Triazoles

Electric Literature of 626248-56-4, A common heterocyclic compound, 626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline, molecular formula is C8H8N4, 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.

To 130 mg (0.37 mmol) of 2, 118 mg of the 3-(2H-l,2,3-triazol-2-yl)aniline (1.2 eq), 107 mg NaCvBu (3 eq), 85 mg Pd(dba)2 (0.4 eq), and 53 mg Q-Phos (Aldrich 675784, 0.2 eq) was added ~5 mL dry toluene. The reaction mixture was degassed with Ar for 10 min and then refluxed under argon at 110C for 3 hours. The reaction mixture was cooled and diluted with EtOAc, washed with water and brine, dried over MgSC^, and concentrated. The resulting oil was dissolved in a 3: 1 mixture of TFA/H2S04. The mixture was heated to 80C for 1 hour and then cooled to room temperature. Approximately 10 mL H20 was added to the mixture and the resulting solution was subjected to reverse phase preparative HPLC. Product was isolated by utilizing a mobile phase with 0.1% TFA in water as solvent A and 0.1% TFA in acetonitrile as solvent B and eluting with a 15% to 50% B mixture over 10 minutes.[0527] Yield: 23 mg. UV: 265, 306 nm. M+H found for C^H^NsO: 393.3. NMR(CD3OD): 8.96 (IH, br), 7.96 (2H, s), 7.82 (IH, d, J=8.8Hz), 7.67 (IH, d, J=6.0Hz), 7.42 (IH, t, J=6.0Hz), 7.17 (IH, d, J=5.6Hz), 6.18 (IH, d, J=8.8Hz), 4.78 (IH, br), 3.65 (IH, br), 1.90-1.45 (8H, m) ppm.

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; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

[0664] To a solution of 3H-[1,2,3]triazole-4-carboxylicacid (77 mg, 688 flillOl) and HATU (130 mg, 344 f.tmol) inDMF (1.5 mL) was added DIPEA (160 f.LL, 920 flillOl). Themixture was stirred at room temperature for 20 minutes, followedby the addition of Compound 11 (140 mg, 210 f.tmol).The mixture was stirred at room temperature for 20 minutes,then the reaction was quenched with 10% aqueous citric acid(15 mL) to pH 4. The mixture was extracted with EtOAc(3×20 mL ), washed with saturated aqueous NaCl (1 0 mL) anddried over MgS04 . The mixture was filtered and the filtratewas evaporated. The residue was purified by flash chromatography(10-100% hexanes/EtOAc gradient over 45 minutes).The fractions containing the desired product were combinedand evaporated. The residue was dried in vacuo at roomtemperature overnight to yield Compound 12 (70 mg). LCMS(ESI): calc. C33H33ClFN50 5 =634.1; obs. rn/z 634.2[M+Ht. Retention time 5.96 min.

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

Synthetic Route of 288-36-8, 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. 288-36-8, name is 1H-1,2,3-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

Example 58:; N-[6-(3-MethyI-3H-[l,2,3]triazol-4-yl)-2,4-dioxo-7-trifluoromethyl-l,4-dihydro-2H- qninazoIin-3-yI]-methanesulfonamide; 1 -Methyl-1H-[1 ,2,3]triazole; To a solution of NaOMe (3.91 g, 72.4 mmol) in MeOH (50 mL) was added 1,2,3-lH-triazole (5 g, 72.4 mmol). The mixture was then cooled to 0 0C and MeI (4.53 mL, 72.4 mmol) was added dropwise. The mixture was stirred allowed to warm up to r.t. and stirred at this temperature for 2 h. The solvent was removed in vacuo, the residue was treated with hot toluene (40 mL) and then filtered to afford a yellow paste. This paste was slurried in hot CHCl3 and the solid was filtered off. The solid was washed with hot CHCl3 (2 X). The filtrates were combined, concentrated in vacuo and the residue distilled (112-116 0C, water pump) to afford a mixture of starting material and final product. The distillate was dissolved in THF and NaH was added portionwise. The insoluble material was filtered off, washed with Et2O and concentrated in vacuo to afford l-methyl-lH-[l,2,3]triazole (1.33 g, 22%) as a yellow syrup.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/108591; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 3641-08-5,Some common heterocyclic compound, 3641-08-5, name is 2H-1,2,4-Triazole-3-carboxamide, molecular formula is C3H4N4O, 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 3 Preparation of 1(or 2 or 4)-(p-Bromophenylsulfonyl)-s-triazole-3-carboxamide To a cooled, stirred mixture of 3.0 g. of 1,2,4-triazole-3-carboxamide and 6.9 g. of bromobenzenesulfonyl chloride in 125 ml. of anhydrous ether is added rapidly 2.75 g. of triethylamine. The cooling bath is removed and the mixture is stirred at room temperature for 23 hours. The heterogeneous mixture is filtered and washed successively with ether, cold water and then ether and dried in vacuo at room temperature for 7 hours, to obtain a crude colorless solid. This material is heated in about 50 ml. of dry acetonitrile and the hot mixture is filtered. The pale yellow filtrate is concentrated to about 10 ml. by water pump evacuation. The colorless solid which separates is collected and washed with acetonitrile then dried in vacuo overnight. To remove final, very minute impurities, the product obtained is then thoroughly washed with water, filtered and dried in vacuo overnight, m.p. 130-136 C.

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

Reference:
Patent; American Cyanamid Company; US4007198; (1977); A;,
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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C2HBr2N3

In a 100 mL round-bottomed flask, 3,5-dibromo-lH-l ,2,4-triazole (5g, 22.0 mmol, Eq: 1.00), l-(chloromethyl)-4-methoxybenzene (3.45 g, 22.0 mmol, Eq: 1) and N-ethyl-N- isopropylpropan-2-amine (5.7 g, 44.1 mmol, Eq: 2) were combined with acetonitrile (101 ml) to give a light yellow solution. Potassium iodide (1.83 g, 11.0 mmol, Eq: 0.5) was added. The mixture was heated to reflux for 2 hours. The reaction mixture was cooled and diluted with EtOAc (100 mL), washed with H20 (50 mL) and brine (50 mL). The organic layer was dried over anhydrous MgS04, filtered and volatiles were removed under reduced pressure to yield an oil from which the compound was isolated by column chromatography (Hexanes/EtOAc = 70/30) to product 7.3 g (95%).

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 7411-23-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (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. 288-36-8, name is 1H-1,2,3-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Product Details of 288-36-8

A solution of 1,2,3-triazole (430 mg, 6.23 mmol), 2-chloro-3-nitrothiophene (1.02 g, 6.23 mmol) and potassium t-butoxide (838 mg, 7.48mmol) in DMF (20 mL) was stirred at 90 0C for 4 h, after which the reaction mixture was cooled to room temperature and diluted with Et2O. The solution was washed with brine and the organic phase was separated, dried (Na2SO4), filtered, concentrated under vacuum and purified by silica gel column chromatography (eluant hexane/ethyl acetate, 8/2 to 1/1) to give a 1 :1 mixture of 2-(3-nitrothiophen-2-yl)-2H- 1,2,3-triazole and l-(3-nitrothiophen-2-yl)-lH-l,2,3-triazole (1.08 g, 5.55 mol, 89%). Retention time (min) = 1.256 and 1.701, method [1], MS(ESI) 197.0 (M+Eta).The nitrothiophene and 10% palladium on carbon in ethyl acetate (e.g., 3 mL) was shaken under a hydrogen atmosphere (e.g., 40 psi) for about 2 h. The resulting suspension was filtered through a pad of diatomaceous earth and the filtrate was concentrated under vacuum.The title compound was prepared from 2-(3-nitrothiophen-2-yl)-2H- 1,2,3- triazole and l-(3-nitrothiophen-2-yl)-lH-l,2,3-triazole (514 mg, 2.61 mmol) according to protocol F to give a 1/1 mixture of 2-(2H-l,2,3-triazol-2-yl)thiophen-3-amine and 1-(1H-1,2,3- triazol-2-yl)thiophen-3 -amine (431 mg, 2.61 mmol, quantitative). Retention time (min) = 0.581 and 1.035, method [1], MS(ESI) 167.0 (M+Eta).

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); 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. Product Details of 16681-70-2

I. (2S,4S)-5-Biphenyl-4-yl-2-hydroxymethyl-4-[(3H-[1,2,3]-triazole-4-carbonyl)-amino]-pentanoic acid 2-morpholin-4-yl-ethyl ester (R7=-O-(CH2)2-morpholine)(2S,4S)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-pentanoic acid (100 mg, 250 mumol, 1.0 eq.), HOBt (0.2 g, 1.5 mmol, 6.0 eq.), and EDCI (260 muL, 6.0 eq.) were dissolved in DCM (2 mL). After stirring for 10 minutes, 4-morpholineethanol (330 mg, 2.5 mmol) was added. The mixture was stirred at room temperature until the reaction was complete (3 hours). The mixture was then diluted with DCM and washed with saturated aqueous NaHCO3. The organic layer was separated, dried, and concentrated. MeCN (2.5 mL) and 4 M of HCl in dioxane (250 muL) were added and the resulting mixture was stirred at room temperature for 1 hour. The solvent was removed to provide the intermediate HCl salt, which was used in the following coupling step. 1,2,3-Triazole-4-carboxylic acid (28.3 mg, 250 mumol, 1.0 eq.) and HATU (95 mg, 250 mumol, 1.0 eq.) were dissolved in DMF (2.0 mL) and the resulting solution was stirred for 5 minutes, followed by the addition of DIPEA (87.2 muL) and the intermediate HCl salt. After 5 minutes, the mixture was diluted with EtOAc then washed with saturated aqueous NaHCO3. The organic layer was separated, concentrated and purified by preparative HPLC to yield the title compound (60 mg; purity 95%). MS m/z [M+H]+ calc’d for C27H33N5O5, 508.25. found 508.4.

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, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-65-5, 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. 16681-65-5 name is 1-Methyl-1H-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.

A solution of n-butyllithium in hexanes (2.5 M, 22.5 mL, 56.3 mmol) was added dropwise by syringe to a stirring solution of 1-methyl-1H-1,2,3-triazole (5.00 g, 60.2 mmol, prepared according to PCT Int. Appl., 2008098104) in dry tetrahydrofuran (400 mL) at -55 C. The resulting off-white slurry was stirred at -45 C. for 20 minutes, whereupon a solution of 2,6-dimethyl-pyridine-3-carbaldehyde (8.33 g, 61.7 mmol) in dry tetrahydrofuran (10 mL) was added dropwise by syringe. After 5 minutes, the cooling bath was removed and the reaction mixture was allowed to slowly warm. After 45 minutes, saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (100 mL) were added. The mixture was concentrated by rotary evaporation. The residue was dissolved in ethyl acetate (300 mL). The organic solution was washed with saturated aqueous sodium chloride solution (100 mL, containing excess solid sodium chloride). The aqueous layer was extracted with ethyl acetate (2*100 mL). The organic layers were combined and the combined solution was concentrated. Ether (100 mL) was added to the residue and the mixture was sonicated for 20 minutes during which time a white solid crashed out. The solids were collected by filtration. Ether (100 mL) was added to the collected solids and the mixture sonicated a second time. After 20 minutes, the mixture was filtered and the solids were collected to provide the title compound as a fine powder.

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

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); 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. 6818-99-1, name is 3-Chloro-1,2,4-triazole, A new synthetic method of this compound is introduced below., Quality Control of 3-Chloro-1,2,4-triazole

A mixture of 3-chloro-lH-l,2,4-triazole (2.76 g, 26.7 mmol), 1- chloro-2-methoxy-4 -nitrobenzene (5.0 g, 26.7 mmol), potassium hydroxide flakes (1.496 g, 26.7 mmol), and DMSO (25 mL) was heated in a sealed reaction vessel 100 0C for 24 h. The reaction was allowed to cool to rt and additional portions of 3- chloro-lH-l,2,4-triazole (1.38 g, 0.5 equiv) and potassium hydroxide (0.75 g, 0.5 equiv) were added. The reaction vessel was resealed and heated to 1100C for an additional 24 h. The resulting mixture was allowed to cool to rt and was poured into 500 mL of water. The aqueous mixture was extracted with EtOAc (3 x 100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified using silica gel chromatography (0-5% MeOH/chloroform, linear gradient over 144 min, flow 25 mL/min) to afford 2-(3-chloro-lH-l,2>;4-triazol-l-yl)-5-nittophenol (0.924 g, 3.84 mmol, 14.4 % yield). LC-MS (M+H)+ – 241.0. 1H NMR (500 MHz, chloroform-^ delta ppm 11.97 (br. s., 1 H) 9.24 (s, 1 H) 7.90 – 7.95 (m, 1 H) 7.89 (d, J=2.44 Hz, 1 H) 7.84 (dd, J=8.85, 2.44 Hz, 1 H).

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; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); 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. 10570-40-8, name is 4-Methyl-4H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C3H5N3

Step 1. This step is the same as the preparation of Step 1 in Example 1.Step 2. 40 mmol of 4-methyl-1,2,4-triazole and 100 mmol of vinyl chloride were stirred under nitrogen at 70 C, and condensed and refluxed for 36 h to complete the quaternization reaction, and the reaction product was washed with carbon tetrachloride. Rotary steaming to obtain a light yellow liquid1,2-Divinyl-4-methyl-1,2,4-triazole chloride 7.65 g.

According to the analysis of related databases, 10570-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Tech University; Guan Guofeng; Ding Jing; He Yuting; Li Xue; Yuan Dashui; Wan Hui; Wang Lei; (9 pag.)CN108250227; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics