Category: Triazoles

Application of 15294-81-2,Some common heterocyclic compound, 15294-81-2, name is 4,5-Dibromo-1H-1,2,3-triazole, molecular formula is C2HBr2N3, 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.

Example 121: Preparation of 4,5-dibromo-l-methyl-lH-[l,2,3″|triazole and 4,5-dibromo- 2-methyl-2H-[l .2.31triazole(A) (B) To a solution of 4,5-dibromo- IH-[1, 2,3]triazole (2.26 g, 10 mmol) (Example 120) and triethyl amine (1.5 ml, 10 mmol) in dichloromethane (50 ml), was added methyl iodide (625 mul, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. More triethyl amine (0.75 ml, 5 mmol) and more methyl iodide (312 mul, 5 mmol) were added and the mixture was stirred for 3 hours. The reaction mixture was quenched by addition of aqueous ammonium chloride (saturated) (15 ml). The phases were separated and the organic phase was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: 10-30% ethyl acetate in hexane) to give 4,5-dibromo-2-methyl-2H-[l,2,3]triazole (isomer B) (625 mg, 26% yield) and 4,5-dibromo- 1 -methyl- IH-[1, 2,3]triazole (isomer A) (825 mg, 34% yield).Isomer A 1H-NMR (400 MHz, CDCl3): 4.09 (s, 3H, Me) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 4.18 (s, 3H, Me) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,5-Dibromo-1H-1,2,3-triazole, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2007/96576; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-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. category: Triazoles

Synthesis of 1-fluoro-2-methoxy-4-nitrobenzene (1023) To a stirred solution of 1-fluoro-2-methoxy-4-nitrobenzene (2.5 g, 14.60 mmol) in DMF (25 mL) under an argon atmosphere were added potassium carbonate (4 g, 29.20 mmol) and 3-methyl-1H-1,2,4-triazole (1.2 g, 14.60 mmol) at room temperature. The reaction mixture was stirred at 85 C. for 16 h in a sealed tube. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2¡Á50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 15-25% EtOAc:hexane to afford 1-fluoro-2-methoxy-4-nitrobenzene (1.2 g, 35%) as an off-white solid. 1H-NMR (CDCl3, 400 MHz): delta 8.87 (s, 1H), 8.10 (d, 1H), 8.00-7.97 (m, 2H), 4.10 (s, 3H), 2.50 (s, 3H); LCMS: 234.9 (M+1); (column; Ascentis Express C-18 (50¡Á3.0 mm, 2.7 mum); RT 2.02 min. 0.025% Aq TFA+5% ACN: ACN+5% 0.025% Aq TFA; 1.2 mL/min); TLC: 30% EtOAc:hexane (Rf: 0.2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7170-01-6, its application will become more common.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 4928-87-4

General procedure: A mixture of amine I (1 equiv), desired carboxylic acid (1 equiv), triethylamine (Et3N) (3 equiv), and 2-(lH-benzotriazo1elyl),l,3,3tetranethyluronium hexafluoro-phosphate (HBTU) (1.5 equiv) in DMF (0.25 H) was stirred at room temperature until the reaction was complete by TLC or LCMS. The mixture was diluted with H,O andextracted with EtOAc. The combined organic extracts were washed with H,O, brine, dried over Ha,804, filtered, and concentrated under reduced pressure. The resulting residue was purified by either normal phase silica gel column chromatography (typical eluents included either a mixture of or hexanes and EtOAc or a mixture ofCH,Cl, and a 90:9:1 mixture of CH,Cl,/CH,OH/concentrated NH,OH) or C-18 reversed phase column chromatography (typical eluents included CH,CN and H,O( to afford the desired carboxamide It. The product structure was verified by ?H NMR and by mass analysis.

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; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; PETRUKHIN, Konstantin; CIOFFI, Christopher; JOHNSON, Graham; DOBRI, Nicoleta; FREEMAN, Emily; CHEN, Ping; CONLON, Michael; ZHU, Lei; WO2014/151936; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 13273-53-5, The chemical industry reduces the impact on the environment during synthesis 13273-53-5, name is 4-Bromo-1-methyl-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-morpholino-N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-3-yl)acetamide (LXV) (675.4 mg, 1.7 mmol), 4-bromo-1-methyl-1H-1,2,3-triazole (LXVI) (0.55 g, 3.4 mmol) and SPhos Pd G4 (135 mg, 0.17 mmol) in dioxane (10 mL) was added 2 N aqueous K3PO4 (1.7 mL, 3.4 mmol). N2 gas was bubbled into the mixture for 10 min and then heated to 90 C. for 24 h. The reaction mixture was partitioned between EtOAc and aqueous saturated NaHCO3. Insoluble solids were removed by filtration and the organic layer separated and washed with water and brine. The organic layer was separated, dried (MgSO4) and concentration to dryness under vacuum. The crude was then combined with the insoluble solid, dissolved in a mixture of chloroform/MeOH, absorbed on silica gel and was purified by column chromatography (0%?70% CHCl3/10% 7N NH3 MeOH in CHCl3) to give N-(6-(1-Methyl-1H-1,2,3-triazol-4-yl)isoquinolin-3-yl)-2-morpholinoacetamide 11 as a brown solid (170.0 mg, 0.482 mmol, 28.4% yield). 1H NMR (499 MHz, DMSO-d6) delta ppm 2.55-2.61 (4H, m), 3.25 (2H, s), 3.63-3.69 (4H, m), 4.14 (3H, s), 8.04 (1H, dd, J=8.51, 1.65 Hz), 8.13 (1H, d, J=8.78 Hz), 8.33 (1H, s), 8.50 (1H, s), 8.74 (1H, s), 9.13 (1H, s), 10.07 (1H, s); ESIMS found for C18H20N6O2 m/z 353.2 (M+1).

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, 4-Bromo-1-methyl-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mittapalli, Gopi Kumar; Chiruta, Chandramouli; Hofilena, Brian Joseph; Mak, Chi Ching; Eastman, Brian Walter; Bollu, Venkataiah; (158 pag.)US2019/119263; (2019); 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. 162848-16-0, name is 4-[1,2,4]Triazol-1-yl-benzoic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H7N3O2

Synthesis of N-[2,6-dibromo-4-(l,l,l,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4- (1H-1,2,4- triazol-l-yl)benzamide (Compound No. 1-78).[0147] Step 1 – 1 : Synthesis of 4-( 1 H- 1 ,2,4-triazol- 1 -yl)benzoyl chloride[0148] 4-(lH-l,2,4-triazol-l-yl)benzoic acid (0.90 g) was suspended in toluene. To the suspension, thionyl chloride (5.7 g) and an catalytic amount of N,N-dimethylformamide (2 to 3 drops) were added and the mixture was refluxed under heating for 4 hours. After adjusting the reaction solution to room temperature, the solvent was distilled off under reduced pressure to obtain4-(lH-l,2,4-triazol-l-yl)-benzoyl chloride as a crude product (0.95 g). Without further purification, the crude product was used for the next reaction.

The synthetic route of 162848-16-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; MIHARA, Jun; ARAKI , Koichi; MORI , Takuma; MURATA , Tetsuya; YONETA, Yasushi; WATANABE , Yukiyoshi; SHIMOJO , Eiichi; ICHIHARA , Teruyuki; ATAKA , Masashi; SHIBUYA , Katsuhiko; GOeRGENS, Ulrich; WO2011/18170; (2011); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 184177-83-1,Some common heterocyclic compound, 184177-83-1, name is 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, molecular formula is C30H35N5O3, 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.

EXAMPLE 2PREPARATION OF BENZYL POSACONAZOLE OF FORMULA (Ila); In a clean, dry round bottomed flask 23 ml of dimethylsulfoxide and 4.74 gm of compound of formula (III) were charged at room temperature and stirred for about 15 minutes. Previously prepared NaOH solution (0.53 gm of NaOH dissolved in 3.74 ml of water) was added into the flask at about room temperature and stirred for about 30 minutes. 5 gm of compound of formula (IVa) was added to the reaction solution and stirred at about 35C to about 40C for about 12 hours. After completion of the reaction, the reaction solution was cooled to about 0C and 50 ml of water was added dropwise and stirred for about 30 minutes. The formed precipitate was filtered and washed with 80 ml of water. The solid was dried in air oven at about 45C to about 50C to yield 6.6 gm of the title compound. Purity by HPLC: 92%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-((2S,3S)-2-(Benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one, its application will become more common.

Reference:
Patent; GLENMARK GENERICS LIMITED; GHARPURE, Milind; KRISHNA, Vivek; SANIKOMMU, Srinivas Reddy; CHAUDHARI, Ganesh; VERDIA, Jitendra; KHAN, Mubeen Ahmed; WO2011/158248; (2011); A2;,
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. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7N3O2

General procedure: General procedure: A mixture of 4-phenylurazole (1, 1 mmol), aryl aldehyde (2, 1.1 mmol) or ketone (5, 1.1 mmol), 1,3-diketone (3, 1 mmol) and FeCl3 (16.2 mg, 10 mol%) in acetonitrile (2.5 mL) was stirred in preheated oil bath at reflux for a specified time as required to complete the reaction (see Table 2 and 3). After complete conversion, as indicated by TLC, the solvent was removed in vacuo and the residue was diluted with water and extracted with ethyl acetate (2¡Á10 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (Merck, 60-120 mesh, ethyl acetate:hexane, 4:6) to afford the pure triazolo[1,2-a]indazoletrione or spirotriazolo[1,2-a]indazoletetraonederivative.

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 15988-11-1.

Reference:
Article; Subba Reddy; Umadevi; Narasimhulu; Yadav; Chemistry Letters; vol. 42; 8; (2013); p. 927 – 929;,
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, Recommanded Product: 288-88-0

j0185j Triethylamine (5.49 g, 54.30 mmol) is added to a solution of 1,2,4-triazole (3.0 g, 43.44 mmol) in DMF (50 mL) at rt. After stirring for 5 minutes, trityl chloride (12.11 g, 43.44 mmol) is added as a solid and the mixture is stirred overnight. The solvent is distilled off under reduced pressure and the crude is partitioned between dichloromethane (50 mL) and water (50 mL). The organic layer is separated and the aqueous layer is extracted with dichloromethane (3 x 50 mL). The combined organic layers are washed with water (3 x 40 mL). The organic layer is dried over Na2SO4 and concentrated under reduced pressure to afford the product 1-trytil-1H- 1,2,4-triazole (12.6 g, 93 %). n-BuLi (4.5 mL, 11.24 mmol; 2.5 M solution in hexanes) is added to a solution of 1-trityl-1H-1,2,4-triazole (3.5 g, 11.24 mmol) in THF (120 mL) at -78C and the solution is stirred for 45 mm. Bromine (1.76 g, 11.02 mmol) is added dropwise over a period of 5 minutes and the solution is stirred for 2 h allowed to warm to -20 C and quenched by adding saturated NH4C1 solution (30 mL). The reaction mixture ias diluted with water (60 mL) and dichloromethane (40 mL). The organic layer is separated and the aqueous layer is extracted with CH2C12 (4 x 50 mL).The combined organic extract was dried over Na2SO4 and the solvent evaporated under reduced pressure to afford crude which is used as such for the next step (4.2 g, 95 %). 7.09-7.16 (m, 6H), 7.27-7.40 (m, 9H), 7.86 (s, 1H).

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; NEWLINK GENETICS CORPORATION; KUMAR, Sanjeev; WALDO, Jesse; JAIPURI, Firoz; MAUTINO, Mario; WO2014/159248; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-70-2, The chemical industry reduces the impact on the environment during synthesis 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

[0864] lH-1,2,3-triazole-4-carboxylic acid (9.8 mg, 87f.tmol) and HATU (36.4 mg, 96 f.tmol) were combined in DMF(3.0 mL) and stirred at room temperature for 15 minutes. Compound 2 (40.3 mg, 87 fllllOl) and DIPEA (46 f.LL, 261f.tmol) were added and the resulting solution was stirred atroom temperature for 15 minutes, after which time LCMSindicated desired product formation. The solvent wasremoved in vacuo and the crude residue was purified byreverse phase chromatography to yield Compound c (34.5mg) as a TFA salt. MS m/z [M+Ht calc’d forC28H33ClFN50 4 , 558.22. found 558.

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-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

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

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. 4314-22-1, name is 2-(1H-1,2,3-Triazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4314-22-1

(ii) In a manner analogous to that described in Example 8 from (E)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-2′-(2-ethylbutyl)-4-methylvalerohydrazide and using 1,2,3-triazole-1-acetic acid in place of N-tert-butoxycarbonyl-beta-alanine there was obtained (E)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-2′-(2-ethylbutyl)-4-methyl-2′-[2-(1H-1,2,3-triazol-1-yl)acetyl]valerohydrazide in the form of a gum.

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 4314-22-1.

Reference:
Patent; Hoffmann-La Roche Inc.; US6239151; (2001); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics