Category: Triazoles

Adding some certain compound to certain chemical reactions, such as: 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, 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 27996-86-7. 27996-86-7

A mixture of alpha ionone (1.152 g, 1.23 ml, 6 mmol), 4-(1H-1,2,4-triazol-1-yl) benzaldehydes (0.865 g, 5 mmol), cetyltrimethyl ammonium bromide (0.070 g, 0.5 mmol), sodium hydroxide (0.600 g, 15 mmol) and water (25 ml) was stirred at room temperature for 24 h. Reaction progress was monitored by TLC and compound was extracted with ethyl acetate (2 ¡Á 50 ml). The combined organic extract was washed with water (2 ¡Á 50 ml), brine solution (50 ml), dried (Na2SO4) and the solvent was removed in vacuum. The crude product was purified by column chromatography (SiO2, 60-120 mesh). Elution with 10 % ethyl acetate in hexane furnished a pale yellow coloured solid (0.400g, 23%). Mp: 108-110OC; IR (KBr, cm-1): 2915, 1651 (C=O), 1598 (C=N); 1H NMR (CDCl3, 300 MHz): delta 0.88 (s, 3H), 0.95 (s, 3H), 1.22-1.29 (m, 1H), 1.43-1.52 (m, 1H), 1.60 (s, 3H), 2.07 (brs, 2H), 2.36 (d, J = 9 Hz, 1H), 5.53 (brs, 1H), 6.39 (d, J = 16 Hz, 1H), 6.85 (dd, J = 16, 9 Hz, 1H), 7.01 (d, J = 16 Hz, 1H), 7.63-7.74 (m, 5H), 8.11 (s, 1H), 8.60 (s, 1H); 13C NMR (CDCl3, 75 MHz): delta 22.92, 23.10, 26.90, 27.95, 31.25, 32.75, 54.67, 2¡Á120.13, 122.83, 125.72, 2¡Á129.72, 130.54, 131.93, 134.81, 137.99, 140.89, 141.16, 149.44, 152.81, 188.53; ESI-MS m/z: 348 [M+1]+; Analysis calculated for C22H25N3O: C, 76.05; H, 7.25; N, 12.09; Found: C, 76.05; H, 7.29; N, 12.03.

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 4-[1,2,4]Triazol-1-yl-benzaldehyde.

Reference:
Article; Suryawanshi; Tiwari, Avinash; Kumar, Santosh; Shivahare, Rahul; Mittal, Monika; Kant, Padam; Gupta, Suman; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2925 – 2928;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

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

Reference:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
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. 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 27996-86-7

Step 1. (?)-3-(4-(lH-l,2,4-triazol-l-yl)phenyl)-l-(3,5-dichlorophenyl)prop-2-en-l- one: To a solution of l-(3,5-dichlorophenyl)ethanone (0.5 g, 2.6 mmol) in ethanol (20 mL) was added 4-(lH-l,2,4-triazol-l-yl)benzaldehyde (0.46 g, 2.65 mmol) and the reaction was cooled to 0 C. Sodium hydroxide (0.22 g, 5.29 mmol) in water (10 mL) was then added and the reaction was allowed to stir for 2 h at 0 C. The reaction was extracted with EtOAc and the combined organic layers were dried over Na2S04 and concentrated under reduced pressure to afford the title compound (0.149 g, 17%): ); ESIMS m/z 430.05 ([M+H]+) 344.08

The synthetic route of 27996-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., 16681-70-2

[0725] lH-1,2,3-triazole-5-carboxylic acid (2.3 mg, 20f.tmol) was combined with HATU (5.9 mg, 15 flillOI) in DMF(0.5 mL) and stirred for lOminutes; DIPEA (1 eq.)was addedand the mixture was stirred for 1 minute. Compound 2 (10.0mg, 22 f.tmol) was dissolved in DMF (1 mL) and DIPEA (11.6f.LL, 66 flillOI) was added, followed by addition of the activatedacid solution. The mixture was stirred for 30 minutes and thenconcentrated in vacuo to yield Compound 3.

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; 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

1257633-67-2, A common compound: 1257633-67-2, name is 1-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole, 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.

To a 50-mL round bottom flask was added a solution of 1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole (1.28 g, 5.63 mmol) in dichloromethane (6.0 mL), followed by addition of water (3.0 mL) and trifluoroacetic acid (1.0 mL) The reaction mixture was stirred vigorously under nitrogen for 3 h and then was diluted with EtOAc (100 mL), washed with sat aq NaHCO3 (3¡Á40 mL) and brine (40 mL). The combined organic phases were dried over anhydrous MgSO4, filtered. Solvent was removed and the residue was used in the next step without purification. 1H NMR complies with the reported value.

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-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCACATION; Zeng, Dexing; (26 pag.)US2017/297008; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

27808-16-8, name is 4-Methyl-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. 27808-16-8

N-Bromosuccinimide (5.89 g, 33.1 mmol) was added to a solution of 4-methyl-1H-1,2,3-triazole (2.50 g, 30.1 mmol) in chloroform (30 mL), and the reaction mixture was stirred for 16 hours at room temperature (15 C.). It was then diluted with dichloromethane (100 mL), washed with water (2¡Á100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to provide the product as a white solid (4.9 g), which was used directly in the next step.

Statistics shows that 27808-16-8 is playing an increasingly important role. we look forward to future research findings about 4-Methyl-1H-1,2,3-triazole.

Reference:
Patent; Pfizer Inc.; Galatsis, Paul; Henderson, Jaclyn Louise; Kormos, Bethany Lyn; Kurumbail, Ravi G.; Reese, Matthew Richard; Stepan, Antonia Friederike; Verhoest, Patrick Robert; Wager, Travis T.; Pettersson, Martin Youngjin; Garnsey, Michelle Renee; (150 pag.)US2017/73343; (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. 28938-17-2 name is 4,5-Dibromo-2-methyl-2H-1,2,3-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. 28938-17-2

4-bromo-2-methyl-2H-l,2,3-triazole. n-Butyllithium (8.3 mL) was added dropwise to a solution of 4,5-dibromo-2-methyl-2H-l,2,3-triazole (2.0 g, 8.37 mmol) in tetrahydrofuran (50 mL) under -78C, Once addition was completed, the mixture was stirred for another 30 minutes at -78C. The reaction was quenched with water, extracted with ethyl acetate (50 mL x 3), washed by brine (30 mL x 3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated in vacuo to afford 4-bromo-2-methyl-2H- 1,2,3- triazole.

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

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

1186050-58-7, 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. 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (S)-2,7-dimethyl-3-(3,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine (15 mg, 53.3 mumol) (Intermediate 40) in CH2Cl2 (0.48 mL) was added 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (prepared according to methods described in Pat. Pub. No. WO2012145581, Oct. 26, 2012) (12.2 mg, 58.7 mumol), HATU (26.4 mg, 69.3 mumol), and N,N-diisopropylethylamine (27.6 muL, 0.16 mmol). After stirring at room temperature for 30 min, the mixture was concentrated in vacuo and purified by preparative HPLC (XBridge C18 column (5 mum, 100*4.6 mm), mobile phase of 5-95% ACN in 20 mM aqueous NH4OH) to afford the title compound as a white powder (21 mg, 84% yield). MS (ESI): mass calcd. for C23H18F4N6O, 470.1; m/z found, 471.2 [M+H]+. 1H NMR (600 MHz, DMSO-d6) delta 8.19-8.05 (m, 1.62H), 7.93-7.90 (m, 0.40H), 7.87-7.83 (m, 0.91H), 7.74-7.66 (m, 1H), 7.59-7.38 (m, 3H), 5.59-5.49 (m, 0.74H), 4.73-4.62 (m, 0.28H), 4.57-4.51 (m, 0.17H), 3.81 (s, 2.26H), 3.76 (s, 0.22H), 3.70 (s, 0.52H), 3.64-3.52 (m, 0.72H), 3.38-3.17 (m, 0.73H), 3.07-3.00 (m, 0.22H), 2.84-2.76 (m, 0.15H), 2.71-2.60 (m, 0.63H), 2.45-2.22 (m, 1.47H), 1.47 (d, J=6.7 Hz, 2.28H), 1.35 (d, J=6.8 Hz, 0.6H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Chen, Gang; Huang, Chaofeng; Laforteza, Brian Ngo; Ravula, Suchitra; Southgate, Emma Helen; Zhang, Wei; US2020/102303; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

162848-16-0, 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. 162848-16-0, name is 4-[1,2,4]Triazol-1-yl-benzoic acid, A new synthetic method of this compound is introduced below.

At 40 C 1-hydroxybenzotriazole hydrate (0.13 g, 0.99 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.19 g, 0.99 mmol) were added to astirred solution of 4-(1/-/-1,2,4 triazol-1yl)benzoic acid (0.16 g, 0.82 mmol) in N,N-dimethylformamide (5 mL). After 30 minutes methyl-phenyl-carbamic acid 5-amino-pyridin-2-yl ester (0.20 g, 0.82 mmol) and A/-ethyldiisopropylamine (0.17 mL, 0.99 mmol) were addedand stirring was continued overnight at 40 C. The solvent was evaporated in vacuo. A smallportion of the crude product (around 100 mg) was purified by preparative HPLC yielding thetitle compound (10 mg. 1% yield) as a white solid.1H NMR (400 MHz, DMSO-c/6): 5- 7.25 (d, 1H), 7.30 (m, 1H), 7.45 (m, 4H), 8.07 (d,2H), 8.18 (d, 2H), 8.28 (dd, 1H), 8.32 (s, 1H), 8.69 (d, 1H), 9.45 (s, 1H), 10.62 (s, 1H); HPLC-MS (Method A): m/z = 415 (M+H)+; Rt = 3.13 min.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NOVO NORDISK A/S; WO2004/111031; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, 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. 1186050-58-7

A mixture of [4-(Hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-6-methoxy-pyrimidin-2-yl]- dimethyl-amine (60.0 mg, 0.23 mmol), 2-fluoro-6-[1 ,2,3]triazol-2-yl-benzoic acid (52.0 mg, 0.25 mmol), HATU (130.0 mg, 0.34 mmol) and DIPEA (0.12 mL, 0.68 mmol) was stirred into DMF (4.0 mL) at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate (60.0 mL) and washed with water (2 X 100 mL). The organic phase was dried (Na2SO4), filtered and concentrated to dryness to yield crude title compound (354.0 mg, 343 %). The crude product was purified using Agilent HPLC (Basic system) to yield pure title compound (84.0 mg, 81 .5 %). MS (ESI) mass calcd. for C22H25FN8O2,452.49; m/z found 453.3 [M+H]+. 1 H NMR (CDCI3): 7.88-7.79 (m, 2H), 7.72 (d, J = 6.7, 1 H), 7.54-7.41 (m, 1 H), 7.19-7.08 (m, 1 H), 5.02-4.92 (m, 1 H), 3.96-3.86 (m, 1 H), 3.87-3.83 (m, 3H), 3.81 -3.50 (m, 5H), 3.43-3.19 (m, 2H), 3.15-3.09 (m, 6H)), 3.09-2.91 (m, 2H).

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 1186050-58-7.

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