Category: Triazoles

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 7170-01-6 as follows. 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.

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sterling Drug Inc.; US4634772; (1987); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

61-82-5, These common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, 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: To a mixture of dimedone (1 mmol), aldehyde (1 mmol), 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1 mmol)and nano-SiO2 (15 mol %) in the acetonitrile (5 mL) was stirred for appropriate time (Table 2) at 25-30 C. After the completion of the reaction as indicated by TLC, dichloromethane (CH2Cl2) was added to the solidified mixture and the insoluble catalyst was separated by filtration. Evaporation of the solvent from the filtrate and recrystallization of the solid residue from hot ethanol afforded the pure products in high yields.

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 61-82-5.

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Journal of the Iranian Chemical Society; vol. 12; 5; (2015); p. 743 – 749;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-33-1, name is 5-Bromo-1H-1,2,4-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. 7343-33-1

General procedure: To a reaction vial were added 2-bromo-5-(trifluoromethoxy)pyridine ( 1.0 g, 4.1 mmol) and 3-bromo- l – -l,2,4-triazole (0.91 g, 6.2 mmol). Lambda ,/V-Dimethylformamide (16 ml_) and cesium carbonate (2.6 g, 8.2 mmol) were added, and the vial was degassed for 5 minutes with argon. Copper(I) iodide (0.077 g, 0.41 mmol) was added, and the via l was further degassed for 5 minutes with argon. The vial was capped and heated at 100 C for 1 hour in a Biotage Initiator microwave reactor, with external IR-sensor temperature monitoring from the side of the vessel. The reaction mixture was cooled to room temperature, poured onto crushed ice (3 volumes), and extracted with ethyl acetate (3 x 150 ml_). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography using 0-40% ethyl acetate/hexanes as eluent provided the title compound as a pale brown liquid (0.40 g, 31%) : *H N MR (400 MHz, CDCI3) delta 9.01 (s, 1H), 8.39 (d, J = 2.4 Hz, 1H), 7.94 (d, J = 8.8 Hz, 1H), 7.77 (dd, J = 1.6 Hz, 8.8Hz, 1H) ; ESIMS m/z 309 ([M + H]+).

Statistics shows that 7343-33-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-1H-1,2,4-triazole.

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; SPARKS, Thomas C.; DEMETER, David A.; (242 pag.)WO2017/40742; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7343-33-1 name is 5-Bromo-1H-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. 7343-33-1

[004581 Combined 3 -bromo- 1 H-i ,2,4-triazole (29.6 g, 200 mmol), 1,2 ,4-trifluorobenzene(79.3 g, 62.70 mL, 600.0 mmol) and potassium carbonate (27.6 g, 200.0 mmol) in 500mL of DMF and heated to i000ii00 for 22 hours. The mixture was cooled and DMF removed under vacuum to dryness. 250 mL of water was added and the organics extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and evaporated. The crude mixture was purified on silica gel (220 grams column, 10-50percent Ethyl acetate:Hexanes) to afford 13g (25percent) of product JW-4c as off white solid. ?H NMR (300 MHz, DMSO-d6) oe 9.10 (d, J = 2.0 Hz, 1H), 7.77 (ddd, J = 8.9, 5.9, 3.2 Hz, 1H), 7.65 (ddd, J = 10.4, 9.3, 4.8 Hz, 1H), 7.52 – 7.41 (m, 1H) ppm. ESI-MS m/z calc. 258.95566, found 260.01 (M+i)+; Retention time: 0.79 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7343-33-1, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DAVIES, Robert, J.; CAO, Jingrong; COCKERILL, Meghan, Elise; COLLIER, Philip, Noel; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GAO, Huai; GOLDMAN, Brian, Anthony; GREY, Ronald, Lee; GRILLOT, Anne-laure; GU, Wenxin; HENDERSON, James, A.; IRARRAZAVAL, Raul Eduardo, Krauss; KOLPAK, Adrianne, Lynn; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MALTAIS, Francois; MESSERSMITH, David; PIERCE, Albert, Charles; PEROLA, Emanuele; RYU, Elizabeth Jin-Sun; SYKEN, Joshua; WANG, Jian; (706 pag.)WO2016/197009; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below.

General procedure: The tail group amines Ar-NH2 (Ar a-d) (19.5 mmol,1.1 equiv) were added to a stirring solution of 1,2,4-triazole-3-carboxylic acid 12 (2.00 g, 17.7 mmol, 1.0 equiv) in dry DMF(30 mL) at room temperature. After 5 min, TBTU (6.0 g, 18.6 mmol,1.0 equiv) and DIPEA (11.0 mL, 61.9 mmol, 3.5 equiv) were added insequence. The resulting solution was stirred at room temperaturefor 16 h. After completion of the reaction, as indicated by TLC, DMFwas removed by rotary evaporation at 30 torr and 70 C. The crudematerial was purified by methods described in each individualentry.

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:
Article; Chakraborty, Amarraj; Dou, Yali; Gibbons, Garrett S.; Grigsby, Sierrah M.; Lee, Young-Tae; Liao, Chenzhong; Mathew, Bini; Moukha-Chafiq, Omar; Nikolovska-Coleska, Zaneta; Pathak, Vibha; Reynolds, Robert C.; Schuerer, Stephan C.; Snowden, Timothy S.; Umeano, Afoma C.; European Journal of Medicinal Chemistry; vol. 189; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7343-33-1, name is 5-Bromo-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 7343-33-1, 7343-33-1

3-bromo-4H-1,2,4-triazole (98 g, 662.3 mmol) and potassium carbonate (approximately 274.6 g, 1.987 mol) were added to a 5L flask. Dimethylformamide was added followed by 2,4-difluoropyridine (approximately 152.5 g, 1.325 mol) all at once. The reaction mixture was heated to -50 ¡ãC for -16 hours then at room temperature for 48 hours. Most of the dimethylformamide was removed under vacuum and the residue was taken in ethanol (1 L) and filtered. The filtrate was evaporated under vacuum and the residue was triturated with water (-400 mL), filtered and washed with water (200 mL) to provide 76 g of crude product, which was purified by silica gel chromatography (1600 g column, 0-60percent ethyl acetate/dichloromethane) to yield 4-(3-bromo-1,2,4-triazol-1-yl)-2-fluoro-pyridine (61 g, 38percent). 1H MR (300 MHz, Methanol-^) delta 9.27 (s, 1H), 8.36 (d, J = 5.7 Hz, 1H), 7.88 ? 7.71 (m, 1H), 7.58 (t, J = 1.3 Hz, 1H) ppm

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BETHIEL, Randy Scott; CAO, Jingrong; COLLIER, Philip, N.; DAVIES, Robert J.; DOYLE, Elisabeth; FRANTZ, James Daniel; GOLDMAN, Brian Anthony; GREY, Ronald Lee; GRILLOT, Anne-laure; GU, Wenxin; KOLPAK, Adrianne Lynne; KRAUSS, Paul Eduardo; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MESSERSMITH, David; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; WANG, Jian; (491 pag.)WO2018/106646; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-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.

To a solution of 50 (1.08 g, 4.03 mmol) in DMF (20 mL) was added3-methyl-1H-1,2,4-triazole (0.469 g, 5.65 mmol) and K2CO3(0.781 g, 5.65 mmol) at r.t. The mixture was stirred at r.t.overnight and warmed to 60C for 2 h. After cooling to r.t.,water was added to the mixture. The solid was collected byfiltration, washed with water, and dried to give 51b (0.870 g,2.77 mmol, 69%) as a tan solid. 1H-NMR (300 MHz, DMSOd6) delta: 1.56 (9H, s), 2.43 (3H, s), 2.54 (3H, d, J=1.1 Hz), 8.56(1H, s), 9.10 (1H, s), 9.43 (1H, d, J=1.1 Hz). MS (ESI/APCI)m/z 315.2 [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 7170-01-6.

Reference:
Article; Mikami, Satoshi; Kawasaki, Masanori; Ikeda, Shuhei; Negoro, Nobuyuki; Nakamura, Shinji; Nomura, Izumi; Ashizawa, Tomoko; Kokubo, Hironori; Hoffman, Isaac Dylan; Zou, Hua; Oki, Hideyuki; Uchiyama, Noriko; Hiura, Yuuto; Miyamoto, Maki; Itou, Yuuki; Nakashima, Masato; Iwashita, Hiroki; Taniguchi, Takahiko; Chemical and Pharmaceutical Bulletin; vol. 65; 11; (2017); p. 1058 – 1077;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

41253-21-8, 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. 41253-21-8 name is Sodium 1,2,4-triazol-1-ide, 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.

Compound 485Synthesis of (4-hydroxy-3,5-dimethoxyphenyl)(5-thiazol-2-yl-2-[1,2,4]thiazol-1-yl-phenyl)methanone; Compound 347 [(5-(thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone] (41.7 mg, 0.1 mmol) was dissolved in DMF (3 ml), and 1,2,4-triazole.Na (27 mg) was added thereto at room temperature. The mixture was reacted at 130 C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and diluted with an EtOAc solution. The organic layer was washed with a saturated ammonium chloride solution, water, and brine. The extracted organic layer was dried over anhydrous MgSO4, and the solid substance was filtered off. The filtrate was vacuum evaporated to remove the solvent. The resulting residue was purified by column chromatography (SiO2, CH2Cl2/MeOH=40/1?10/1) to obtain Compound 485 (78.7 mg, 73%) in a form of a white solid.1H NMR (CDCl3) delta 8.375 (brs, 1H), 8.345 (dd, J=10.5, 8.40, 1H), 8.173 (d, J=2.10 Hz, 1H), 7.965 (m, 2H), 7.773 (d, J=8.40 Hz, 1H), 7.476 (d, J=3.0 Hz, 1H), 3.857 (s, 6H). MS (ESI) m/z 409 (M++H).

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

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; US2009/275575; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

To a mixture of 3-methyl- lH- l,2,4-triazole (330 mg, 3.97 mmol), 5-chloro-2-fluoro- benzaldehyde (425 mg, 2.68 mmol) in DMSO (5.0 mL) is added K2C03 (725 mg, 5.25 mmol). The reaction mixture is stirred at 100 C for 2 hours. The reaction mixture is allowed to cool to room temperature, diluted with CH2C12 (100 mL), and washed with H20 (75 mL x2). The organic layer is dried with Na2S04 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 5% MeOH in EtOAc as the eluent to afford an impure mixture of 5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-benzaldehyde plus regiosiomer (270 mg).To a mixture of 4-(2-amino-pyrimidin-5-yl)-Nl-ieri-butyl-benzene-l,2-diamine (270 mg, 1.05 mmol) and impure mixture of 5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-benzaldehyde plus regiosiomer (270 mg) in DMF (15.0 mL) is added Oxone (650 mg, 1.06 mmol) in H20 (5.0 mL). The reaction mixture is stirred at room temperature for 1.5 hours and then quenched with saturated sodium thiosulfate aq. (25 mL). The quenched reaction mixture is extracted with EtOAc (25 mL x2) and the combined organic layers are washed with H20 (50 mL x2), dried with Na2S04 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 5% MeOH in CH2C12 as the eluent to afford an impure mixture of 5-(2-amino- pyrimidin-5-yl)- l-ieri-butyl-2-[5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-phenyl]-2,3- dihydro-lH-benzimidazol-2-ol plus regiosiomer (25 mg).I l l A mixture of 5-(2-amino-pyrimidin-5-yl)- l-ieri-butyl-2-[5-chloro-2-(3-methyl- l,2,4- triazol-l-yl)-phenyl]-2,3-dihydro-lH-benzimidazol-2-ol plus regiosiomer (25 mg) in MeOH (25 mL) is heated at 70 C for 16 hours. The reaction mixture is allowed to cool to room temperature and is concentrated under reduced pressure. The residue is purified by silica gel flash column chromatography with 5% MeOH in CH2CI2 as the eluent followed by further purification using a HPLC C- 18 column with CH3CN (0.1%TFA) in H20 (0.1%TFA) as the eluent to afford 5-{ l-ieri-butyl-2-[5-chloro-2-(3-methyl- l,2,4- triazol-l-yl)-phenyl]-lH-benzimidazol-5-yl}-pyrimidin-2-ylamine (Example 37) (9 mg, 37 %) as a white solid LCMS (ESMS): m/z 459.20 (M++l) and 5-{ l-ieri-butyl-2-[5- chloro-2-(5-methyl-l,2,4-triazol- l-yl)-phenyl]- lH-benzimidazol-5-yl}-pyrimidin-2- ylamine (Example 38) (6 mg, 25 %) as a white solid. LCMS (ESMS): m/z 459.20 (M++l)

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 3-Methyl-1H-1,2,4-triazole.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; HAO, Ming-Hong; LIU, Weimin; LO, Ho-Yin; LOKE, Pui Leng; MAN, Chuk, Chui; MORWICK, Tina, Marie; NEMOTO, Peter, Allen; TAKAHASHI, Hidenori; TYE, Heather; WU, Lifen; WO2011/68821; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, These common heterocyclic compound, 288-36-8, name is 1H-1,2,3-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.

1,2,3-triazole(0.7 ), 2-iodo-benzoic acid (1.0 ), cesium carbonate (2.36 g, 7.20 mmol)Trans-N, N’-dimethyl-1,2-cyclohexanediamine (0.10 g, 0.75 mmol), cuprous iodide (0.08 g, 0.40 mmo 1), N, N-dimethyl Amide (18 mL)Were successively added to a 100 mL single-necked round bottom flask and gradually warmed to 100 C for 4 hours under nitrogen protection.The reaction was quenched, cooled, diluted with tap water and extracted with ethyl acetate (200 mL X).The aqueous layer was acidified with concentrated hydrochloric acid (rhoH- = 1 ~ 2) and extracted with ethyl acetate (200 mL x 2). The combined organic layers were dried and dried over anhydrous sodium sulfate. The filtrate was evaporated under reduced pressure and purified by column chromatography. (Dichloromethane / methanol (v / v) = 30/1) gave the title compound (yellow solid, 0.511 g, 67%)

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Wei Dehuo; Xue Yaping; Zhang Yingjun; (44 pag.)CN106674207; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics