Day: November 23, 2020

The chemical industry reduces the impact on the environment during synthesis 288-36-8, name is 1H-1,2,3-Triazole, I believe this compound will play a more active role in future production and life. 288-36-8

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 ¡Á 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

The chemical industry reduces the impact on the environment during synthesis 288-36-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
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. 288-36-8 name is 1H-1,2,3-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. 288-36-8

To a solution of 2-iodobenzoic acid (3.0 g, 12.1 mmol) in DMF was added 1,2,3- triazole (1.5 g, 21.7 mmol), Cs2CO3 (7.1 g, 21.7 mmol), Cul (114 mg, 0.6 mmol), and trans-N,N?dimethylcyclohexane- 1 ,2-diamine (310 mg, 2.2 mmol). After heating at 120 C for 10 mm in amicrowave reactor, the mixture was cooled to room temperature, diluted with EtOAc, and filtered through Celite. The filtrate was concentrated in vacuo and the crude residue was purified by silica gel chromatography (MeOH in DCM with 0.1% AcOH) to give Intermediate N as the faster eluting isomer. ?H NMR (DMSO-d6, 500MHz) oe 13.05 (brs, 1 H), 8.12 (s, 2H), 7.8 1-7.52 (m, 4H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; ROECKER, Anthony, J.; (0 pag.)WO2016/85783; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4314-22-1, name is 2-(1H-1,2,3-Triazol-1-yl)acetic acid, 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. 4314-22-1

To a stirred mixture of 5 (65 mg, 0.173 mmol), 1 – 1 ,2,3-triazoleacetic acid (6, 22 mg, 0.173 mmol), and Hunig’s base (0.091 mL, 0.522 mmol) in DMF (2 ml) was added HATU (66 mg, 0.174 mmol) and the reaction mixture was stirred for 30 min. The crude mixture was directly purified by prep. HPLC to give 7 (39 mg, 46%). -NMR (400MHz, d6-DMSO): 513.0 (s, IH), 8.34 (bs, IH), 8.16-8.1 1 (m, 2H), 8.00-7.95 (m, 2H), 7.71 (s, IH), 7.55-7.42 (m, 2H), 7.19 (q, IH), 5.51-5.43 (2s, 2H), 4.86-4.83 (m, 2H), 3.81-3.52 (m, 4H), 3.13-3.12 (2s, 3H), 3.04-2.97 (2s, 3H), 2.64-2.63 (2s, 3H). MS (EI) for C24H27N, ,0, found 486 (MH+).

Statistics shows that 4314-22-1 is playing an increasingly important role. we look forward to future research findings about 2-(1H-1,2,3-Triazol-1-yl)acetic acid.

Reference:
Patent; EXELIXIS, INC.; LEAHY, James, William; WO2012/37204; (2012); 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. 16681-65-5 name is 1-Methyl-1H-1,2,3-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. 16681-65-5

The title compound was prepared according to No. WO2008 / 135826 International Patent Application Publication. In 1-methyl -1H-1,2,3- triazole (1.0g, 12.0 mmol, prepared according to International Patent Application No. 2008098104) 50 mL 2-neck flask containing, by the addition of THF (45 mL) , colorless solution was cooled to -40 . Then, by adding dropwise the (2.5 M, 4.8 mL, 12.0 mmol in hexane) n-BuLi, to give a dark reddish brown viscous solution. The mixture was stirred for 45 minutes at -30 to -20 in the following, was introduced into a pure DMF (3mL, 38.5 mmol) at -10 . The mixture was allowed to warm to room temperature, after stirring for 60 minutes, poured into water. Extract the aqueous portion with EtOAc (4 ¡Á 50 mL), the combined organics washed with brine, dried with MgSO4, filtered, and concentrated. The aqueous portion was extracted with DCM (3 ¡Á 50 mL) station, and dried as described above. The combined organics were concentrated to give a light brown oil The UV activity much higher than the starting material. DCM-25% CH3CN, according to TLC or of from 25% EtOAc-DCM, showed the product has a slightly higher Rf than the starting material. (With 100% DCM, 25% CH3CN-DCM increased) by silica gel chromatography on to give the title compound as a colorless oil.

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

Reference:
Patent; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

41253-21-8, Adding a certain compound to certain chemical reactions, such as: 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, 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 41253-21-8.

5-Fluoro-2-(lH-l,2,4-triazol-l~yl)benzonitrile. A suspension of 2,5- diflurobenzonitrile (4.5 g, 32.35 mmol) and 1,2,4-triazole sodium salt (3.6 g, 40 mmol) in dimethylformamide (40 mL) was heated at 80 0C for 15 h. The reaction mixture was then cooled, diluted with CH2Cl2 (200 mL), washed with water (3 X 30 mL) and brine (30 mL), then dried (Na2SO4), filtered and concentrated to give a white solid which was purified by flash column chromatography (SiO2) using 1 : 1 to 3:1 ethyl acetate/Hexanes to afford the title compound (2.98 g, 49% yield) as a white powder. 1H NMR (500 MHz, CDCl3) delta: 8.70 (IH, s), 8.18 (IH, s), 7.76 (IH, dd, J = 9.0, 4.8 Hz), 7.55 (IH, dd, J = 7.3, 2.8 Hz), 7.51-7.47 (IH, m). LCMS (M+H) calcd for C9H6FN4: 189.17; found: 189.10.

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 41253-21-8

3-Fluoro-2-l,2,4-triazol-l-yl-benzoniti”ile. A mixture of 2,3- difluorobenzylnitrile (2.27 g, 16.3 mmol) and triazole sodium salt (1.33 g, 14.8 mmol) in tetrahydrofuran (5 mL) and dimethylformamide (10 mL) was stirred at 85 C for 4 h. After concentration, the residue was purified by flash chromatography (SiO2) eluting with 25%-50% ethyl acetate/hexane. The isolated product was recrystallized from hot ethyl acetate/hexane to give the title compound as white needles (1.51 g, 54% yield). 1H-NMR (500 MHz, CDCl3) delta ppm: 8.50 (IH, d, J= 2.4 Hz), 8.25 (IH, s), 7.69-7.67 (IH, m), 7.60-7.57 (2H, m). LCMS [M+H]+ calcd for C9H6N4F: 189.16; found: 189.14.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41253-21-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); 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

Example A32 a) Preparation of intermediate 84 CuI (1.71 g, 8.9 mmol) and N,7V-dimethylethylenediamine (1.91 ml, 17.92 mmol) were added to a mixture of 2-amino-5-iodopyridine (5.03 g, 22.4 mmol), 3-methyl- IH- 1,2,4- triazole (2.42 g, 29.1 mmol), and Cs2CO3 (14.60 g, 44.81 mmol) in DMF (40 ml). The r.m. was heated at 110 0C for 7 h., the r.m. was cooled, EtOAc was added and the mixure was washed with water. The water layer was extracted 5 times with EtOAc. The combined organic layers were dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by RP preparative EtaPLC [RP Shandon Etayperprep Cl 8 BDS (8 mum, 250 g, LD. 5 cm); mobile phase: a gradient of (0.25 % NH4HCO3 solution in water)/MeOH/CH3CN]. The product fractions were collected and the solvent was evaporated. Yield: 1.5 g of intermediate 84 (38 %).

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; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; BISCHOFF, Francois Paul; ZHUANG, Wei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; MACDONALD, Gregor, James; OEHLRICH, Daniel; WO2010/94647; (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. 288-36-8 name is 1H-1,2,3-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. 288-36-8

To a 50 mL round-bottomed flask equipped with a magnetic stirbar was added 1-H-1,2,3-triazole (0.192 g, 2.78 mmol) and DMF (10 mL) and then cooled to 0 C. while stirring. Then, sodium hydride (60% dispersion in mineral oil) (0.133 g, 3.33 mmol) is added to the reaction mixture and was slowly allowed to warm to ambient temperature. Then, 1-iodo-4 pentyne (0.647 g, 3.33 mmol) was added dropwise. The reaction mixture was then heated to 80 C. and allowed to stir for 2.5 hours. Water (20 mL) was then added to the reaction mixture and then extracted with ethyl acetate (2*20 mL). The organic phase was dried with sodium sulfate and concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane) to produce 1-Pent-4-ynyl-1H-[1,2,3]triazole (0.349 g, 93%) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 7.67 (s, 1H), delta 7.59 (s, 1H), delta 4.53 (t, 2H), delta 2.20 (t, 2H), delta 2.17 (m, 2H), delta 2.04 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) delta 133.9, 123.9, 82.2, 70.4, 48.7, 28.9. 15.7 ppm; HRMS (ESI) calcd for C7H10N3 (M+) 136.0869, found 136.0866.

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

Reference:
Patent; North Carolina State University; US2009/263438; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, 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 4928-87-4. 4928-87-4

To a reaction of H-, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and 3- methoxybenzylamine (0.28 mL, 2.2 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- Dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into iced water and extracted with DCM (2 x 50 mL). The DCM phase was washed with ice cold water (2 x 100 mL). The DCM phase was dried over anhydrous Na2S04, concentrated under reduced pressure and chromatographed on silica gel using MeOH and DCM (2:98) as eluents to get the desired amide 7 (170.9 mg, 37 % yield) as a white solid compound. -NMR (400 MHz, DMSO-de): <514.76-14.65 (m, 1H), 9.15 (br s, 1H), 8.48 (br s, 1H), 7.23 (t, J= 8 Hz, 1H), 6.90-6.88 (m, 2H), 6.82-6.80 (m, 1H), 4.43 (d, J= 6 Hz, 2H), 3.73 (s, 3H) ppm. MH+ = 233.2 m/z. 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 1,2,4-Triazole-3-carboxylic acid. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 7411-23-6, name is 3,5-Dibromo-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 7411-23-6. 7411-23-6

A suspension of 3,5-dibromo-4H-1,2,4-triazole (453.7 mg, 2 mmol) 2-fluorophenylboronic acid (420 mg, 3 mmol) copper(II) acetate (363 mg, 2 mmol) sodium carbonate (318 mg, 3 mmol) and pyridine (0.24 mL, 3 mmol) in toluene (2 mL) was heated at 70 C overnight. The reaction mixture was cooled to r.t. and filtered through celite (eluting with EtOAc). The filtrate was washed with sat. aq. NH4Cl solution (15 mL) and water (10 mL), dried and concentrated. The crude product was purified by flash column chromatography (SiO2) eluting with 20-50% EtOAc in Pet. Ether to give 3,5-dibromo-4-(2- fluorophenyl)-1,2,4-triazole (98 mg, 0.31 mmol, 15% yield) as a colourless oil, which crystallised on standing. Regioisomer confirmed by DEPT-quat expt. LC-MS (ES+, Method D): 5.61 min, m/z 321.7 [M+H]+.1H NMR (400 MHz, CDCl3): delta 7.57 (m, 1H), 7.46 (m, 1H), 7.36-7.32 (m, 1H), 7.32-7.28 (m, 1H).

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 3,5-Dibromo-1H-1,2,4-triazole.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics