Category: Triazoles

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. 584-13-4, name is 4H-1,2,4-Triazol-4-amine, This compound has unique chemical properties. The synthetic route is as follows., 584-13-4

Example-2 4-Amino-1-[3,5-bis-(1-cyano-1-methylethyl)benzyl]-1H-[1,2,4]triazolium bromide (8) (Q. A.-Salt) Isopropanol (1.5 L), 3,5-bis-(1-cyano-1-methylethyl)benzylbromide (2) (100 g) and 4-amino-1,2,4-triazole (22.5 g) were charged in a flask at room temperature. The reaction mass was heated at 80-85 C. for next 5 hours. The reaction mass was further cooled down to room temperature and stirred for next one hour at 25-35 C. The precipitated solid QA-salt was filtered and washed with fresh isopropanol (100 mL*2). The Q.A.-salt was dried at 60-70 C. till LOD is less than 1.0%, giving solid product (74.4 g). m.p.: 198-200 C.

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; Solanki, Kirtipalsinh Saijansinh; Pal, Gautam; Haider, Hussain; Singh, Manoj Kumar; Kothari, Jay Shantilal; Agarwal, Virendra Kumar; US2009/221837; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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 7170-01-6. 7170-01-6

A mixture of compound precursor 5b (150 mg, 0.35 mmol), 3-methyl-1,2,4-triazole (581 mg, 7 mmol; 20 eq.; prepared by the method described in Coll. Czech. Chem. Comm. 1985, 49, 2492), copper powder (45 mg, 0.7 mmol; 2 eq.), potassium carbonate (97 mg, 0.7 mmol; 2 eq.) was flushed with anhydrous nitrogen and heated in a sealed tube at 160 C. for 11 h. Upon cooling, to the mixture was added MeOH, and the insoluble material was filtered. The filtrate was concentrated in vacuo and purified by C-18 reverse phase column (Prep. System eluting with MeOH-water containing 0.1% TFA) to obtain 19 mg (0.040 mmol, Y. 11%) of the title compound Example 216 as amorphous powder (TFA salt): MS m/e 474 (MH); 1H NMR (DMSO-d6) delta ppm 2.50 (3H, s, overlapped with DMSO peaks), 3.44 (4H, br, CH2N), 3.68 (4H, br, CH2N), 4.00 (3H, s, CH3O), 7.46 (5H, br. s, Ar-Hs), 7.89 (1H, s), 8.25 (1H, s), 9.24 (1H, s), 12.41 (1H, s, NH).

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 3-Methyl-1H-1,2,4-triazole.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, 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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol~2-yl)-5-methylbenzoic acid, followed by the undesired regioisomer isomer, I -(2H- 1 ,2,3-triazoI-2-yl)-5-methylbenzoic acid. A solution of the acid (3.56 g, 17.52 mmol) in 150 mL of DCM was stirred and cooled to O0C. The solution was treated with oxalyl chloride (1.9 mL, 21.9 mmol) and DMF (68 muL, .878 mmol). The solution was slowly warmed to room temperature and stirred overnight. Solvent was concentrated and the resulting solid was azetroped with DCM and concentrated to provide A-7 as a yellow solid.

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; MERCK SHARP & DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; SCHREIER, John, D.; WHITMAN, David, B.; WO2010/48010; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 584-13-4 name is 4H-1,2,4-Triazol-4-amine, 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. 584-13-4

General procedure: The ligand 4-(1H-imidazol-5-ylmethylene-amino)-4H-1,2,4-triazole (5-imztrz) (Fig. 1) was prepared by the condensation reaction of a modified literature procedure [21]. The dissolved 4-amino-1,2,4-triazole (1.68 g, 0.02 mol, 1.0 eq.) in ethanol was heated to boiling (80 C). Then, the second reactant 1H-imidazole-4-carbaldehyde (2.11 g, 0.022 mol, 1.1 eq.) dissolved in ethanol was added dropwise though a dropping funnel. After the complete addition few drops of catalytic H2SO4 were added. The reaction mixture was kept for refluxing for another 10 h. After cooling down to r.t., the excess of solvent was removed by rotary evaporator at 35 C. The obtained product was washed with small amounts of cold ethanol, diethyl ether and then dried in the desiccator with phosphorus pentoxide as dry agent. A light-yellow powder was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4H-1,2,4-Triazol-4-amine, and friends who are interested can also refer to it.

Reference:
Article; Li, Ai-Min; Rentschler, Eva; Polyhedron; vol. 154; (2018); p. 364 – 372;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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, 184177-83-1, 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.

Example-20: Preparation of 4-(4-(4-(4-(((3R,5R)-5-((1H-i,2,4-triazol-1-yi)methyl)-5-(2,4- difluorophenyl)tetrahydrofuran-3-yI)methoxy)phenyl)piperazin-1-yI)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yI)-1H-1,2,4-triazol-5(4H)-oneSodium hydroxide solution [prepared by dissolving sodium hydroxide (7.8 gins) in water (10 ml)] was added to dimethyl sulfoxide (175 ml) at 25-30C. ((3S,5R)-5-((1H-1,2,4-triazol-1- yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzene sulfonate (48.12 gms) and then followed by 1 -((2S,3 S)-2-(benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin- 1 -yl)phenyl)- 1 H-i ,2,4-triazol-5(4H)-one (50.Ogms) was added to the reaction mixtureat 25-30C. Heated the reaction mixture to 38-43C and stirred for 10 hours at the same temperature. Cooled the reaction mixture to 25-30C and slowly added to water at the same the same temperature. Cooled the reaction mixture to 10-15C and adjusted the pH of the reaction mixture to 7.0 using hydrochloric acid solution at the same temperature. Raised the temperature5 of the reaction mixture to 25-30C and stirred for 3 hours at the same temperature. Filtered the precipitated silid and washed with purified water. To the obtained wet compound, isopropanol (500 ml) was added at 25-30C. Heated the reaction mixture to 65-70C to get clear solution. Cooled the reaction mixture to 25-30C and stirred for 4 hours at the same temperature. Filtered the precipitated solid, washed with isopropanol and dried to get the title compound.10 Yield: 69.29 gins.

Statistics shows that 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 is playing an increasingly important role. we look forward to future research findings about 184177-83-1.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; SAHADEVA REDDY, Maramreddy; WO2015/59716; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common heterocyclic compound, 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, molecular formula is C3H4ClN3O, 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. 252742-72-6.

Example 54 (3R*,4R*)-N-[3,5-bis(trifluoromethyl)benzyl]-3-(4-fluoro-2-methylphenyl)-N-methyl-1-[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]piperidine-4-carboxamide hydrochloride To a solution of the compound (0.30 g) obtained in Example 12 and potassium carbonate (0.083 mg) in 1percent H2O-DMF (5.0 mL) was added 5-(chloromethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (0.094 g) at 0¡ãC, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the product was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC. 1H-NMR(CDCl3)delta: 1.70-2.00 (1H, m), 2.05-2.40 (6H, m), 2.75-3.10 (6H, m), 3.45-3.49 (2H, m), 3.65-3.80 (1H, m), 4.16 (1H, d, J=15.0Hz), 4.88 (1H, d, J=15.0Hz), 6.70-6.80 (2H, m), 7.00-7.18 (1H, m), 7.33-7.40 (2H, m), 7.70-7.82 (1H, m), 10.21 (1H, br s), 10.3-11.0 (1H, br) The obtained product was treated with 1 equivalent of 4N hydrogen chloride/ethyl acetate solution to give the title compound as a white powder (0.28 g, 78percent). MS(ESI+): 574(M-HCl+H)

The synthetic route of 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1705176; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 423165-07-5

General procedure: A mixture of trisallene 3 (0.25 mmol), aryl/heteroaryl iodides (0.90 mmol), nucleophiles (0.90 mmol), Pd2(dba)3 (7.5 mol %), TFP (tri-(2-furyl)phosphine) (30 mol %), and K2CO3 (2.25 mmol) in MeCN (5 mL) was stirred and heated at 80 C (oil bath temperature) until the starting material was completely consumed as monitored by TLC (see Table 1). The mixture was cooled and solvent removed under vacuo. The residue was dissolved in CHCl3 (25 mL) and extracted with H2O (20 mL) three times. The organic layer was dried over anhydrous MgSO4 and evaporated under rotatory evaporator to give the crude product, which was purified by flash chromatography.

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, 423165-07-5, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gueltekin, Zeynep; Elboray, Elghareeb E.; Aly, Moustafa F.; Abbas-Temirek, Hussien H.; Shepherd, Helena J.; Grigg, Ronald; Tetrahedron; vol. 70; 33; (2014); p. 4934 – 4941;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of compound 12 (0.8 g; 4.5 mmol) in N-methylpyrrolidone (5 ml), water (0.5 ml) and hydrochloric acid (5-6 drops) were added. The mixture was stirred at 100C for 6 h. The mixture was cooled to room temperature and water (100 ml) was added. Then NaHCO3 sat. (20 ml) was added, the product was extracted with EtOAc (5¡Á20 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 13 (0.6 g, 81%) as pink solid. A solution of compound 13 (1.8 g; 11 mmol) in POCl3 (20 ml) was stirred at 100 C for 12 h. Then POCl3 was evaporated under reduced pressure. To a residue ice water (100 ml) and then NaHCO3 sat. (25 ml) were added, the product was extracted with EtOAc (3¡Á35 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 14 (0.8 g, 40%) as light-yellow solid At 143C, to a melt 3-methyl-1H-1,2,4-triazole (744 mg, 8.95 mmol) under N2 atmosphere was added compound 14 (392 mg, 1.79 mmol). After stirring for 20 hrs, the reaction mixture was cooled down to r.t. and partitioned between H2O (20 mL) and EA (20 mL). The layers were separated and the aqueous layer was extracted with EA (20 mL x 3). The combined organic layers was dried over Na2SO4, filtered and concentrated. The residue was purified by prep. HPLC (C18, 10% to 89% acetonitrile in water (0.1% formic acid)) to compound 19 (182 mg, 44 %) as a white solid. To a stirred solution of AlCl3 (1.588 g, 11.9 mmol) in DCM (10 mL) was added methyl 2-chloro-2-oxoacetate (389 mg, 3.18 mmol) and the resulting mixture was stirred at r.t. until it became a clear solution before introduction of compound 19 (182 mg, 0.79 mmol, in 1 mL DCM). The stirring was continued at r.t. overnight. After completion of the reaction, the mixture was quenched with saturated NaHCO3 and extracted with DCM (10 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (silica gel, 0 ~ 90% ethyl acetate in petroleum ether) to provide compound 20 (58 mg, 23 %) as a yellow oil. To a stirred solution of compound 20 (58 mg, 0.18 mmol) in MeOH/H2O (1 mL/2 mL) was added NaOH (15 mg, 0.37 mmol). After stirring at r.t. for 15 min, the reaction mixture was neutralized with 1N HCl, concentrated and lyophilized to provide compound 21 (73 mg, 95 %, mixed with NaCl) as a green solid.

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:
Article; Tuyishime, Marina; Danish, Matt; Princiotto, Amy; Mankowski, Marie K.; Lawrence, Rae; Lombart, Henry-Georges; Esikov, Kirill; Berniac, Joel; Liang, Kuang; Ji, Jingjing; Ptak, Roger G.; Madani, Navid; Cocklin, Simon; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5439 – 5445;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

41253-21-8, The chemical industry reduces the impact on the environment during synthesis 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, I believe this compound will play a more active role in future production and life.

1 g of a 1,2,4-triazole sodium salt was dissolved in N,N-dimethylformamide, and the solution was cooled to 0 C., to which 570 mg of 60% sodium hydride (NaH) was then added. The reactants were stirred for 20 min, and 1.3 mL of 1-bromo-3-chloropropane was slowly added thereto. The reaction mixture was warmed to room temperature and stirred for 12 hours, followed by addition of water and extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford 600 mg (38%) of the title compound.1H NMR (CDCl3): delta 8.08 (s, 1H), 7.93 (s, 1H), 4.37-4.34 (m, 2H), 3.47-3.43 (m, 2H), and 2.35-2.29 (m, 2H)

The chemical industry reduces the impact on the environment during synthesis 41253-21-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DONG-A-PHARM. CO., LTD.; US2010/105727; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1533519-85-5, name is Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, 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 1533519-85-5, 1533519-85-5

[0278] Charge Compound 2 (1.0 kg ¡À 1%) to a reactor. Add tetrahydrofuran (6.2 kg ¡À 1% <> 7.0 L ¡À 1%) to the same reactor. Heat the mixture to a temperature between 35C and 42C. Stir the mixture for at least 10 minutes at a temperature between 35C and 42C to obtain a clear solution. Cool the reaction mixture to a temperature between 27C and 32C. [0279] Add N-bromosuccinimide (0.734 kg ¡À 1%) to the reaction mixture whilst maintaining the temperature between 27C and 32C, e.g., between 27C and 30C. Stir the mixture at a temperature between 27C and 32C, e.g., between 27C and 30C, until the reaction is complete. [0280] The reaction is considered complete when the content of Compound 2 is lower than 1.5% area by HPLC, preferentially lower than 0.2% area by HPLC. [0281] The reaction is sampled for HPLC analysis after 20 to 40 minutes of stirring for the determination of the Compound 2 content. Based on HPLC analysis, optionally add extra quantity of N-bromosuccinimide (0.105 kg ¡À 1%) while maintaining the temperature between 27C and 32C, e.g., 27C and 30C. Otherwise, continue with the stirring at a temperature between 27C and 32C, e.g., between 27C and 30C, until the reaction is complete. [0282] Cool the reaction mixture to a temperature between 2C and 7C, e.g., between 2C and 5C. Add toluene (4.33 kg ¡À 5%) to the mixture, while maintaining the temperature between 2C and 7C, e.g., between 2C and 5C. [0283] Add to the reaction mixture, over at least 10 minutes, while maintaining the temperature between 2C and 7C, e.g., between 2C and 5C, ozonated deionised water (5.0 L ¡À 5%). The addition of the ozonated deionised water is exothermic and during the addition gaseous release may occur. Stir the mixture for at least 30 minutes maintaining the temperature between 2C and 7C, e.g., between 4C and 6C. [0284] Stop stirring and allow layers to separate for at least 30 minutes. Discharge the aqueous (lower phase). Add to the organic phase, over at least 10 minutes, while maintaining the temperature between 2C and 7C, a solution previously prepared by dissolution of sodium disulfite (0.112 kg ¡À 1%) in ozonated deionised water (5.0 L ¡À 5%). The addition of the sodium disulfite solution is exothermic. During the addition gaseous release may occur. [0285] Stir the suspension for at least 30 minutes maintaining the temperature between 2C and 7C. Take a sample of the mixture. If the aqueous phase of the sample is pale yellow, conduct another wash step with sodium disulfite. If the aqueous phase of the sample is colorless then send sample for HPLC analysis. If the peak of N-bromosuccinimide is detected by HPLC then conduct another wash with sodium disulfite and repeat the HPLC analysis till the NBS is not longer detectable by HPLC. [0286] Stop stirring and allow layers to separate for at least 15 minutes. Discharge the aqueous phase (lower phase) and combine with the previous aqueous phase. Heat the organic phase comprising Compound 3 to a temperature between 18C and 25C. Add to the organic phase, maintaining the temperature between 18C and 25C, ozonated deionised water (5.0 L ¡À 5%). Stir the mixture for at least 15 minutes maintaining the temperature between 18C and 25C. Stop stirring and allow layers to separate for at least 15 minutes. Discharge the aqueous phase (lower phase). [0287] Add to the organic phase, maintaining the temperature between 18C and 25C, a solution previously prepared by dissolution of sodium bicarbonate (0.35 kg ¡À 1%) in ozonated deionised water (5.0 L ¡À 5%). Stir the mixture for at least 15 minutes maintaining the temperature between 18C and 25C. Stop stirring and allow layers to separate for at least 15 minutes. Discharge the aqueous phase (lower phase). [0288] If the pH of the discharged aqueous phase is below 8.0, repeat the wash step with sodium bicarbonate until the pH of the aqueous phase is above 8.0. [0289] Add to the organic phase, comprising Compound 3, over at least 10 minutes, while maintaining the temperature between 18C and 25 C, a solution previously prepared by dissolution of sodium hydroxide (pure) (0.1473 kg ¡À 1%) in ozonated deionised water (3.61 L ¡À 5%). [0290] Stir the mixture at a temperature between 18C and 25C for at least 2 hours until the reaction is complete. The reaction is considered complete when the peak area by HPLC of Compound 3 in the organic phase is lower than 50 mAU. If reaction is incomplete then stir the reaction mixture an extra 2 hours before re-sampling. If reaction completion is not achieved after 6 hours stirring, add extra quantity of sodium hydroxide aqueous solution and re-sample 3 hours after the addition. The reaction mixture has two phases at this point. Stop stirring and allow layers to separate for at least 30 minutes. Discharge the aqueous phase (lower phase) to a reactor or receiver. Repeat this step and combine the aqueous layers. Discharge the organic phase (upper phase) for disposal. [0291] Concentrate the aqueous phases under a vacuum at a temperatur…

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, Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; GUNIC, Esmir; GALVIN, Gabriel; WO2014/8295; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics