 mL) treated at room temperature with 2,6-lutidine (2.08 mL, 17.84 mmol) and triethylsilyl trifluoromethanesulfonate (3.03 mL, 13.38 mmol) and heated under a nitrogen atmosphere at 50C. After 4 hours of heating the reaction solution allowed to cool to room temperature and diluted with dichloromethane (25 mL), washed with water (25 mL), 0.5M hydrochloric acid (25 mL), water (25 mL), dried over MgSO4, filtered, and evaporated to solid. The solid was flash chromatographed (silica gel, 10-65% ethyl acetate:hexane) to give the product as a white solid (683 mg).1H NMR (CDCl3, 500MHz, ppm) 0.89 (q, J=8Hz, 6H, CH2), 1.03 (t, J=8 Hz, 9H, CH3), 6.77 (s, 1H, NH), 8.63 (s, 1H, triazole H-5).LC/MS m/z (positive ion scan) M+l= 227.20.

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 2H-1,2,4-Triazole-3-carboxamide.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SCYNEXIS, INC.; GREENLEE, Mark, L.; WILKENING, Robert; APGAR, James; SPERBECK, Donald; WILDONGER, Kenneth, James; MENG, Dongfang; PARKER, Dann, L.; PACOFSKY, Gregory, James; HEASLEY, Brian, Haid; MAMAI, Ahmed; NELSON, Kingsley; WO2010/19204; (2010); A1;,
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. 288-36-8

To a solution of 3-chloro-4-fluoronitrobenzene (1.2 g, 6.836 mmol) and 2H-1,2,3-triazole (0.567 g, 8.203 mmol) in anhydrous DMA (5 mL) was added K2CO3 (1.89 g, 13.7 mmol). The reaction mixture was stirred at 55 C. overnight. The reaction was concentrated to give a crude oil. The crude product was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100/0 to 20/80) to give compound 4d (1 g, 65.1%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.88-8.02 (m, 3H), 8.28 (dd, J=8.93, 2.54 Hz, 1H), 8.49 (d, J=2.21 Hz, 1H).

Statistics shows that 288-36-8 is playing an increasingly important role. we look forward to future research findings about 1H-1,2,3-Triazole.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, Adding a certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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 7170-01-6.

41. 5-(3-Methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2-(1H)-one A stirred mixture containing 13.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 20 g of 3-methyl-1H-1,2,4-triazole and 75 ml of N-methylpyrrolidinone was heated in an oil bath at 170-180 C. for 18 hours and then cooled to room temperature whereupon a tan solid crystallized out. The mixture was diluted by adding 125 ml of water and the separated solid was collected, washed with water, air-dried and combined with another 1.2 g sample of the same material obtained in another run starting with 2.25 g of 5-bromo-1,6-naphthyridin-2(1H)-one. The combined solids were recrystallized from dimethylformamide and dried in an oven at 95-100 C. for three days to yield 6.1 g of 5-(3-methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >300 C.

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

Reference:
Patent; Sterling Drug Inc.; US4657915; (1987); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

584-13-4,Some common heterocyclic compound, 584-13-4, name is 4H-1,2,4-Triazol-4-amine, molecular formula is C2H4N4, 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: 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.

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

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

The chemical industry reduces the impact on the environment during synthesis 6818-99-1, name is 3-Chloro-1,2,4-triazole, I believe this compound will play a more active role in future production and life. 6818-99-1

200 mg of intermediate 35, 60% sodium hydride(Oily) 37 mg, and DMF 2 mL,Under ice-cooling, 67 mg of 3-chloro-1H-1,2,4-triazole was added. After stirring for 2.5 hours under ice cooling,Saturated multilayer aqueous solution was added to the reaction mixture,And extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate.The obtained organic layer was dried under reduced pressure.The obtained residue was subjected to silica gel chromatography,171 mg of the present invention compound 246 described below was obtained.

The chemical industry reduces the impact on the environment during synthesis 6818-99-1. I believe this compound will play a more active role in future production and life.

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

7411-23-6, The chemical industry reduces the impact on the environment during synthesis 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

To a solution of 2 (15 g, 66.1 mmol) in acetonitrile(80 mL) was slowly added N,N-diisopropylethyamine(8.0 g, 61.9 mmol) followed by benzyl bromide(12.4 g, 5.8 mmol) in dimethyl foramide (15 mL). It was stirred for 12 h at 80C. Progress of the reaction was monitored by TLC. After completion of the reaction, volatiles were evaporated under reduced pressure. Into the residue, water was added and the reaction mass extracted with dichloromethane(3¡Á100 mL). Combined organic phase was dried over anhydrous magnesium sulphate, concentrated todryness and further purified by column chromatography to afford 6 as a white solid (18 g,80% yield). m.p. 67.4-68; IR (KBr): 3088, 2948,1586, 14.96, 1453, 1434, 1416, 1259, 1059 cm-1;1H NMR (400 MHz, CDCl3): 5.32 (s, 2H), 7.31-7.39(m, 5H); 13C NMR (100 MHz, CDCl3): 53.7, 128.0,128.8, 129.0, 129.4, 133.6, 140.3 (1H and 13C patterns match with the litereature value)22.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Roy, Bhairab Nath; Singh, Girij Pal; George, Shaji K.; Lathi, Piyush S.; Agrawal, Manoj K.; Trivedi, Anurag; Mishra, Madhan; Singh, Gajendra; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 53; 5; (2014); p. 610 – 618;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 584-13-4, name is 4H-1,2,4-Triazol-4-amine, 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. 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.

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, 584-13-4, other downstream synthetic routes, hurry up and to see.

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

288-36-8, 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 288-36-8 as follows.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-2, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. A solution of the acid (3.56 g, 17.52 mmol) in 150 mL of DCM was stirred and cooled to 00C. The solution was treated with oxalyl chloride (1.9 mL, 21.9 mmol) and DMF (68 muL, .878 mmol). The solution was slowly warmed to room temperature and stirred overnight. Solvent was concentrated and the resulting solid was azetroped with DCM and concentrated to provide A-4 as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 288-36-8, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; FLORES, Broc; SCHREIER, John, D.; WO2010/48016; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, The chemical industry reduces the impact on the environment during synthesis 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a reaction of H-, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and 2- (l//-indol-3- yl)ethanamine (0.34 mg, 2.1 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into iced water and extracted with DCM (2 x 50 mL). The DCM phase was washed with ice cold water (2 x 100 mL). The DCM phase was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and chromatographed on silica gel using MeOH and DCM (10:90) as eluents to get the desired amide 19 (193.3 mg, 38 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.90-14.48 (m, 1H), 10.82 (s, 1H), 8.80-8.13 (m, 2H), 7.61 (d, J= 7.6 Hz, 1H), 7.35 (d, J= 8 Hz, 1H), 7.21-7.18 (m, 1H), 7.11-7.05 (m, 1H), 7.04-6.96 (m, 1H), 3.61-3.53 (m, 2H), 2.97 (t, J= 7.6 Hz, 2H) ppm. MH+ = 256.2 m/z. The chemical industry reduces the impact on the environment during synthesis 1,2,4-Triazole-3-carboxylic acid. I believe this compound will play a more active role in future production and life. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, 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. 41253-21-8

10.0 g of [COMPOUND 1] and 100 ml of tert-butyl acetate are loaded in a flask. The resulting suspension is kept under stirring at ambient temperature.8.30 g of N-bromosuccinimide (NBS) followed by 220 mg of catalyst azobisisobutyronitrile (AIBN) are then added. At this point, the resulting mixture is heated and kept at a temperature of 65-75C for 2-4 hours.The reaction quenching is performed by lowering first the temperature of the reaction mixture to 30-40C and then adding 50 ml of a 5% solution of sodium metabisulphite.At this point the organic rich phase is separated from thewater phase and then washed with distilled water.80 ml of dimethylformamide (DMF) are added to the rich solution, after the latter has been concentrated in a vacuum. The solution thus obtained is re-distilled to eliminate theresidual t-butylacetate solvent. 4.47 g sodium 1,2,4-triazole are added to the same solution, after the latter has been brought to a temperature of 0-25C (preferably 5-10C). The reaction mixture thus obtained is kept under stirring for 1-2 hours.The reaction is quenched by the addition of 100 ml toluene and 125 ml distilled water. After separation of the phases, the rich organic phase is treated with a. water solution HC1 0.lM.After separation of the phases, 1 g of carbon is added to the resulting organic phase and it is kept under stirring at ambient temperature.After filtering, the clarified organic phase is extractedtwice with 100 ml of HC1 2M. The rich water phase, containinghigh purity dissolved anastrozole, is lastly back-washed with toluene.Maintaining a temperature below 15C, a solution of NaOF{ at30 by weight is added to the rich acid solution in 60-90minutes until pH 1 is reached. The mixture is then left in crystallization break at 0-5C for 2 hours. A solution of NaOI-{ 0.5 M is then added until a pH of between 2.5 and 3.5 is obtained. The resulting suspension is then left in break at0-5C for a further 2 hours. A last quantity of NaOH 0.5 M solution is then added until a final pH of between 5 and 7 is reached, followed by a last break atThe product is lastly filtered, washed with distilled waterand then dried in a vacuum at a temperature of 50C.In this way 6.3-6.6 g of pharmaceutical grade anastrozole are obtained from 10 g of commercial grade ANA-3.In particular, the product has:anhydrous titre: 99.16% ¡Â 101.10%; KF<0 .1%;total impurities: 0.21% ¡Â 0.26% 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, 41253-21-8, other downstream synthetic routes, hurry up and to see. Reference:
Patent; CORDEN PHARMA LATINA S.P.A. CON SOCIO UNICO; ANTONINI, Alberto; OLIVIERI, Lauso; SACCHITELLI, Doralinda; WO2014/184754; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics