Category: Triazoles

Synthetic Route of 103755-58-4, 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. 103755-58-4 name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, 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.

(1-Phenyl-1H-1,2,3-triazol-4-yl)methanol (0.37 g, 2.0 mmol) was added at 0 C to a mixture of potassium hydroxide (0.64 g, 5.0 mmol) and p-toluenesulfonyl chloride (0.45 g, 2.2 mmol) in tetrahydrofuran (8 mL). The mixture was stirred at room temperature for 3 h. The mixture was then diluted with ethyl acetate (20 mL) and washed with water (2 x 20 mL). The organic layer was dried over with MgSO4, concentrated in vacuo and the obtained crude product was purified by column chromatography (ethyl acetate/hexanes, 3:7) on a silica gel to give compound 2 (0.33 g, 50%) as a white solid; m.p. 104-106 oC. 1H NMR (300 MHz, CDCl3): delta = 8.00 (s, 1 H), 7.82 (d, J = 8.3 Hz, 2 H), 7.69-7.65 (m, 2 H), 7.56-7.43 (m, 3 H), 7.34 (d, J = 8.0 Hz, 2 H), 5.30 (d, J = 0.3 Hz, 2 H), 2.43 (s, 3 H). 13C NMR (75 MHz, CDCl3): delta = 145.3, 141.8, 136.8, 133.1, 130.1, 130.0, 129.3, 128.1, 122.3, 120.7, 63.2, 21.7. HRMS (ESI): calcd. for C16H16N3O3S [M + H]+ 330.0912; found 330.0913.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Kwon, Young-Do; Son, Jeongmin; Yun, Mijin; Chun, Joong-Hyun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2848 – 2852;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature 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.

G. (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid 2-methanesulfonyl-ethyl ester (R4=H; R7=-(CH2)2-SO2CH3) (2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid (207 mg, 501 mumol, 1.0 eq.), HOBt (0.2 g, 1.5 mmol, 3.0 eq.), and EDCI (260 muL, 3.0 eq.) were dissolved in DCM (4 mL). After stirring for 2 minutes, 2-(methylsulfonyl)ethanol (0.5 g, 4.0 mmol, 8.0 eq.) and 4-methylmorpholine (220 muL) were added. The mixture was stirred at room temperature for 2 hours. The reaction was quenched with water. The DCM layer was separated and concentrated, then purified by flash chromatography (10-100% EtOAc/hexanes). MeCN (2 mL) and 4 M of HCl in dioxane (0.5 mL) 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 (56.6 mg, 501 mumol, 1.0 eq.), HATU (190 mg, 501 mumol, 1.0 eq.) were dissolved in DMF (1 mL) and the resulting solution was stirred for 5 minutes, followed by the addition of DIPEA (262 muL) and the intermediate HCl salt. After 10 minutes, the reaction was quenched with AcOH and the product was purified by preparative HPLC to yield the title compound (28 mg; purity 95%). MS m/z [M+H]+ calc’d for C25H30N4O6S, 515.19. found 515.4.

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

Synthetic Route of 61-82-5,Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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.

Add 1.0 mmol of p-nitrobenzaldehyde, 1.0 mmol of ethyl acetoacetate, 1.0 mmol of 3-amino-1,2,4-triazole, and 0.18 g of magnetic nanosulfonic acid to 9 ml of ethanol-dimethylformamide, respectively. In an aqueous solution (V (ethanol): V (dimethylformamide): V (water) = 7: 2: 1) in a 50 ml three-necked flask with a stirrer and a condenser tube, stir well at room temperature. Heating to 86 C for 146min, TLC (thin plate chromatography) detection, raw material spots disappeared, magnetic nanosulfonic acid catalyst was adsorbed with a magnet while hot, the remaining reaction solution was cooled to room temperature, a large amount of solids were precipitated, the solids were crushed, and left to stand , Suction filtration, the obtained filter residue was washed with ethanol and vacuum-dried to obtain 7- (4-nitrophenyl) -5-methyl-4,7-dihydro- [1,2,4] triazolo [1, 5-a] Pyrimidine-6-carboxylic acid ethyl ester, the purity by liquid chromatography was 99.1%, and the calculated purity was 83%. The adsorbed magnetic nanosulfonic acid was put into the filtrate after suction filtration without any treatment, and p-nitrobenzaldehyde, ethyl acetoacetate, and 3-amino-1,2,4-triazole were directly added for repeated use.

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

Reference:
Patent; Ma’anshan Tai Bo Chemical Technology Co., Ltd.; Lu Hua; Shen Jianzhong; (11 pag.)CN110540540; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 16681-70-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16681-70-2 as follows.

[0430] IH-1,2,3-triazole-4-carboxylic acid (15.9 mg, 141f.tmol) and HATU (53.5 mg, 141 f.tmol) were dissolved in DMF (2 mL) and stirred for 15 minutes at room temperature.(2R,4R)-4-Amino-2-azido-5-(5′-chloro-2′-fluorobiphenyl-4-yl)pentanoic acid ethyl ester (50 mg, 128 f.tmol) and DIPEA(67 f.LL, 384 f.tmol) were added, and the mixture was stirred atroom temperature for 15 minutes then concentrated in vacuoand the residue was dissolved in EtOH (2 mL). An aqueoussolutionoflNNaOH (1.3 mL, 1.3 mmol)was added, and themixture was stirred at room temperature for 30 minutes thenconcentrated in vacuo and the residue was purified by reversephase chromatography to yield Compound 1 ( 45 mg).

According to the analysis of related databases, 16681-70-2, the application of this compound in the production field has become more and more popular.

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

15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, belongs to triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: Dimedone (0.14 g, 1 mmol), benzaldehyde (0.1 g, 1 mmol), and 4-phenylurazole (0.177 g, 1 mmol) were mixed with PEG-SO3H (0.6 g, 0.1 mmol) and the obtained mixture was stirred magnetically at 80 C for 40 min. After the completion of the reaction warm water (20 mL) was added and the mixture stirred for about 5 min. The insoluble crude product was filtered and recrystallized from EtOH/H2O 4:1 and the pure product was obtained (0.352 g, 91%). In order to recover the catalyst, the filtrate was dried under reduced pressure and recovered catalyst was washed with diethyl ether and reused after drying under reduced pressure. The equivalent procedure was used for the synthesis of triazolo[1,2-a]indazole-tetraones.

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

Reference:
Article; Hasaninejad, Alireza; Zare, Abdolkarim; Shekouhy, Mohsen; Tetrahedron; vol. 67; 2; (2011); p. 390 – 400;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27808-16-8, name is 4-Methyl-1H-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 27808-16-8, Recommanded Product: 4-Methyl-1H-1,2,3-triazole

A solution of 4-methyl-iH-i,2,3-triazole (500 mg,6.02 mmol), 2,3-dichloro-5-nitropyridine (1277.42 mg, 6.62 mmol), K2C03 (2491.22 mg, 18.05 mmol) in CH3CN (5 mE) was stirred at it for 12 h. The mixture was concentrated under reduced pressure, the crude product was purified by colunm chromatography over silica gel (petroleum ether ethyl acetate from 20:1 to 1:1). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford i25a (1.1 g, 76.3%) as a yellow solid. ECMS (ESI) mlz M+i: 239.7.

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

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 4928-88-5, 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. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 2 Preparation of methyl 1-(2,3,5-tri-O-Acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate Using a Mixture of beta/alpha-1,2,3,5-Tetra-O-acetyl-L-ribofuranose A 2 L flask was charged with 80.5 g of triazolemethylester, the above dichloromethane solution of beta/alpha-1,2,3,5-Tetra-O-acetyl-L-ribofuranose, and 37 g of acetic anhydride at ambient temperature.The mixture was distilled at atmospheric pressure (bath temperature, 90¡ã C.).When the pot temperature reached 85¡ã C. and the distillation became very slow, vacuum was applied (up to 30 mbar) and the distillation was continued for 40 minutes at 90¡ã C. (bath temperature) and then for another 40 minutes at 120¡ã C. (bath temperature, the pot temperature reached 117¡ã C.).The vacuum was released and 843 mg of triflic acid was slowly added.After the addition the vacuum was restored and the mixture was stirred at 115+-5¡ã C. (pot temperature) for 4 h.Upon the completion of the reaction the mixture was cooled to 70¡ã C. and to it was added 750 ML of 2B alcohol (ethyl alcohol).When a homogeneous solution was formed the mixture was cooled to 50¡ã C. and held until heavy precipitation formed (seeding might be necessary).The mixture was then slowly cooled to -5¡ã C. (bath temperature) in 2 h and held for at least 2 h.The solid was filtered, washed with 100 ML of cold 2B Alcohol (ethyl alcohol), and dried under vacuum at 50¡ã C. for 17 h to give 192.7 g (75.1percent yield from L-ribose) of methyl 1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate as an off-white solid.

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

Reference:
Patent; Dong, Zhiming; Zhang, Pingsheng; US2004/34213; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 41253-21-8,Some common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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.

Ethyl chloroformate (13g) was slowly added dropwise to the solvent of triazole sodium salt (9.1g) in tetrahydrofuran (30mL) at 20-30 C, and the reaction was completed at 20-30 C for 1h. After the reaction is completed, filter to obtain a solution of ethyl 1,2,4-triazole-1-carboxylate in tetrahydrofuran; from -40 to -30, slowly add a solution of ethyl 1,2,4-triazole-1-carboxylate in tetrahydrofuran. A solution of LDA (lithium diisopropylamide) in tetrahydrofuran (2M, 60mL) was added dropwise. After reaction for 30min, ethyl chloroformate (13g) was added dropwise. After stirring for 30min, the temperature was slowly raised to 20-30 C and stirred for 2h; After completion, add 30% aqueous sodium hydroxide solution to the system and react at 80 90 for 2h. After completion of the reaction, cool to 0 10 , add hydrochloric acid to adjust pH 2 3, and filter to obtain 1, 2, 4-triazole -3-carboxylic acid, yield 82%.

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

Reference:
Patent; Shanghai Dongyue Pharmaceutical Co., Ltd.; An Na; Liu Xinke; Long Zhongzhu; Cai Chang; Cai Shuihong; (5 pag.)CN110903255; (2020); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7411-23-6,Some common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-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.

To a suspension of NaH (60% in mineral oil, 387.9 mg, 9.7 mmol) in THF (20 mL) at 0C is added a solution of A6a (2.0 g, 8.8 mmol, Matrix) in THF (20 mL). The reaction mixture is allowed to warm to RT and is stirred for 30 mm. It is then cooled again to 0C and A6b (1 .9 mL,10.6 mmol, Combi Blocks) is added. The reaction mixture is stirred overnight at RT and diluted with EtOAc (50 mL). The organic layer is washed with water (30 mL) and brine (30 mL), dried over MgSO4, and filtered. The filtrate is concentrated to give A6c which is used without further purification.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; BILODEAU, Francois; POIRIER, Maude; PARISIEN, Mathieu; KUHN, Cyrille; THIBEAULT, Carl; TRINH, Thao; WO2014/70978; (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. 6086-21-1, name is 1-Methyl-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C3H5N3

[00161] To a stirred solution of SM-1 (2.0 g, 24.0 mmol) in THF (20 mL) was added n- butyl lithium (19 mL, 12.0 mmol) at -78 ¡ãC dropwise and stirred for 2 h. Then solid CO2 (2 g) was added and stirred at -78 ¡ãC for 1 h. The reaction mass was stirred at RT for 16 h. After consumption of the starting material (by TLC), the reaction mixture was quenched with water (3 mL) and the obtained solid was filtered. The solid was triturated with diethylether/n-pentane (10 mL/10 mL). The white color solid was dried under vaccum to afford Int-J (2.0 g, 65.7percent) as white solid. 1H-NMR: (500 MHz, DMSO-i): delta 7.70 (s, 1H), 4.01 (s, 3H) LCMS m/z: 128.3 [M++l]

The synthetic route of 6086-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAUREX, INC.; LOWE, John, A.; KHAN, M., Amin; WO2014/120800; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics