Day: December 4, 2020

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

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

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

The chemical industry reduces the impact on the environment during synthesis 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life. 7170-01-6

Example 4 Synthesis of SC11 To a stirred solution of benzoic acid (116 mg, 0.94 mmol) in DCM (3 mL) were added compound 7 (200 mg, 0.94 mmol), TEA (0.4 mL, 2.82 mmol) and HBTU (536 mg, 1.39 mmol). The resulting mixture was stirred at r.t. overnight before quenched with sat. NaHCO3. The layers were separated and the aqueous layer was extracted with DCM (10 mL*3). The combined organic layers was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 0?50% ethyl acetate in petroleum ether with 0.5% TEA) to provide compound 8 (164 mg, 55%) as a yellow solid. Compound 9 (303 mg, 100%) was obtained as a yellow oil by treating compound 8 (345 mg, 1.09 mmol) with 4N HCl/Dioxane (3 mL). 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 100 C. 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*20 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*35 ml). Combined extracts were dried over Na2SO4 and concentrated to afford compound 14 (0.8 g, 40%) as light-yellow solid At 143 C., to molten 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*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 sat. NaHCO3 and extracted with DCM (10 mL*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. Compound 21 (55 mg, 0.18 mmol) in DMF and compound 9 (59 mg, 0.27 mmol) were added to DIPEA (0.28 mL, 1.63 mmol) and DEPBT (325 mg, 1.09 mmol). After stirring at r.t. overnight, the reaction mixture was concentrated to remove DMF under the reduced pressure. The residue was partitioned between with EA (10 mL) and sat. NaHCO3 (10 mL). The layers were separated and the aqueous layer was extracted with EA (10 mL*2). The combined organic layers was dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative HPLC to give compound SC11 (22 mg, 24%).

The chemical industry reduces the impact on the environment during synthesis 7170-01-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Drexel University; Cocklin, Simon; (79 pag.)US2016/214998; (2016); 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. 7170-01-6

To a vial charged with racemic 5-(benzofuran-2-yl)-3 – (5-bromo-6-methoxypyridin-2-yl)-5,6-dthydro-4H- 1 ,2,4-oxadiazine (110 mg, 0.28 mmol, 1.0 equiv.), 3-methyl-1H-1,2,4-triazole (47.1 mg, 0.57 mmol, 2.0 equiv.), and K3P04 (120 mg, 0.57 mmol, 2.0 equiv.) under N2 atmosphere was added degassed 4:1 PhMe:dioxane solvent mixture (2.00 mL). To a second vial charged with Pd2(dba)3 (20.8 mg, 0.02 mmol, 8.0 mol%) and Me4-di-t-BuXPhos (CAS 857356-94-6, 21.8 mg, 0.05 mmol, 16 mol%) under N2 atmosphere was added degassed 4:1 PhMe:dioxane solvent mixture (0.83 mL). This mixture was stirred for 3 minutes at 120 C to provide a dark red solution which was cooled to RT and transferred to the first vial. The reaction was degassed by bubbling with N2 for 5 minutes and then sealed. The reaction mixture was stirred at 120 C for 16 h. The reaction was cooled to RT and filtered through a pad of celite which was washed thoroughly with EtOAc. The filtrate was concentrated, and the residue was purified by normal phase chromatography on silica (0-5% MeOH / DCM) to afford 5-(Benzofuran-2-yl)-3-(6-methoxy-5-(3-methyl-1H- 1,2,4-triazol-1-yl)pyridin-2-yl)-5,6-dthydro-4H-1,2,4-oxadiazine (77.4 mg, 70%) as an off- white solid.

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 PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); 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. 7170-01-6 name is 3-Methyl-1H-1,2,4-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. 7170-01-6

Step A. 2-Chloro-4-(3 -methyl-i H-i ,2,4-triazol- 1 -yl)benzaldehydeTo a solution of 2-chloro-4-fluorobenzaldehyde (95 mmol, 15 g) and 3-methyl-1H-i,2,4-triazole(114 mmol, 9.4 g) in CH3CN (300 mL) was added K2C03 (142 mmol, 20 g) and stirred at 60 C.After 24 h, the reaction mixture was added water and extracted with EtOAc. The organic extracts washed with saturated aq. NaC1, dried over Na2SO4, and filtered and concentrated in vacuo. The crude was purified by column chromatography (heptane :EtOAc = 20:80-10:90) to give the title compound. MS (ESI) mlz = 222, 224 (M+H)?H NMR (300 MHz, CDC13) 5 (ppm): 10.45 (1H, s), 8.55 (1H, s), 8.06 (1H, d, J 8.6 Hz), 7.87(1H, d, J= 2.1 Hz), 7.68 (1H, dd, J 8.6, 2.1 Hz), 2.51 (3H, s).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SAKURADA, Isao; HIRABAYASHI, Tomokazu; MAEDA, Yoshitaka; NAGASUE, Hiroshi; MIZUNO, Takashi; XU, Jiayi; ZHANG, Ting; SMITH, Cameron; PARKER, Dann; WO2015/160636; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

252742-72-6, The chemical industry reduces the impact on the environment during synthesis 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, I believe this compound will play a more active role in future production and life.

13.35 g (100 mmol) of 3-chloromethyl-1, 2, 4-triazolin-5-one, 64.628 (120 mmol) tetrabenzyl pyrophosphate and 50 ml of THF were added to the reaction flask, stirred well, cooled down to -5 ¡ã C, 24.69 g (220 mmol) of potassium t-butoxide was added, after the addition, continue to stir the reaction, TLC monitor the reaction end point. 300 ml of saturated sodium bicarbonate solution and 300 ml of isopropyl ether were added the reaction solution, stirred for 15 min, and dispense, the organic phase was washed with saturated brine until neutral, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to dryness, dried in vacuo to give 33.86 g white solid, yield 86percent.

The chemical industry reduces the impact on the environment during synthesis 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong New Age Pharmaceutical Co., Ltd.; Zhao Zhiquan; Bai Wenqin; Wang Youguo; Sun Xiuling; Dai Shaogang; (7 pag.)CN104650143; (2018); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 61-82-5, name is 1H-1,2,4-Triazol-5-amine, 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 61-82-5. 61-82-5

General procedure: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

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 1H-1,2,4-Triazol-5-amine.

Reference:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

956317-36-5, A common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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.

(S)-(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)(5-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)-6-azaspiro[2.5]octan-6-yl)methanone 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (1 eq; prepared according to WO 2008147518), HOBT (1 eq) and EDCI.HCl (1.5 eq) dissolved in dichloromethane (5 ml/mmol) were stirred at 25 C. for 0.5-2 hours, then intermediate 2 (1 eq) dissolved in dichloromethane was added. After 18 hours the mixture was poured in an aqueous saturated solution of NaHCO3 and extracted with dichloromethane. The crude was purified by silica gel column chromatography (DCM to DCM/MeOH=9/1) to obtain the title compound with yield of 52%. 1HNMR (CDCl3) delta ppm 8.22-8.38 (m, 1H), 7.94-8.14 (m, 1H), 7.79-7.86 (m, 1H), 7.69 (m, 1H), 7.50-7.62 (m, 1H), 7.28-7.37 (m, 1H), 7.0-7.24 (m, 1H), 6.48-6.66 (m, 1H), 5.20 (m, 1H), 4.34-4.84 (m, 1H), 3.89-4.0 (m, 1H), 3.65-3.75 (m, 1H), 3.21-3.44 (m, 2H), 3.01-3.11 (m, 1H), 2.26-2.46 (m, 3H), 1.89-2.17 (m, 1H), 1.02-1.28 (m, 1H), 0.19-0.63 (m, 4H) MS=ESI+m/z 439 [M+H]+

The synthetic route of 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; Stasi, Luigi Piero; Rovati, Lucio; US2013/310400; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, Adding some certain compound to certain chemical reactions, such as: 288-36-8, name is 1H-1,2,3-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 288-36-8.

A solution of lH-l ,2,3-triazole (1.0 g, 14.5 mmol), methyl iodide (3.1 g, 21.7 mmol) and K2C03 (4.0 g, 28.9 mmol) in THF (15 mL) was stirred at room temperature for 3 hours. EtOAc (20 mL) and H20 (10 mL) were added, separated. The solvent was concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 10% MeOH/DCM to afford 1 -methyl- lH-l ,2,3-triazole (860 mg, 10.4 mmol, 71 % yield) as yellow oil.

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 288-36-8.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Jinhua; DING, Charles Z.; DRAGOVICH, Peter; FAUBER, Benjamin; GAO, Zhenting; LABADIE, Sharada; LAI, Kwong Wah; PURKEY, Hans Edward; ROBARGE, Kirk; WEI, Binqing; ZHOU, Aihe; WO2015/140133; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics