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. 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

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

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 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, 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

Adding a certain compound to certain chemical reactions, such as: 288-88-0, name is 1H-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 288-88-0, name: 1H-1,2,4-Triazole

0.69 g (10 mmol) of 1,2,4-triazole, 2.07 g (15 mmol) of potassium carbonate, 1.49 g(12mmol) of p-fluorobenzaldehyde, and dissolved in 50 mL of N,N-dimethylformamide. It was placedina 100 mL three-neckedflaskequipped with a thermometer and a stirring device.The reaction was carried out under constant temperature stirring at 100 C for 16 h, cooled to room temperature, extracted, suction filtered, separated by column chromatography, washed with warm water, recrystallized from anhydrous ethanol, and dried under vacuum at 50 C for 8 h to obtain 1,2,4-triazole benzaldehyde.

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-1,2,4-Triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qilu University of Technology; Duan Hongdong; Zhong Wenxia; (12 pag.)CN109867683; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 930-33-6, 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. 930-33-6, name is 1H-1,2,4-Triazol-3(2H)-one belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 5 3-[6-Bromo-2-fluoro-3-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl)-phenoxy]-5-chloro-benzonitrile (I-8) Ar=3-chloro-5-cyano-phenyl A solution of A-2d (200 mg, 0.477 mmol), 2,4-dihydro-[1,2,4]triazol-3-one (10, CASRN 930-33-6, 0.040 g, 1.0 eq), K2CO3 (0.13 g, 2.0 eq), and KI (0.008 g, 0.1 eq) and MeCN (1.5 mL) was heated to 85 C. for 2 h and then cooled to RT. The reaction mixture was diluted with 10% MeOH/DCM, and washed sequentially with water and brine. The organic extracts were evaporated and the crude product purified by SiO2 chromatography eluding with a MeOH/DCM gradient (3-10% MeOH) to afford 0.020 g (10%) of 1-8 as a white solid.

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

Reference:
Patent; Roche Palo Alto LLC; US2009/12034; (2009); 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. category: Triazoles

4′-nitroacetophenone was used in place of 2-acetylthiophene in Reference Example 001 and heated to reflux in xylene in the presence of N,N-dimethylformamide diethyl acetal as in Reference Example 001, and 3-dimethylamino-1-(4-nitrophenyl)propenone (quantitative) was obtained, which was subsequently reacted with 3,5-diamino-1,2,4-triazole in xylene in the presence of 10-camphor sulfonic acid and the title compound was obtained (yield 82percent).

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; NIPPON KAYAKU KABUSHIKI KAISHA; EP1674454; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 41253-21-8, 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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

[Step 1] Synthesis of ethyl 2-methyl-2-(1H-1,2,4-triazol-1-yl)propanoate: At room temperature, cesium carbonate (5.0 g, 15 mmol) and sodium 1,2,4-triazol-1-ide (0.58 g, 6.2 mmol) were added to a solution of ethyl 2-bromo-2-methylpropanoate (1.0 g, 5.1 mmol) in DMF (25 mL). The resulting reaction solution was stirred at 50C for 24 hours, and then concentrated under reduced pressure. Water was added to the obtained crude product, and extraction with chloroform was carried out. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, followed by purifying the obtained crude product by silica gel column chromatography (eluent, hexane:ethyl acetate = 7:3 ? 4:6), to obtain 0.84 g (89%) of ethyl 2-methyl-2-(1H-1,2,4-triazol-1-yl)propanoate (hereinafter referred to as Reference Example Compound 40).

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, Sodium 1,2,4-triazol-1-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Toray Industries, Inc.; NISHIMURA, Yutaka; KATO, Yuko; HAYASHI, Shinnosuke; YAMAZAKI, Aiko; YAMAMOTO, Masashi; ASAOKA, Yoshiji; YAMADA, Masateru; YAMADA, Naohiro; EP2832724; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 67545-00-0, name is 4-Amino-1-methyl-1,2,3-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 67545-00-0, name: 4-Amino-1-methyl-1,2,3-triazole

In a microwave vial (35 mL) was added S-129 (0.78 g, 1.82 mmol), amine 11 (0.18 g, 1.82 mmol), Cs2CO3(1.18 g, 3.64 mmol.) and Dioxane (25 mL). The Argon was purged through septum and the reaction mixture was degassed for about 5 min. To this mixture was added Xantphos (103 mg, 0.2 mmol) followed by Pd2(dba)3(162 mg, 0.2 mmol) and purged with Argon again for 5 min. Vial was sealed with the septum and irradiated at 140 C for 3 h. After filtration, the obtained crude was chromatographed (Biotage, 25 g, eluent: DMC-EtOAc: 10-50%) to afford S-6-1 (390 mg, 44%).1H NMR (400 MHz, DMSO-d6): delta 9.61 (bs, 1H), 7.99 (d, J = 7.8 Hz, 1H), 7.46- 7.10 (m, 10H), 6.87 (d, J = 3.9 Hz, 1H), 5.39 (m, 1H), 4.02 (s, 3H), 3.35- 3.23 (m, 2H), 2.32 (s, 3H), 2.23 (m, 2H). FABMS (M+H) calculated for was 489.1815 found 489.1813. LCMS 99%, tR= 7.37 minutes.

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; SOUTHERN RESEARCH INSTITUTE; AUGELLI-SZAFRAN, Corinne, E.; SUTO, Mark; GALEMMO, Robert; MOUKHA-CHAFIQ, Omar; GUPTA, Vandana; ANANTHAN, Subramaniam; (254 pag.)WO2017/106771; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics