Triazoles

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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., Safety of 1H-1,2,3-Triazole

Example 159: Preparation of 4,5-dibromo- IH-[1, 2,3 ItriazoleTo a solution of IH-[1, 2,3]triazole (1.26 ml, 21.7 mmol) in water (10 ml) at 50C, was added bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at 50C for 1.5 hours. The white solid (2.375 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hour. More white solid (1.83 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (375 mg) was isolated via filtration and washed with water (5ml). The white solids were combined and dried to give 4,5-dibromo- IH-[1, 2,3]- triazole (4.92 g, 93% yield). M.p. 194.70C.

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; SYNGENTA LIMITED; WO2007/71900; (2007); 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. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,4-Dimethyl-1H-1,2,3-triazole

(S)-3-bromo-7-(methylsulfonyl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrrolo[2,3-b:4,5-b’]dipyridine (30 mg, 0.060 mmol) was dissolved in 1.5 mL of NMP and added l,4-dimethyl-lH-l,2,3-triazole (9.3 mg, 0.096 mmol). Tetramethylammonium acetate (12.0 mg, 0.090 mmol) and bis(triphenylphosphine)palladium(II) chloride (3.0 mg, 4.20 muetaiotaomicron) were added. Argon was bubbled through the mixture while sonicating for 5 min. The vial was capped and heated at 100 C for 33 h, then cooled and the contents of the vial were filtered. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge CI 8, 19 x 200 mm, 5-muiotatauiota particles;Mobile Phase A: 5:95 methanol: water with 10-mM NH4OAC; Mobile Phase B: 95:5 methanol: water with 10-mM ammoniumacetate; Gradient: 45-85% B over 15 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 2.8 mg (9%), and its estimated purity by LCMS analysis was 100%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH CI 8, 2.0 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 ACN:water with 10 mM Nl UOAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50 C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm. RT = 2.27, M+H = 517. Injection 2 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-mupiiota particles; Mobile Phase A: 5:95 methanol: water with 10 mM NEUOAc; Mobile Phase B: 95:5 methanol: water with 10 mM NlrUOAc; Temperature: 50 C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 0.5 mL/min; Detection: UV at 220 nm. RT = 2.27, M+H = 517. NMR (500MHz, DMSO- de) delta 8.96 (d, J=8.1 Hz, 1H), 8.76 (s, 2H), 8.05 (d, J=8.1 Hz, 1H), 7.83 (d, J=7.7 Hz, 2H), 7.33 (t, J=7.5 Hz, 2H), 7.26 (t, J=7.3 Hz, 1H), 5.93 (br. s., 1H), 4.07 (s, 3H), 3.95 – 3.83 (m, 1H), 3.82 – 3.60 (m, 2H), 3.47 – 3.36 (m, 1H), 3.31 – 3.19 (m, 1H), 2.34 (s, 3H), 1.59 – 1.49 (m, 1H), 1.49 – 1.38 (m, 1H), 1.38 – 1.22 (m, 1H), 1.16 (d, J=12.1 Hz, 1H).

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; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4928-87-4, 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. 4928-87-4 name is 1,2,4-Triazole-3-carboxylic acid, 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.

Step 5. Synthesis of ((1R,3s,5S)-3-(7-amino-6-(methylsulfonyl)-3-(6-phenyl pyridin- 3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1 ]octan-8-yl) (1H-1,2, 4-triazol-3- yl) methanoneA mixture of 1 H-1 ,2,4-triazole-3-carboxylic acid (2.8 g, 24.4 mmol), EDCI (4.7 g, 24.4 mmol), and 1-hydroxybenzotriazole (2.2 g, 16.3 mmol) in DMF (100 mL) was stirred at room temperature for 10 min. To this mixture 5-((1 R,3s,5S)-8- azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonyl)-3-(6-phenylpyridin-3-yl)pyrazolo [1 ,5- a]pyrimidin-7-amine (12.2 g, 14.8 mmol) was added followed by N,N- diisopropylethylamine (12.9 mL, 73.9 mmol). It was stirred further for 20 min at room temperature, at which time LC/MS analysis confirmed full consumption of starting material. Solvent was removed in vacuo to complete dryness. To this crude was added water (200 mL) and solids were filtered and washed with additional water (200 mL). It was then washed with MeOH (125 mL), a 1 :1 mixture of ACN and water (200 mL), ACN (100 mL) and diethyl ether (100 mL) successively to afford ((1 R,3s,5S)-3- (7-amino-6-(methylsulfonyl)-3-(6-phenyl pyridin-3-yl)pyrazolo[1 ,5-a]pyrimidin-5-yl)-8- azabicyclo[3.2.1]octan-8-yl)(1 H-1 ,2,4-triazol-3-yl) methanone (7.5 g).; Step 6. Synthesis of ((1R,3s,5S)-3-(7-amino-6-(methylsulfonyl)-3-(6-phenyl pyridin- 3-yl) pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1 ]octan-8-yl)(1H-1,2, 4-triazol-3- yl) methanone hydrochlorideTo a suspension of ((1 R,3s,5S)-3-(7-amino-6-(methylsulfonyl)-3-(6-phenyl pyridin-3-yl) pyrazolo[1 ,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]octan-8-yl)(1 H-1 ,2,4- triazol-3-yl) methanone (8g, 14.1 mmol) in DCM (350 mL) and MeOH (100 mL) was added 4M HCI in 1 ,4-dioxane (14.1 mL, 56.2 mmol). It was stirred further for 10 min at room temperature during which time solution became clear. Solvent was removed in vacuo until solids were precipitate out. To this crude was added diethyl ether (200 mL) and solids were filtered and washed with additional diethyl ether (800 mL).Solids were redissolved in a 1 :1 mixture of ACN and water and lyophilized to get the desired ((1 R,3s,5S)-3-(7-amino-6-(methyl sulfonyl)-3-(6-phenylpyridin-3- yl)pyrazolo[1 ,5-a] pyrimidin-5-yl)-8-azabicyclo [3.2.1]octan-8-yl)(1 H-1 ,2,4-triazol-3- yl)methanone as an HCI salt (8.5 g).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; SCHERING CORPORATION; SIDDIQUI, M. Arshad; NAN, Yang; PATEL, Mehul, F.; REDDY, Panduranga Adulla P.; MANSOOR, Umar Faruk; MENG, Zhaoyang; VITHARANA, Lalanthi Dilrukshi; ZHAO, Lianyun; MANDAL, Amit, K.; LIU, Duan; TANG, Shuyi; MCRINER, Andrew; BELANGER, David, B.; CURRAN, Patrick, J.; DAI, Chaoyang; ANGELES, Angie, R.; YANG, Liping; DANIELS, Matthew Hersh; WO2011/90935; (2011); 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. 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, A new synthetic method of this compound is introduced below., Recommanded Product: (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol

To a solution of (1-methyl-1 H-1 ,2,4-triazol-3-yl)methanol (489 mg, compound D24) in dry DCM (0.6 ml) are added tetrabromomethane (1 .87 g) and triphenylphosphane (1.48 g). The mixture is stirred for 1 h at RT to give 3-(bromomethyl)-1-methyl-1 H-1 ,2,4-triazole. The reaction mixture is directly used in step 2.

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; NYCOMED GMBH; FLOCKERZI, Dieter; STENGEL, Thomas; MANN, Alexander; OHMER, Harald; KAUTZ, Ulrich; WEINBRENNER, Steffen; FISCHER, Stefan; ZITT, Christof; HATZELMANN, Armin; DUNKERN, Torsten; HESSLINGER, Christian; MAIER, Thomas; TENOR, Hermann; BRAUN, Clemens; KUeLZER, Raimund; MARX, Degenhard; WO2011/73231; (2011); 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. 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, A new synthetic method of this compound is introduced below., Safety of 5-Phenyl-1H-1,2,4-triazol-3-amine

STEP E; A reaction mixture of compound 35-4 (28.3 mg, 0.1 mmol) and 3-phenyl-1H- 1 ,2,4-triazol-5-amine (16 mg, 0.1 mmol) in ethanol was stirred at 80 0C for overnight. The product was purified using reverse phase HPLC.

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; SCHERING CORPORATION; SHIPPS, JR., Gerald, W.; CHENG, Cliff, C.; HUANG, Xiaohua; ACHAB, Abdelghani, Abe; ORTH, Peter; VOIGT, Johannes, H.; SOUCY, Kyle, Ann; WO2010/56631; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 40253-47-2, 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. 40253-47-2, name is Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

A mixture of ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate (1.0 g, 6.45 mmol) and sodium hydroxide (1.702 mL, 32.2 mmol) in tetrahydrofuran (30 mL) was stirred at ambient temperature for 16 hours. Volatiles were removed, and the residue was acidified with 1 N HCl solution. Water was removed under high vacuum, and the crude residue was purified by HPLC (0~70% acetonitrile in 0.1% trifluoroacetic acid/water on Phenomenex C1810 mum (250 mm ¡Á 50 mm) column at a flowrate of 50 mL/minute) to give 460 mg of the title compound as a white solid.

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, Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 22300-52-3, name is 4,5-Dibromo-2H-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 22300-52-3, Quality Control of 4,5-Dibromo-2H-1,2,3-triazole

3- Fluoro-4-nitrotoluene (1367 g, 1 eq.), 4,5-dibromo-2/-/-1 ,2,3-triazole (1999 g, 1 eq.), K2C03 (1340 g, 1.1 eq.) and DMF (1 1 L) is heated to 75 C for 15 h. The reaction mixture is cooled to 22 C and treated with water (18 L). The resulting suspension is filtered, washed with water (4 L). The product is washed with isopropanol (5 L), and dried under reduced pressure to yield a white solid. Yield: 281 1 g, 88%. Purity: 100% a/a (LC-MS method 2). 1H NMR (400 MHz, DMSO) <5: 8.10 (d, J = 8.3 Hz, 1 H), 7.86 (d, J = 1.0 Hz, 1 H), 7.66 (dd, J1 = 0.9 Hz, J2 = 8.3 Hz, 1 H), 2.51 (s, 3 H). 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; IDORSIA PHARMACEUTICALS LTD; DOeRRWAeCHTER, Patric; SCHMIDT, Gunther; (48 pag.)WO2018/202689; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-70-2, The chemical industry reduces the impact on the environment during synthesis 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

G. (2S,4S)-5-Biphenyl-4-yl-2-hydroxymethyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid 1-isopropoxycarbonyloxy-ethyl ester (R7=-CH(CH3)OCOO-CH(CH3)2) (2S,4S)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-pentanoic acid (50 mg, 120 mumol, 1.0 eq.), DMA (1 mL), DIPEA (0.13 mL) and 1-chloroethyl isopropyl carbonate (83 mg, 0.5 mmol, 4.0 eq.) were combined. The reaction vessel was capped and microwaved at 80 C. for 2 hours. The mixture was dried under vacuum, dissolved in MeCN (2 mL), and combined with 4 M of HCl in dioxane (500 muL). The resulting mixture was stirred at room temperature for 30 minutes. The precipitate was filtered and discarded, and the filtrate containing the intermediate was concentrated down and submitted to the next step. 1,2,3-Triazole-4-carboxylic acid (14 mg, 120 mumol, 0.5 eq.) and HATU (48 mg, 120 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 (44 muL) and the intermediate from last step. The mixture was stirred for 5 minutes. The reaction was quenched with water and the product dried under vacuum. The product was then purified by preparative HPLC to yield the title compound (6 mg; purity 95%). MS m/z [M+H]+ calc’d for C27H32N4O7, 525.23. found 525.4.

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

Related Products of 60166-43-0,Some common heterocyclic compound, 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, molecular formula is C4H7N3, 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.

In a 75 mL pressure vessel equipped with a magnetic stirring bar was added (75% purity, yellow foam as the title compound. NMR (500MHz, DMSO-c e) delta 8.71 – 8.62 (m, 2H), 8.21 (t, J=7.3 Hz, 1H), 7.46 (d, J=8.1 Hz, 1H), 7.41 – 7.24 (m, 2H), 7.12 (t, J=9.4 Hz, 1H), 6.18 (br. s., 1H), 4.01 (br. s., 3H), 3.93 – 3.82 (m, 2H), 3.74 (d, J=9.9 Hz, 1H), 3.53 (d, J=8.8 Hz, 1H), 3.49 – 3.36 (m, 1H), 3.30 – 3.12 (m, 1H), 2.29 (s, 3H), 1.66 (d, J=1 1.7 Hz, 1H), 1.53 – 1.39 (m, 1H), 1.39 – 1.26 (m, 1H), 0.96 (d, J=12.5 Hz, 1H). LC/MS (M+H) = 491.4; HPLC conditions: Rt = 3.30 min (Phenomenex LUNA C 18 2 x 50 mm (4 min grad) eluting with 5-95% aq ACN containing lOmM NH4OAC, 0.8 mL/min, monitoring at 254 nm); Temperature: 40C).

The synthetic route of 60166-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

Step 2: To a clean 500 mL flask were added to following reagents: compound J3 (300 mg, 0.82 mmol), 3-(2H-l,2,3-triazol-2-yl)aniline (compound J4, 261 mg, 1.63 mmol), fine-powder cesium carbonate (802 mg, 2.46 mmol), Q-Phos (l,2,3,4,5-pentaphenyl-l ‘-(di- tert-butylphosphino)ferrocene) (58 mg, 0.082 mmol; Aldrich No.675784) and Pd(dba)2 (bis(dibenzylideneacetone)palladium(O)) (92 mg, 0.16 mmol; Aldrich No.227994). To the mixture was then added 30 mL toluene. The resulting slurry was degassed using argon stream gently for 3 min. It was then sent to 110C bath with an air-cooled condenser on top and stirred under argon for overnight. The mixture was then cooled to RT and concentrated on rotovap to remove all the solvent. To the residue were added 300 mL EtOAc and 100 mL water. After vigorously stirring for 15-30 min, the organic phase was separated, and the aq phase and the black junks between org and aq phases were all discarded. The EtOAc phase was then washed with brine twice. The organic phase was dried over MgS04, concentrated and subjected to flash column with 0%-15% EtOAc in DCM to isolate the desired product, compound J5.

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

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