Triazoles

Reference of 135302-13-5, These common heterocyclic compound, 135302-13-5, name is 3-Methoxy-4-methyl-1H-1,2,4-triazol-5(4H)-one, 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.

STR130 A mixture of 1.3 g (0.01 mol) of 5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 0.1 g of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1.0 g (0.01 mol) of tertbutyl isocyanate and 50 ml of acetonitrile is stirred for 12 hours at 20 C. and subsequently concentrated under a water pump vacuum. The residue is taken up in methylene chloride, and the mixture is washed with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is brought to crystallisation by trituration with petroleum ether, and the product is isolated by filtration with suction. 1.4 g (61% Of theory) of 2-tert-butyl-amino-carbonyl-5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 167 C. are obtained.

The synthetic route of 135302-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US5541337; (1996); 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. 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 252742-72-6

To a solution of N-(3-bromo-4-fluorophenyl)-N’-hydroxy-4-nitro-l,2,5- oxadiazole-3-carboximidamide (100 mg, 0.289 mmol) in DMF (2.0 mL) at 25 C was added NaSH (25 mg, 0.446 mmol). The mixture was stirred at 25 C for 30 min. Then K2C03 (40 mg, 0.289 mmol) and 3-(chloromethyl)-lH-l,2,4-triazol-5(4H)-one (58 mg, 0.434 mmol) were added. The mixture was stirred at 25 C for 30 min, diluted with sat. NaHCC (10.0 mL, aq), and extracted with ethyl acetate (10.0 mL). The organic layer was washed with brine (5.0 mL), dried over MgSC>4, and concentrated. The residue was purified by reverse phase HPLC on a GILSON 281 instrument fitted with a Phenomenex Synergi C18 (250*21.2 mm*4 muiotaeta) using water (0.2% formic acid) and acetonitrile as eluents (Mobile phase A water(0.2% Formic acid), Mobile phase B acetonitrile, Detective wavelength: 220 nm) followed by freeze-drying to give the title compound (40 mg) as a solid. lH NMR (400 MHz, CD30D) delta 7.09 (dd, J=5.8, 2.5 Hz, 1 H), 7.04 (t, J=8.7 Hz, 1 H), 6.73 – 6.81 (m, 1 H), 4.27 (s, 2 H). ESI MS m/z 430 [M+H]+

According to the analysis of related databases, 252742-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAN, Yongxin; ACHAB, Abdelghani; BIJU, Purakkattle; DENG, Yongqi; FRADERA, Xavier; GUO, Liangqin; HE, Shuwen; KOZLOWSKI, Joseph; KURUKULASURIYA, Ravi; LIU, Kun; MCGOWAN, Meredith Ann; PU, Qinglin; SCIAMMETTA, Nunzio; ZHANG, Hongjun; ZHAO, Hua; (147 pag.)WO2017/106062; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 61-82-5,Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-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: 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.

The synthetic route of 61-82-5 has been constantly updated, and we look forward to future research findings.

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

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. HPLC of Formula: C3H5N3

A mixture of 3 -methyl- IH-1, 2;4-triazole (6.83 g, 82 mmol), 2- chloro-5-mtrobenzomtrile (15 g, 82 mmol), and potassium carbonate (34.1 g, 246 mmol) in anhydrous acetonitrile (200 mL) was heated at 70 0C for 16 h. The dark brown reaction mixture was allowed to cool to rt and was poured into water (500 mL). The aqueous mixture was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified using silica gel chromatography (40-100% ethyl acetate/hexane, linear gradient) to afford 2-(3-methyl~lH-l,2,4-triazol-l-yl)-5- nitrobenzonitrile (10.9 g, 58 % yield). LC-MS (M+H)+ – 230.1. 1H NMR (500 MHz, chloroform-D) delta ppm 2.53 (s, 3 H) 8.10 (d, J-9.16 Hz, 1 H) 8.56 (dd, J-9.16, 2.44 Hz, 1 H) 8.68 (d, J-2.44 Hz, 1 H) 8.93 (s, 1 H).

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; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 956317-36-5,Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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: TEA (1.20 mL, 8.63 mmol) was added to a solution of N-ethyl-2[3-(5-fluoro-pyridin-2-yl)-1H-pyrazol-l-yl] ethanamine dihydrochloride(0.50 g, 1.63 mmol) in CHC13 (5 mL) at room temperature.5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (0.36 g, 1.79 mmol)and propylphosphonic acid anhydride (cyclic trimer) (50% solutionin DMF [approximately 1.6 mol/L], 1.32 mL, 2.12 mmol) wereadded to the reaction solution under cooling in ice water. Theresultant mixture was stirred at 50 C for 5 h. After standing untilcooled to room temperature, water was added thereto, followedby extraction with CHCl3. The organic layer was washed with brine.Then, the organic layer was dried over MgSO4 and the desiccantwas filtered off. Then, the solvent was distilled off under reducedpressure. The obtained residue was purified by column chromatography(20-80% EtOAc in hexanes) and washed with Et2O to yieldthe title compound 4a as a colorless powder (0.51 g, 75%).

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-2-(2H-1,2,3-triazol-2-yl)benzoic acid, its application will become more common.

Reference:
Article; Suzuki, Ryo; Nozawa, Dai; Futamura, Aya; Nishikawa-Shimono, Rie; Abe, Masahito; Hattori, Nobutaka; Ohta, Hiroshi; Araki, Yuko; Kambe, Daiji; Ohmichi, Mari; Tokura, Seiken; Aoki, Takeshi; Ohtake, Norikazu; Kawamoto, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1260 – 1275;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 815588-93-3,Some common heterocyclic compound, 815588-93-3, name is 1-Methyl-1H-1,2,4-triazole-5-carboxylic acid, molecular formula is C4H5N3O2, 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 mixture of 1 -methyl-1 H-1 ,2,4-triazole-5-carboxylic acid (7.0 g, 55.1 mmol) in SOCI2 (20 mL) was heated to 70 ¡ãC for 2 h. The mixture was concentrated to dryness. The residue was dissolved in NH3/MeOH (7M, 40 mL) and stirred at rt overnight. The precipitated solid was filtered off, extracted with Et20 and dried under reduced pressure to give the title compound.

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-1,2,4-triazole-5-carboxylic acid, its application will become more common.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; DEUSCHLE, Ulrich; ALBERS, Michael; HOFFMANN, Thomas; (95 pag.)WO2018/141857; (2018); 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. 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. Application In Synthesis of 4,5-Dibromo-2H-1,2,3-triazole

The reactionmixture of 4,5-dibromo-2H-1,2,3-triazole (100 mg, 0.44 mmol) and sulfuric acid(17.8 M, 0.025 mL) in tert-butanol (2.5 mL) was heated to 80 ¡ãC overnight. The reaction mixture was dilute with EtOAc and was carefully quenched with saturated aqueous NaHCO3. The two layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed withbrine, dried (over Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (0-100percent EtOAc/hexanes) to give the product.

The synthetic route of 22300-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong R.; CHO, Aesop; BUENROSTRO, Ana Zurisadai Gonzalez; HAN, Xiaochun; JABRI, Salman Y.; MCFADDEN, Ryan; QI, Yingmei; VOIGT, Johannes; YANG, Hong; XU, Jie; XU, Lianhong; (545 pag.)WO2019/75291; (2019); 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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., category: Triazoles

The mixture of 3-iodoaniline (3.70 g, 16.9 mmol), 1,2,3-triazole (3.91 mL, 67.6 mmol), K3P04 (7.17 g, 33.8 mmol), fine powder CuT (1.61 g, 8.45 mmol), ethylenediamine (0.60 mL, 8.45 mmol) in 30 mL dioxane and 15 mL DMSO were refluxed for three days to yield as the major product 3-(2H-1,2,3-triazol-2-yl)aniline and as the minor product 3-(1H- 1,2,3 -triazol- 1 -yl)aniline in ratio of about 3:1. The mixture was diluted with 400 mL EtOAc, vigorously stirred, filtered through celite, washed with brine twice, concentrated in vacuo, and subjected to flash column to isolate 3-(2H-1,2,3-triazol-2-yl)aniline (1.86 g, 68% yield).

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; WO2014/152768; (2014); 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. 1157938-97-0, name is 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Propionitrile (11 g, 0.200 mmol) was dissolved in 100 mL of anhydrous THF.Replace with nitrogen three times and slowly add at -78CBistrimethylsilyllithium200 mL (1M) of tetrahydrofuran solution, stir for 10 min, then add magnesium bromide (46 g, 0.25 mmol),After stirring for 20 min, 1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (22.3 g, 0.100 mmol) was added and slowly raised. To -50 C, then the solution is stirred for 2 hours,Until the disappearance of the raw material, 100 mL saturated ammonium chloride solution and 150 mL ethyl acetate were added.Extract twice, combine the organic phases, and wash three times with saturated saline solution.The organic phase was dried, spin-dried and passed through a column of silica gel (PE:EA=1:2) according to formula (I)23.6 g (yield: 84.9%, d.e. >99%) of de(2S,3R) and (2R,3S) white solids were mixed.The resulting solid was dissolved in 50 ml toluene, 100 ml methyl tert-butyl ether andIn a mixed solvent of 20 mL of methanol, D-10-camphorsulfonic acid (19.7 g, 84.91 mmol) was added.Heat the reaction to 60 C, react for 1h, slowly cool and cool, filter,Obtain a white solid, then add water, stir with sodium bicarbonate, extract with dichloromethane,The organic phase was concentrated to obtain the diastereoisomer of (2S,3R) 8.49 g according to formula (I)(Yield: 35.9%, e.e. >99%, d.e. >99%) LC-MS of the resulting compoundThe result of H-NMR measurement is the same as that described in Example 2.

According to the analysis of related databases, 1157938-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu Meijun; (18 pag.)CN106317044; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic 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 1001401-62-2, Recommanded Product: 1001401-62-2

EXAMPLE 2 (2-(2H- 1 ,2,3-triazol-2-yl)phenyl)(4-(4,6-dimethylpyrimidin-2-yl)- 1 ,4-diazepan- 1 -yl)methanone To a solution of l-(4,6-dimethylpyrimidin-2-yl)-l,4-diazepane hydrochloride 1-2 (1.4 g, 5.2 mmol), 2-(2H-l,2,3-triazol-2-yl)benzoic acid Int E (1.1 g, 5.7 mmol), EDC (1.5 g, 7.8 mmol), and l-hydroxy-7-azabenzotriazole (1.1 g, 7.8 mmol) in DMF (10 mL) was added DIPEA (4.5 mL, 26 mmol) and the mixture was stirred at room temperature for 16 h. The solvent was concentrated in vacuo and the crude residue was redissolved in DCM and purified by silica gel chromatography (100% hexanes, 2 min; 0-100% EtOAc/hexanes, 20 min; 100% EtOAc, 4 min) to provide Example 2 (1.5 g) as a white solid. MS (ESI) m/z: 378.4 (M+H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; ROECKER, Anthony, J.; WO2015/95111; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics