Category: Triazoles

Related Products of 7343-33-1, These common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, 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.

Example 5 Preparation of 3-bromo-1-(4-(trifluoromethoxy)Phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with potassium phosphate (K3PO4, 7.74 g, 36.5 mmol), CuI (0.165 g, 0.868 mmol), and 3-bromo-1H-1,2,4-triazole (2.83 g, 19.10 mmol). The flask was evacuated/backfilled with N2 (3*). DMF (34.7 mL) was added, followed by trans-(1R,2R)-N,N’-bismethyl-1,2-cyclohexane diamine (0.274 mL, 1.736 mmol) and 1-iodo-4-(trifluoromethoxy)benzene (5 g, 17.36 mmol). The solution was heated to 110¡ã C. After 48 h, the reaction mixture was cooled to RT, diluted with EtOAc and filtered through Celite?. The filtrate was washed with water (100 mL) containing HCl (1 M, 10 mL). The organics were separated, and the aqueous phase was further extracted with EtOAc (3*). The organics were combined, dried with sodium sulfate, and concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as a tan solid (1.86 g, 34percent): 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta-58.04; EIMS m/z 307 ([M]+).

The synthetic route of 7343-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CREEMER, Lawrence C.; US2014/275504; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

5-chloro-2-[(5R)-hexahydro-5-methyl-i H-i ,4-di-azepin-i -yl]benzoxazole (75 mmol) was dissolved in N,NDimethylformamide (75 ml), then cooled to 0 to 5 C., and added with 5-methyl-2-(2H- 1 ,2,3-triazole-2-yl)benzoic acid (79 mmol), HOAt (82.8 mmol), EDCI (82.8 mmol) and triethylamine (188 mmol); then the mixture was warmed naturally and stirred at room temperature overnight. 10 mass % citric acid solution was added, and the aqueous phase separated was extracted with ethyl acetate. The resulted organic phase was washed with 5% sodium carbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtrated and dried by evaporation, to give suvorexant with a yield of 97%, and the cc value is 99.8%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, its application will become more common.

Reference:
Patent; Zhejiang Huahai Pharmaceutical Co., Ltd.; Shanghai Aobo Pharmtech, Inc., Ltd.; Lin, Jianping; Guo, Xiaowen; Gao, Xiaofei; Huang, Chao; Guo, Yuanbing; Tao, Anping; Huang, Luning; Gu, Hong; (15 pag.)US2019/40052; (2019); 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.

General procedure: To a mixture of dimedone (1 mmol), aldehyde (1 mmol), 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1 mmol)and nano-SiO2 (15 mol %) in the acetonitrile (5 mL) was stirred for appropriate time (Table 2) at 25-30 C. After the completion of the reaction as indicated by TLC, dichloromethane (CH2Cl2) was added to the solidified mixture and the insoluble catalyst was separated by filtration. Evaporation of the solvent from the filtrate and recrystallization of the solid residue from hot ethanol afforded the pure products in high yields.

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:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Journal of the Iranian Chemical Society; vol. 12; 5; (2015); p. 743 – 749;,
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

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

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. 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

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

Application of 3641-13-2, 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. 3641-13-2 name is 5-Amino-4H-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.

General procedure: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., SDS of cas: 288-36-8

A suspension of 2-fluoro-6-iodobenzoic acid (300 mg, 1 .1 mmol), (1 R,2R)-N,N- dimethylcyclohexane-1 ,2-diamine (32 mg, 0.23 mmol), Cs2C03 (735 mg, 2.3 mmol), 1 H- 1 ,2,3-triazole (0.13 mL, 2.3 mmol), water (0.01 mL) in 1 ,4-dioxane (5 mL) was degassed under nitrogen for 10 mins. Cul (10.7 mg, 0.06 mmol) was added and the mixture was further degassed under nitrogen for 10 mins. The pressure tube was sealed and the mixture was heated to 100 for 18 hrs. After cooling, the reaction mixture was quenched with 13%wt NaCI in 2.5M hydrochloric acid (50 mL) and extracted with EtOAc. The combined organics were dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on the Biotage Isolera Four (25 g column, 0 to 75% (10% AcOH in EtOAc) in heptane) to afford the title compound as an oil (140 mg). 1H NMR (250 MHz, MeOD) 7.94 (s, 2 H), 7.80 (m, 1 H), 7.62 (m, 1 H), 7.29 (m, 1 H).

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4X DISCOVERY LIMITED; BLANEY, Emma Louise; MARTIN, Barrie Phillip; NOWAK, Thorsten; WATSON, Martin John; (212 pag.)WO2016/34882; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics