Triazoles

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. 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde

To a 50 mL flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.45 g, 3.37 mmol, Intermediate 47: step d) was added THF (25 mL) at room temp which resulted in a colorless homogeneous mixture. The solution was cooled to -70 C. which remained homogeneous and then n-BuLi (2.5 M in hexanes, 1.3 mL, 3.25 mmol) was added dropwise. The color of the solution became a dark reddish-brown color. After 2 minutes, 1-methyl-1H-1,2,3-triazole-5-carbaldehyde (580 mg, 5.22 mmol, in 3 mL THF, Intermediate 50: step a) was introduced and the color of the mixture went from dark brown to greenish to a yellow color within about 2 minutes. The mixture was allowed to warm to -20 C. over 45 minutes at which time the contents were quenched with aqueous NH4Cl. The mixture was diluted further with water and extracted with EtOAc (5*40 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a yellowish oil. The crude material was chromatographed on silica gel (5% CH3CN-DCM increasing to 30% CH3CN+2% MeOH) to give the title compound as an off white foam.

The synthetic route of 202931-88-2 has been constantly updated, and we look forward to future research findings.

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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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 6523-49-5, Safety of 4-(1,2,4-Triazol-1-yl)aniline

To a solution of formamidine from Step 4 (257mg, 0.653mM) in acetic acid (3ml) was added the 4-triazolylaniline (115mg, 0.73mM). The reaction was heated to 125C for Ih. The mixture was cool down basified with 15ml of 2N NaOH and extracted with ethylacetate. After drying over magnesium sulphate these organics phases were concentrated to a yellow solid. The solid was triturated with DCM / Et2O / petrol and isolated as a yellow solid (163mg, 44%). 1H NMR (D6-DMSO) delta 10.07 (IH, broad s), 9.29 (IH, s), 8.83 (IH, s), 8.64 (IH, s)8.26 (2H, m), 8.07 (2H, m), 7.85 (5H5 m), 7.69 (IH, d, J 10Hz)5 7.35 (IH5 dd, J 10Hz55Hz), 4.22 (2H, t, J 7.5Hz)5 2.46 (6H, m, obscured by H2O), 2.08 (2H5 1, J 7.5Hz)5 1.70(4H , m).LC-MS rt 2.13 m/z 509 ES+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1,2,4-Triazol-1-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); 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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-1H-1,2,4-triazole

Diacetoxycopper (18.4 g, 101.4 mmol), bromo-triazole (lOg, 67.6 mmol), and 4A molecular sieves (250 mg, 0.33 mmol) were mixed in DCM, to which 4-difluorophenyl)boronic acid (14.9g, 94.6 mmol), pyridine (10.9 mL, 135.2 mmol) was added. The mixture was stined at RT under air for 3 days. LCMS showed that no starting material remaining and desired product was formed. The reaction was filtered and the solid was washed with additional DCM (200 ml). The combined organic layer was concentrated with silica gel and dry-loaded to purify on silica gel (240 grams column, 10-90percent ethyl acetate:hexanes) to afford 10.5 g (60percent) of desired product JW3-c. ?H NMR (400 MHz, DMSO-D6) oe 9.30 (s, 1H), 8.08 – 7.96 (m, 1H), 7.77 – 7.62 (m, 2H) ppm. ESI-MS m/z calc. 25 8.95566, found 260.32 (M+1)+; Retention time: 0.96 minutes.

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; 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

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. 64922-04-9, name is Ethyl 1H-1,2,4-triazole-5-carboxylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 1H-1,2,4-triazole-5-carboxylate

EXAMPLE 11 A mixture of ethyl 1,2,4-triazole-3-carboxylate (1.41 g, 0.01 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (3.18 g, 0.01 mole) was melted and then 0.095 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 3 hours, while maintaining the temperature of the reaction mixture at 95+-5 C. And then, the reaction mixture was crystallized with 20 ml of methanol to give 3.27 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid ethyl ester (yield: 82%). NMR (CDCl3) delta (ppm): 1.43(t, 3H), 2.12(t, 9H), 4.00(m, 2H), 4.26(m, 1H), 4.48(m, 2H), 5.57(t, 1H), 5.77(q, 1H), 6.10(d, 1H), 8.50(s, 1H)

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; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1455-77-2, name is 3,5-Diamino-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 1455-77-2, COA of Formula: C2H5N5

A mixture of Hdatrz (19.8mg, 0.2mmol), CH3-H2ip (36.0mg, 0.2mmol) and Co(OAc)2¡¤4H2O (24.9mg, 0.1mmol) was dissolved in mixed H2O?CH3OH (v:v=1:1, 10.0mL) solution, and the initial pH value of the reactant mixture was adjusted to ca. 6 by slow addition of triethylamine with constant stirring. The resulting mixture was then transferred into a Teflon-lined stainless steel vessel (23.0mL) and heated at 160¡ãC for 96h under autogenous pressure. After the mixture was cooled to room temperature at a rate of 1.4¡ãCh?1, red block-shaped crystals suitable for X-ray analysis were obtained directly, washed with water and dried in air (Yield: 50percent, based on CoII salt). Anal. Calc. for C12H15CoN5O5: C, 39.14; H, 4.11; N, 19.02. Found: C, 39.14; H, 4.12; N, 19.05percent. IR (KBr pellet, cm?1): 3445 (s), 3333 (w), 3070 (w), 1670 (s), 1633 (s), 1546 (s), 1439 (s), 1370 (s), 1246 (w), 1083 (m), 1032 (m), 817 (w), 783 (m), 751 (w), 723 (m).

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

Reference:
Article; Zhao, Hong; Li, Hong-Xue; Liu, Zhong-Yi; Yang, En-Cui; Zhao, Xiao-Jun; Polyhedron; vol. 101; (2015); p. 29 – 36;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1001401-62-2, 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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of A-I (0.72 g, 3.8 mmol) and thionyl chloride (0.36 mL, 5.0 mmol) in toluene (7.0 mL) and a drop of DMF is heated to 60C for 2h, then cooled and concentrated. The residue isdissolved in dry DCM (5 mL) and added dropwise to a stirred mixture of B-I (0.65 g, 4.64 mmol)and TEA (1.44 mL, 10.3 mmol) in dry DCM (10 mL) at 0C. The reaction is stirred at RTfor2h.Water is added and the organic layer is separated, washed with citric acid (10% aq. solution)and with NaHCO3 (sat. aq. solution). The organic layer is dried and concentrated to provide 0.94g of C-4. ESI-MS: 275 [M+H], HPLC (Rt): 0.69 mm (method M)

The chemical industry reduces the impact on the environment during synthesis 2-(2H-1,2,3-Triazol-2-yl)benzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; (65 pag.)WO2017/178339; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3 -methyl- IH-1, 2,4-triazole (2.20 g, 26.4 mmol), l,5-difluoro-2- methoxy-4-nitrobenzene (5.00 g, 26.4 mmol), and potassium carbonate (3.65 g, 26.4 mmol) in anhydrous DMSO (50 mL) was heated at 80 0C for 24 h. The reaction mixture was allowed to cool to rt and was poured into 500 mL of water/10 mL brine solution. The aqueous mixture was extracted with EtOAc (2 x 250 mL). The combined organic extracts were washed with water (500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel column chromatography (50% EtOAc/hexane) to afford l-(5-fluoro-2-methoxy-4-nitrophenyl)-3- methyl-lH-l,2,4-triazole (1.24 g, 18 % yield). LC-MS (M+H)+ = 253.2. 1H NMR (SOO MHz, CDCl3) delta ppm 8.95 (s, 1 H) 8.00 (d, J=I 1.60 Hz, 1 H) 7.80 (d, J=6.10 Hz, 1 H) 4.09 (s, 3 H) 2.50 (s, 3 H).

The synthetic route of 3-Methyl-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, III, Lorin A.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2011/14535; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 13273-53-5,Some common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, 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 2-((4-chlorophenethyl)amino)-2-phenyl-l-(6-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-lH-indol-3-yl)ethan-l-one (0.06 g, 0.11 mmol), 4-bromo-l -methyl – 1H- 1,2, 3 -triazole (0.019 g, 0.11 mmol), and cesium carbonate (0.095 g, 0.29 mmol) in a mixture of 4:1 dioxane:water (5 ml) was degassed for 20 minutes with argon. S-Phos Pd precatalyst G3 (0.009 g, 0.01 mmol) was added and degassing was continued for another 10 minutes. The reaction mixture was heated in a sealed tube with microwave heating at 135 C for 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was treated with water (15 ml) and extracted with ethyl acetate (2 x 15 ml). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the title compound as solid (0.040 g, 74%) in racemic form.

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

Reference:
Patent; CONSTELLATION PHARMCEUTICALS, INC.; WILSON, Jonathan, E.; LEVELL, Julian, R.; (152 pag.)WO2019/161157; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 252742-72-6, These common heterocyclic compound, 252742-72-6, name is 3-(Chloromethyl)-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.

Benzylmercaptan (1.75 mL; 14.9 mmol) was dissolved in DMF (20 mL) and solid K2CO3 (2. 35 g; 17 mmol) was added. To the resulting slurry was added a solution of 5-(chloromethyl)-2,4-dihydro-3H-1, 2,4-triazol-3-one (2.0 g; 15 mmol) in DMF (12 mL), prepared by a literature procedure (C. J. Cowden et. al., Tetrahedron Letters 41 (2000) 8661-8664). The reaction mixture was stirred at room temperature for 20.5 h. Water (80 mL) was added and a thick slurry was formed. The solid product was collected by filtration and washed with water. The remaining filtrate and wash liquid still contained product and was extracted four times with EtOAc, and the organic phase was then washed with water (twice), brine (twice) and dried (Na2SO4). Evaporation of solvents gave another crop of crude product. The combined solid materials were suspended in toluene and evaporated to remove water residues. The crude product was then suspended in a boiling mixture of EtOAc/heptane (1: 4) and allowed to cool before the solid product was collected by filtration. The subtitle compound was obtained as a colourless solid (2.03 g; 61percent yield). APCI-MS m/z: 222.1 [MH+]. ‘H-NMR (DMSO-D6): 8 11.35 (1H, vbrs), 11.26 (1H, brs), 7.37-7. 21 (5H, m), 3.72 (2H, s), 3.36 (2H, s) ppm. ‘3C-NMR (DMSO-D6): 8 156.09, 144.75, 137.66, 128.83, 128.23, 126.79, 34.75, 25.80 ppm.

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; ASTRAZENECA AB; WO2005/95362; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1157938-97-0, 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 1157938-97-0 as follows.

(B) in a three neck reaction flask, propionitrile was added 4mol, 0.1mol catalyst (containing primary amine 0.05molC-9 cinchona alkaloids, 0.05mol formula and copper pigment base formula),Benzoic acid and 0.1mol 0.5LN, N- dimethylacetamide (the DMA), cooled to -10 , stirring the first solution containing 1mol product 0.3LN, N- dimethylacetamide solution, at -10 8 hours of reaction, TLC the reaction was complete, a solution of a concentration of 1mol / 0.3L L hydrochloric acid the reaction was quenched with 0.2L ethyl acetate three times, the combined organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, the resulting oil was treated with n-heptane / methylene chloride (1/1 by volume) was recrystallized, filtered and dried to give an off-white solid, i.e. a second product, yield 80%, dr is 97:3.;

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, Ke; (7 pag.)CN105777740; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics