Triazoles

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

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

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

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

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

13273-53-5, 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. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

In a microwave tube to a mixture of 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indolin-2-one (100 mg, 395 imol, Eq: 1.00, cf. Example 70 step c) and 4-bromo-1-methyl-1H-1,2,3-triazole (76.7 mg, 474 imol, Eq: 1.2) was added acetonitrile (3 ml). The solvent was degassed by bubbling nitrogen through the suspension for 10 minutes. Then was added at 22 C N,N?5 dimethylethylenediamine (6.96 mg, 8.5 jil, 79.0 imol, Eq: 0.2) followed by potassium carbonate(136 mg, 987 imol, Eq: 2.5) and copper (I) iodide (7.52 mg, 39.5 imol, Eq: 0.1). The tube was inerted, sealed and the mixture was heated in microwave at 170C for 30 minutes.The mixture was treated with 2 ml of water and extracted with ethyl acetate (2 x 2 ml). The organic layers were dried, filtered and concentrated in vacuo.The residue was purified by chromatography on silica gel to give the desired compound as a white solid (8 mg, 6%). MS (mlz) = 335.2 [M + H].

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, 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 4922-98-9. 4922-98-9

Example 11; Part A; A reaction mixture of 3-phenyl-1 H-1 ,2,4-tpiazol-5-amiotane (160 mg, 1 mmol) and dimethyl but-2-ynediotaoate (123 mul_, 1 mmol) in methanol (2 ml_) was stirred at room temperature for overnight Purification using reverse phase HPLC gave compound 11-1 as a solid after lyophilization HPLC-MS RT= 3 08 mm, mass calculated for formula Ci3H10N4O3270 08, observed LCMS m/z 271 28 (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 5-Phenyl-1H-1,2,4-triazol-3-amine.

Reference:
Patent; SCHERING CORPORATION; SHIPPS, JR., Gerald, W.; CHENG, Cliff, C.; HUANG, Xiaohua; ACHAB, Abdelghani, Abe; ORTH, Peter; VOIGT, Johannes, H.; SOUCY, Kyle, Ann; WO2010/56631; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 64922-04-9, name is Ethyl 1H-1,2,4-triazole-5-carboxylate, molecular formula is C5H7N3O2, 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. 64922-04-9

Example 1.10: Preparation of l-ethyl-lH-[l,2,,4~|triazole~3-carboxyric acid methyl ester and 1 -ethyl- IH-[1, 2,4]triazole-5-carboxylic acid methyl esterTo a suspension of IH-[1, 2,4]-triazole-3-carboxylic acid methyl ester (25 g, commercially available) in dry lambdazetaN-dimethylformamide (200 ml) at O0C under an atmosphere of nitrogen was added in portions sodium hydride (60% by weight dispersion in mineral oil) (8.66 g). On complete addition, the mixture was stirred for 1 hour at ambient temperature then re-cooled to O0C and ethyl iodide (15.5 ml) was added. The reaction mixture was stirred for 1 hour, stored for 18 hours then treated with aqueous ammonium chloride (IM) and concentrated to give a yellow oil. The oil was dissolved in chloroform (300 ml), washed with water (100 ml), dried over magnesium sulfate and concentrated. The oil that remained was washed with hexane and then triturated with diethyl ether to give a mixture of l-ethyl-lH-[l,2,4]triazole-3-carboxylic acid methyl ester and 1 -ethyl- IH-[1, 2,4]triazole-5-carboxylic acid methyl ester which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64922-04-9, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2008/74991; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

23579-79-5, A common compound: 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-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.

A mixture of 17.5 g (0.073 mol) of triazole 2a and 36.5 mL (0.73 mol) of 98 % hydrazine hydrate in 150 mL of propan-2-ol was refluxed for 5.5 h with stirring. The mixture was cooled, the precipitate was filtered off, and the filtrate was evaporated to a volume of 15 mL to isolate an additional amount of the product which was combined with the main portion and recrystallized from toluene. Yield 11.6 g (83 %), mp 196-197 C. IR spectrum, nu, cm-1: 3325 (NH), 3256, 2924,1634 (NH), 1582, 1521, 1456, 1437, 1429, 1331, 1294, 1246, 1227, 1132, 1024, 999, 947, 866, 731, 681, 608, 567, 557. 1H NMR spectrum, delta, ppm: 3.51 s (3H,CH3), 4.52 br.s (2H, NH2, overlapped by the signal of water present in the solvent), 7.84 s (1H, NH). 13C NMR spectrum, deltaC, ppm: 34.3 (CH3), 135.5 (C3),159.5 (C5). Mass spectrum, m/z (Irel, %): 193 (61.3) [M]+, 191 (64.2) [M]+, 178 (4.8), 177 (8.2), 176 (8.2), 175 (10.0), 174 (2.9), 164 (3.1), 163 (4.1), 161 (9.1), 159 (8.2), 136 (5.3), 135 (9.4), 134 (6.3), 133 (11.4), 112 (70.4), 108 (16.0), 106 (16.1), 95 (13.0), 83 (43.0), 82 (47.8), 81 (8.6), 80 (5.7), 78 (6.9), 68 (5.9), 56 (7.6), 55 (18.1), 53 (30.6), 43 (100), 42 (32.7), 41 (7.9), 40 (7.3), 31 (18.6), 30 (37.6), 29 (18.8), 28 (11.8), 27 (7.5), 17 (5.7), 16 (8.9), 15 (39.4). Found,%: C 19.07; H 3.11; N 36.87. C3H6BrN5. Calculated, %: C 18.77; H 3.15; N 36.47. M 192.02.

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

Reference:
Article; Tolstyakov; Russian Journal of Organic Chemistry; vol. 54; 10; (2018); p. 1537 – 1547; Zh. Org. Khim.; vol. 54; 10; (2018); p. 1525 – 1534,10;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

15988-11-1,Some common heterocyclic compound, 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, molecular formula is C8H7N3O2, 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: Dimedone (0.14 g, 1 mmol), benzaldehyde (0.1 g, 1 mmol), and 4-phenylurazole (0.177 g, 1 mmol) were mixed with PEG-SO3H (0.6 g, 0.1 mmol) and the obtained mixture was stirred magnetically at 80 C for 40 min. After the completion of the reaction warm water (20 mL) was added and the mixture stirred for about 5 min. The insoluble crude product was filtered and recrystallized from EtOH/H2O 4:1 and the pure product was obtained (0.352 g, 91%). In order to recover the catalyst, the filtrate was dried under reduced pressure and recovered catalyst was washed with diethyl ether and reused after drying under reduced pressure. The equivalent procedure was used for the synthesis of triazolo[1,2-a]indazole-tetraones.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15988-11-1, its application will become more common.

Reference:
Article; Hasaninejad, Alireza; Zare, Abdolkarim; Shekouhy, Mohsen; Tetrahedron; vol. 67; 2; (2011); p. 390 – 400;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics