Category: Triazoles

Synthetic Route of 7170-01-6, A common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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 a solution of 3-methyl-1H-1,2,4-triazole (7.3 g, 88 mmol) in DMF (75 mL) was added K2CO3 (60.7 g, 439 mmol) and 2-bromopropionic acid tert-butyl ester (14.6 mL, 88 mmol). The reaction was stirred at room temperature overnight. The mixture was diluted with EtOAc (500 mL), washed with water (¡Á3) then brine. Dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/isohexane (20 to 100%) to give 13 g of crude product as a 3:1 mixture of regioisomers. The mixture was purified by Chiralcel OD with a gradient from 4% to 30% IPA/Heptane. Then the first two peaks were separated with Chiracel OD column isocratically eluting with 4% IPA/Heptane. The second peak was collected as the desired single stereoisomer (R or S) (2-(3-methyl-1H-1,2,4-triaol-1-yl)propanoic acid tert-butyl ester) (3.5 g, 19%). 1H-NMR (500 MHz, CDCl3) delta 8.05 (s, 1 H), 4.90 (q, J=7 Hz, 1 H), 2.35 (s, 3 H), 1.72 (d, J=7 Hz, 3 H), 1.40 (s, 9 H). ESI-MS calculated for C10H17N3O2: Exact Mass: 211.13; Found 156.05 (-tBu).

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berger, Richard; Chang, Lehua; Edmondson, Scott D.; Goble, Stephen D.; Ha, Sookhee Nicole; Kar, Nam Fung; Kopka, Ihor E.; Li, Bing; Morriello, Gregori J.; Moyes, Chris R.; Shen, Dong-Ming; Wang, Liping; Zhu, Cheng; US2009/253705; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. name: 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

Add to a 50ml single-mouth bottle1-((2S,3S)-2-(Benzyloxy)-pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)- 1H-1,2,4-Triazole-5(4H)-one (1 g), 12 mol/L hydrochloric acid (5 ml) was stirred at 50 C.After 8 h, the dissolution was complete and TLC showed the reaction was complete.After cooling to room temperature, 6 mol/L NaOH (9 ml) was added, and NaHCO3 (10 ml) was evaporated, and water (10 ml) was added and stirred for 1 hour to form a solid. Filter by suction, wash the filter cake water (10ml),Recrystallization from isopropanol / toluene gave 0.7 g of a white solid, yield 85%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 184177-83-1, its application will become more common.

Reference:
Patent; Yangzijiang Pharmaceutical Group Co., Ltd.; Shanghai Pharmaceutical Industry Institute; Huang Huoming; Lv Huimin; Xiao Zhichao; Cai Wei; Ren Zhongjie; Zhou Ting; Liu Zhenren; Zhou Weicheng; Zhang Haibo; (35 pag.)CN108341754; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

3H-l,2,3-triazole-4-carboxylic acid (3.4 mg, 30 muiotaetaomicron) was combined with HATU (1 1 mg, 30 muiotaetaomicron) in DMF (0.3 mL) and stirred at room temperature for 10 minutes; (1418) DIPEA (1 eq.) was added and the mixture was stirred for 1 minute. Compound 2 (10 mg, 30 muiotaetaomicron) in DMF (0.5 mL) was combined with DIPEA (5.2 muEpsilon, 30 muiotaetaomicron), then added to the activated acid solution. The resulting solution was stirred at room temperature for 30 minutes; LC/MS showed the mass of the desired product. The solvent was removed in vacuo and the crude residue was purified by reverse phase chromatography to yield Compound a (8.5 mg) as a TFA salt. MS m/z [M+H]+ calc’d for C27H31CIFN5O4, 544.21 ; found 545.2.

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

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 15988-11-1, These common heterocyclic compound, 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, 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.

General procedure: General procedure for the synthesis oftriazolo[1,2-a]indazole-trione (1a-g) and2H-indazolo[2,1-b]phthalazine-triones (2a-g)To a well-ground mixture of arylaldehyde (1 mmol), dimedone(0.140 g, 1 mmol) and 4-phenylurazole (0.177 g, 1 mmol) or2,3-dihydrophthalazine-1,4-dione (0.162 g, 1 mmol), was added[Et3N-SO3H]HSO4[(0.028 g, 0.1 mmol) for the preparation of1a-gor (0.042 g, 0.15 mmol] for the synthesis of2a-g}. Theobtained mixture was firstly stirred magnetically at 90C, andafter solidification of the reaction mixture, it was stirred with asmall rod at same temperature. After the reaction was completed(as observed by TLC), the reaction mixture was cooled to roomtemperature, water (2 mL) was added, stirred for 3 min, andfiltered. The solid residue was recrystallized from EtOH/H2O(4/1) to give the pure product.

The synthetic route of 15988-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zare, Abdolkarim; Masihpour, Fatemeh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 8; (2016); p. 1160 – 1165;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 138479-53-5, These common heterocyclic compound, 138479-53-5, name is 2-[1,2,4]Triazol-1-yl-benzaldehyde, 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 a round bottom flask is added 4-(2-amino-4-methoxy-pyrimidin-5-yl)-N^-ieri-butyl- benzene- 1,2-diamine (118 mg, 0.411 mmol) in DMF (4 mL) and water (1 mL), followed by the addition of 2-1,2,4-triazol-l-yl-benzaldehyde (78 mg, 0.45 mmol) and oxone (51 mg, 0.443 mmol). The reaction mixture is stirred at room temperature for 4 hours. Sat. sodium thiosulfate (10 mL) is added. The reaction mixture is diluted with EtOAc. The organic layer is separated, washed with water then brine, dried with Na2S04, filtered and concentrated. The residue is loaded into a silica gel column. The column is eluted with 0- 4% 7M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford the title compound (67 mg, 37 %) as a light brown solid. LCMS (ESMS): m/z 441.73 (M++l)

The synthetic route of 138479-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; HAO, Ming-Hong; LIU, Weimin; LO, Ho-Yin; LOKE, Pui Leng; MAN, Chuk, Chui; MORWICK, Tina, Marie; NEMOTO, Peter, Allen; TAKAHASHI, Hidenori; TYE, Heather; WU, Lifen; WO2011/68821; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 27996-86-7, These common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, 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.

General procedure: NaOAc anhydrous (17.6mg, 0.21mmol), the appropriate aldehyde derivative (0.14mmol), and intermediate 6 (25.4mg, 0.07mmol) were dissolved in AcOH (3mL) and stirred at 110C for 16h. After cooling, the mixture was neutralized to pH 8 by addition of NH4OH and extracted with DCM. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, DCM/MeOH 15/1 v/v including 1% of NH4OH) to produce the final target compounds.

The synthetic route of 27996-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elkamhawy, Ahmed; youn Kim, Nam; Hassan, Ahmed H.E.; Park, Jung-eun; Yang, Jeong-Eun; Elsherbeny, Mohamed H.; Paik, Sora; Oh, Kwang-Seok; Lee, Byung Ho; Lee, Mi Young; Shin, Kye Jung; Pae, Ae Nim; Lee, Kyung-Tae; Roh, Eun Joo; Bioorganic Chemistry; vol. 92; (2019);,
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. 626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 626248-56-4

Example No. 262Preparation of N- (3 – (2H-1, 2 , 3 -triazol-2 -yl) phenyl) -5-(thiophen-2-yl) -IH-pyrazolo [4 , 3-d] pyrimidin-7-amine7-chloro-2- (4-methoxybenzyl) -5- (thiophen-2-yl) -2H- pyrazolo [4 , 3 -d] pyrimidine (0.16 mmol) and 3 – (2H- 1 , 2 , 3 -triazol- 2-yl)aniline (0.3 mmol 2 eq.,) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 360.1031 g/molHPLC-MS: analytical method Drt : 6.78 min – found mass: 361 (m/z+H)

The synthetic route of 626248-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); 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. 15294-81-2, name is 4,5-Dibromo-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 15294-81-2

EXAMPLE 4 1(2 or 3)-N,N-Diethylcarbamyl-4,5-dibromo-1H-1,2,3-triazole STR13 To a suspension of 213 milligrams (mg) (8.89 mmoles) of sodium hydride in 20 ml of anhydrous tetrahydrofuran was added 2 g (8.89 mmoles) of 4,5-dibromo-1H-1,2,3-triazole. The resulting suspension was cooled to 0¡ã C. and 1.2 g (8.89 moles) of N,N-diethylcarbamoyl chloride was added by drop. The reaction mixture was heated to reflux overnight and the precipitated sodium chloride was removed by filtration. Concentration of the filtrate in vacuo gave 2.4 g (82percent) of 1(2 or 3)-N,N-diethylcarbamyl-4,5-dibromo-1H-1,2,3-triazole as a yellow oil. The structure was confirmed by n.m.r. and I.R.

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; Stauffer Chemical Company; US4596596; (1986); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1186050-58-7, A common heterocyclic compound, 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C9H6FN3O2, 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.

A mixture of [6-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-2-trifluoromethyl-pyrimidin- 4-yl]-dimethyl-amine (50 mg, 0.17 mmol), 2-fluoro-6-[1 ,2,3]triazol-2-yl-benzoic acid (37.8 mg, 0.18 mmol), HATU (94.6 mg, 0.25 mmol) and DIPEA (0.09 mL, 0.50 mmol) in DMF (4.0 mL) was stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate (60.0 mL) and washed with water (2 X 100 mL). The organic phase was dried (Na2SO ), filtered and concentrated to dryness. The crude product was purified using Agilent HPLC (Basic system) to yield pure title compound (19.0 mg, 23.4 %). MS (ESI) mass calcd. for C22H22F4N8O, 490.46; m/z found [M+H]+. 1 H NMR (CDCI3): 7.89-7.79 (m, 2H), 7.74 (s, 1 H), 7.55-7.37 (m, 1 H), 7.21 -7.05 (m, 1 H), 5.25-5.09 (m, 1 H), 4.25-3.51 (m, 6H), 3.50-2.95 (m, 10H).

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; JANSSEN PHARMACEUTICA NV; CHAI, Wenying; LETAVIC, Michael, A.; LY, Kiev, S.; PIPPEL, Daniel, J.; RUDOLPH, Dale, A.; SAPPEY, Kathleen, C.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; SOYODE-JOHNSON, Akinola; STOCKING, Emily, M.; SWANSON, Devin, M.; WO2011/50198; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1001401-62-2, 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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

A solution of the product from step 3 (72 mg, 0.19 mmoi), 2-(2H-i,2,34riazoi-2- yi)henzoic acid (41.6 mg, 0.22 mmol) and HATU (150 mg, 0.39 mmol) in DMF/DIEA (4 mL/0.5mL) was stirred at RT overnight. After LCMS indicated the reaction completed, the mixture was purified by Prep-HPLC to give the title compound (50 mg) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 2-(2H-1,2,3-Triazol-2-yl)benzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics