Category: Triazoles

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

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

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

These common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-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. Application In Synthesis of 3,5-Diamino-1,2,4-triazole

Example 12-Amino-6- [(3-chlorophenyl)methyl] -5-cyclopropyl-4H- [ 1 ,2,4] triazolo [5,1- b] pyrimidin-7-one3,5-Diamino-l,2,4-triazole (141 mg, 1.42 mmol) was added to ethyl 2-[(3- chlorophenyl)methyl]-3-cyclopropyl-3-oxo-propanoate (200 mg, 0.71 mmol) and 1-butyl- 3-methylimidazolium hexafluorophosphate (1 mL, 4.25 mmol) in a microwave tube at room temperature. The open tube was then placed in a fitted aluminium block preheated to 200 ¡ãC and magnetically stirred for 20 minutes with the formation of a white precipitate. After cooling the mixture was added to DCM (30 mL), water (10 mL) and citric acid (10percent aqueous solution, 1 mL) and stirred for 20 minutes. The layers were separated using a hydrophobic membrane filter and the organic layer was evaporated. The remaining aqueous layer was filtered and the solid collected. The crude product was dissolved and purified by preparative HPLC (Waters XTerra CI 8 column, 5mu silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1percent NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (110 mg, 48.9 percent) as a white solid.1H NMR (700.03 MHz, DMSO-d6) delta 0.85-0.90 (2H, m), 0.93-0.98 (2H, m), 2.06-2.10 (1H, m), 3.98 (2H, s), 6.16 (2H, br s), 7.15-7.21 (2H, m), 7.27-7.29 (2H, m), 12.17 (1H, br s) m/z (ES) (M+H)+ = 316.

The synthetic route of 3,5-Diamino-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BENGTSSON, Boel, Ase; BLACKABY, Wesley; CUMMING, John; FAULL, Alan, Wellington; LARSSON, Joakim; NASH, Ian, Alun; OLDHAM, Keith; PAPE, Andrew; WO2011/114148; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-36-8, The chemical industry reduces the impact on the environment during synthesis 288-36-8, name is 1H-1,2,3-Triazole, I believe this compound will play a more active role in future production and life.

To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol) , cesium carbonate (89.26 g, 274 mmol) , and CuI (5.27 g, 27.4 mmol) in DMF (200 mL) was added N, N? -dimethylcyclohexane-1, 2-diamine (3.7 mL, 23.3 mmol) and 1H-1, 2, 3-triazole (18.92 g, 274 mmol) . The resulting mixture was stirred at 110 overnight, cooled, concentrated in vacuo, and diluted with water (150 mL) . The aqueous layer was washed with EtOAc (300 mL x 3) . The aqueous layer was acidified with 2 N HCl and extracted with EtOAc (300 mL x 4) . The combined organic layers were washed with brine (150 mL x 3) , dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (petroleum ether: EtOAc100: 15: 1) to provide the title compound as a solid. LRMS m/z (M+H) 208.0 found, 208.0 required.

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, 1H-1,2,3-Triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; (59 pag.)WO2016/101118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic 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. Quality Control of 1H-[1,2,3]Triazole-4-carboxylic acid

[0784] 1H-1,2,3-triazole-5-carboxylic acid (3.4 mg, 30f.tmol) was combined with HATU (11 mg, 30 f.tmol) in DMF(0.3 mL) stirred at room temperature for 10 minutes; DIPEA(1 eq.) was added and the mixture was stirred for 1 minute.Compound 2 (10 mg, 30 f.tmol) was dissolved in DMF (0.5mL) and DIPEA (5.2 f.LL, 30 f.tmol) was added, followed byaddition of the activated acid solution. The mixture wasstirred at room temperature for 30 minutes, after which timeLCMS indicated desired product formation. Half of the crudeproduct was purified using reverse phase chromatography toyield Compound a as a TFA salt (1 mg). MS m/z [M+Htcalc’d for C26H31CIFN50 4 , 532.21. found 532. Half of thecrude product was carried to the next step without furtherpurification.

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 16681-65-5,Some common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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 stirred solution of 1 -methyl- 1 H- 1,2,3-triazole (0.5 g, 6.0 mmol) in anhydrous tetrahydrofuran (50 mL) at -78 C under an atmosphere of nitrogen was added n-butyllithium (2.5M solution in hexanes, 2.6 mL, 6.6 mmol) dropwise over ten minutes. On complete addition the reaction was allowed to warm to -30 C and stirred for 2 h. A solution of chlorotrimethylstannane (1.3 g, 6.6 mmol) in tetrahydrofuran (2 mL) was added dropwise over 10 minutes then the reaction mixture was allowed to warm to room temperature over 2 h. The reaction was quenched by the addition of saturated ammonium chloride solution (5 mL) then diluted with water (20 mL). The solvent was evaporated in vacuo and the aqueous phase extracted with ethyl acetate (2 x 30 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated to afford a pale yellow oil (1.4 g, 90%). 1H NMR (DMSO- D6,400MHz): 7.61 (s, 1H), 4.04 (s, 3H), 0.40 (s, 9H).

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-1,2,3-triazole, its application will become more common.

Reference:
Patent; GENENTECH, INC.; WO2009/151598; (2009); 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Methyl-1H-1,2,4-triazole

A solution of compound 1 (30 g, 0.13 mol) in THF (1.5 L) was cooled to 78 C. Vinylmagnesium in THF (508 mL, 1N, 0.51 mol) was added dropwise to the above solution and the temperature was maintained below 40 C. The mixture was stirred for 3 h at 78 C before being quenched with saturated aqueous NH4Cl solution. The layers were separated, the aqueous layer was extracted with EtOAc (3 500 mL), and the combined organic layer was washed with brine and concentrated.The crude product was purified by silica gel column chromatography to obtain compound 2 (5 g,17%). Compound 2 (4.0 g, 17.2 mmol) was dissolved in freshly prepared NaOMe (20 mL). CuI(3.2 g, 17.2 mmol) was added and the mixture was microwave-irradiated at 110 C and stirred for3 h. After reaction completion, EtOAc and H2O were added, then the suspension was filtered andthe filtrate was separated. The organic layer was concentrated to give crude product, which waspurified by column chromatography to give compound 3 (1.8 g, 45%). A mixture of compound 3(0.7 g, 3.8 mmol), 3-methyl-1,2,4-triazole (6.4 g, 76.8 mmol), copper powder (0.49 g, 7.68 mmol), and KOH (0.43 g, 7.68 mmol) was heated to melt at 170-175 C while being protected by N2 atmosphere. After consumption of the starting material, EtOAc and H2O were added to the mixture, and the suspension was filtered and the filtrate was collected. The organic layer was concentrated to give the crude product, which was purified by column chromatography to give compound 4 (0.23 g, 26%).A solution of compound 4 (0.23 g, 1 mmol) in THF (12 mL) was cooled to 10 C, and EtMgBr (0.47 g,3.5 mmol) was added dropwise at 10 C, followed by the addition of pyridine (0.3 mL). The slurrywas cooled to 45 C, and the ethyl 2-chloro-2-oxoacetate (0.55 g, 4 mmol) was added dropwise at 45 C. The temperature was allowed to rise to 10 C and the mixture was stirred for 1h. Afterreaction completion, the mixture was quenched with IPA (2 mL) and H2O (20 mL). The mixture wasextracted with EtOAc, and the organic layer was washed with brine and concentrated to the givecrude product which was purified by column chromatography to give compound 5 (0.17 g, 52%).Compound 5 (0.17 g, 0.52 mmol) was dissolved in MeOH (5 mL). NaOH (0.041 g, 1.03 mmol) and H2O(2 mL) were added and the mixture was stirred at 25 C for 6 h. HCl (1N) was added to adjust the pH to 6, and the mixture was concentrated to give compound 6 (0.29 g) as crude product.

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; Meuser, Megan E.; Murphy, Michael B.; Rashad, Adel A.; Cocklin, Simon; Molecules; vol. 23; 8; (2018);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic 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 16681-70-2, Quality Control of 1H-[1,2,3]Triazole-4-carboxylic acid

[0769] 3H-1,2,3-triazole-5-carboxylic acid (2.5 mg, 22f.tmol) was combined with HATU (8.4 mg, 22 flillOI) in DMF(0.3 mL) and stirred for 10 minutes; Et3N (1 eq.) was addedand the mixture was stirred for 1 minute. Compound 2 (22f.tmol) was dissolved in DMF (0.5 mL) and Et3N (3.1 f.LL, 22f.tmol) was added, followed by addition of the activated acidsolution. The mixture was stirred for 30 minutes, concentrated,and purified by preparative HPLC to yield Compounda (8 mg) as a TFA salt. MS m/z [M+Ht calc’d forC26H29CIFN50 3 , 514.19. found 514.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-[1,2,3]Triazole-4-carboxylic acid, and friends who are interested can also refer to it.

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

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. SDS of cas: 61-82-5

General procedure: A mixture of 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1.0 mmol), arylaldehyde (1.0 mmol), dimedone (1.0 mmol), and 15 mol % p-TsOH.H2O was stirred in 5 cm3 acetonitrile as solvent at 40-50 C for the appropriate time (Table 3). The progress of the reaction was monitored by TLC. After completion of the reaction, a thick precipitate was obtained. The solid product was filtered off and washed with acetonitrile and subsequently dried in air. The pure product was characterized by conventional spectroscopic methods.

The synthetic route of 1H-1,2,4-Triazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Monatshefte fur Chemie; vol. 145; 12; (2014); p. 1967 – 1973;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics