Category: Triazoles

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 7170-01-6

To a mixture of 3-methyl- lH- l,2,4-triazole (330 mg, 3.97 mmol), 5-chloro-2-fluoro- benzaldehyde (425 mg, 2.68 mmol) in DMSO (5.0 mL) is added K2C03 (725 mg, 5.25 mmol). The reaction mixture is stirred at 100 C for 2 hours. The reaction mixture is allowed to cool to room temperature, diluted with CH2C12 (100 mL), and washed with H20 (75 mL x2). The organic layer is dried with Na2S04 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 5% MeOH in EtOAc as the eluent to afford an impure mixture of 5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-benzaldehyde plus regiosiomer (270 mg).To a mixture of 4-(2-amino-pyrimidin-5-yl)-Nl-ieri-butyl-benzene-l,2-diamine (270 mg, 1.05 mmol) and impure mixture of 5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-benzaldehyde plus regiosiomer (270 mg) in DMF (15.0 mL) is added Oxone (650 mg, 1.06 mmol) in H20 (5.0 mL). The reaction mixture is stirred at room temperature for 1.5 hours and then quenched with saturated sodium thiosulfate aq. (25 mL). The quenched reaction mixture is extracted with EtOAc (25 mL x2) and the combined organic layers are washed with H20 (50 mL x2), dried with Na2S04 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 5% MeOH in CH2C12 as the eluent to afford an impure mixture of 5-(2-amino- pyrimidin-5-yl)- l-ieri-butyl-2-[5-chloro-2-(3-methyl- l,2,4-triazol-l-yl)-phenyl]-2,3- dihydro-lH-benzimidazol-2-ol plus regiosiomer (25 mg).

We’ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 3-Methyl-1H-1,2,4-triazole ,and how the biochemistry of the body works.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; HAO, Ming-Hong; LIU, Weimin; LO, Ho-Yin; LOKE, Pui Leng; MAN, Chuk, Chui; MORWICK, Tina, Marie; NEMOTO, Peter, Allen; TAKAHASHI, Hidenori; TYE, Heather; WU, Lifen; WO2011/68821; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 288-88-0, name is 1H-1,2,4-Triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

To a stirred solution of 4-fluro benzaldehyde (1.0 g, 0.8 mmol) in dry DMF (5 mL), 1 H-1 ,2,4-triazole (660 mg, 0.9 mmol) and K2CO3 (2.2 g, 1.6 mmol) were added at RT and the resulting mixture was stirred overnight at 1 10 C. After completion of reaction, ice water (2 mL) was added and the mixture was extracted with EtOAc (2 x 20 ml_). The combined organic layer was washed with brine (2 ml_), dried over Na2S04 and concentrated under vacuum. The resulting product was used in next step without further purification. Yield: 46% (610 mg, white solid). LCMS: (Method A) 174.1 (M+H), Rt.1.27 min, 67.51 % (Max).

If you are hungry for even more, make sure to check my other article about 288-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; RAKESH, Paul; (338 pag.)WO2020/39027; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 4928-87-4, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, molecular formula is C3H3N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

General procedure: The tail group amines Ar-NH2 (Ar a-d) (19.5 mmol,1.1 equiv) were added to a stirring solution of 1,2,4-triazole-3-carboxylic acid 12 (2.00 g, 17.7 mmol, 1.0 equiv) in dry DMF(30 mL) at room temperature. After 5 min, TBTU (6.0 g, 18.6 mmol,1.0 equiv) and DIPEA (11.0 mL, 61.9 mmol, 3.5 equiv) were added insequence. The resulting solution was stirred at room temperaturefor 16 h. After completion of the reaction, as indicated by TLC, DMFwas removed by rotary evaporation at 30 torr and 70 C. The crudematerial was purified by methods described in each individualentry.

The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about 1,2,4-Triazole-3-carboxylic acid is helpful to your research.

Reference:
Article; Chakraborty, Amarraj; Dou, Yali; Gibbons, Garrett S.; Grigsby, Sierrah M.; Lee, Young-Tae; Liao, Chenzhong; Mathew, Bini; Moukha-Chafiq, Omar; Nikolovska-Coleska, Zaneta; Pathak, Vibha; Reynolds, Robert C.; Schuerer, Stephan C.; Snowden, Timothy S.; Umeano, Afoma C.; European Journal of Medicinal Chemistry; vol. 189; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 7411-23-6

To a solution of 3,5-dibromo-lh-l,2,4-triazole (150.0 g, 661.2 mmol) in tetrahydrofuran (1500 mL) was slowly added p-toluenesulfonic acid (17.1 g, 99.2 mmol), followed by 3,4-dihydro-2h-pyran (166.9 g, 1983.6 mmol) at 0 C. After addition, the reaction mixture was heated at 70 C for 3 h and concentrated under reduced pressure. The residue was poured into water (500 mL) and adjusted to pH = 9 by addition of saturated aqueous sodium bicarbonate. The resulting mixture was extracted with ethyl acetate (3 x 400 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduce pressure. The resulting crude product was washed with methanol (2 x 50 mL), dried under reduced pressure to give crude 3,5-dibromo-l-tetrahydropyran-2-yl-l,2,4-triazole (155 g, 75%) as a white solid. NMR (400 MHz, CDCl3) delta 5.49 – 5.46 (m, 1H), 4.12 – 3.99 (m, 1H), 3.72 – 3.61 (m, 1H), 2.38 – 2.26 (m, 1H), 2.18 – 2.07 (m, 1H), 1.98 – 1.90 (m, 1H), 1.78 – 1.60 (m, 3H).

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 3,5-Dibromo-1H-1,2,4-triazole, in my other articles.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 4320-91-6, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 4320-91-6, name is 2H-1,2,3-Triazole-2-acetic acid, molecular formula is C4H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Oxalyl chloride (0. 95 mL, 11 mmol) was added dropwise to a suspension OF 2- (1-1, 2, 3-triazolyl)) acetic acid (Step B, 1.27 g, 10 mmol) in 10 ML CH2C12 containing 0.05 ML DMF. Vigorous effervescence was observed. This mixture was stirred at room temperature for 4 h and cooled TO-78C. A solution OF N. O- dimethylhydroxylamine hydrochloride (1.2 g, 13 mmol) and diisopropylethyl amine (6.0 mL, 35 mmol) in 10 ML CH2CL2 was added slowly over 3 min. The mixture was then allowed to warm to room temperature and stirred overnight. The reaction mixture was then diluted with ether until no additional precipitate appeared. The solid was filtered and washed with ether. The filtrate was concentrated and the residue was purified on silica gel using EtOAc as solvent to provide the title compound as amorphous solid. 1H NMR (400 MHz, CDC13) : S 3.252 (s, 3H0, 3.812 (s, 3H), 5.379 (s, 2H), 7.753 & 7.761 (s’s, 2H).

The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about 2H-1,2,3-Triazole-2-acetic acid is helpful to your research.

Reference:
Patent; MERCK & CO., INC.; WO2005/27837; (2005); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7411-23-6, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Intermediate 2 3,5-Dibromo-l-(2-methylallyl)-lH-l,2,4-triazole 3,5-Dibromo-lH-l,2,4-triazole (1.5 g, 6.61 mmol) in DMF (13 mL) was treated with sodium tert- pentoxide (0.728 g, 6.61 mmol) and the mixture was stirred for 10 min at rt under nitrogen atmosphere. 3-Bromo-2-methylprop-l-ene (0.667 mL, 6.61 mmol) was added and the mixture was stirred at 40C for 2 hours. The mixture was poured onto water and extracted with diisopropylether (2x). The organic phase was washed with water (2x), brine and dried (sodium sulfate). The solvents were evaporated to give the title compound as a liquid (1.70 g, 91%). GCMS (CI) m/z 281 [M+]. XH NMR (400 MHz, CDCI3) delta ppm 1.74 (d, 3 H) 4.69 (s, 2 H) 4.81 – 4.86 (m, 1 H) 5.05 (dd, 1 H).

The potential utility of systematic synthetic strategy will be applicable to efficient generations of chemical libraries of compounds to find ‘hit’ molecules.Read on for other articles about 3,5-Dibromo-1H-1,2,4-triazole, hurry up and to see.

Reference:
Patent; ACTURUM LIFE SCIENCE AB; BESIDSKI, Yevgeni; YNGVE, Ulrika; PAULSEN, Kim; LINDE, Christian; NORDVALL, Gunnar; MACSARI, Istvan; MALMBORG, Jonas; WO2014/195321; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H4BrN3

Intermediate 602: 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole Compound 601 (0.6 g, 3.69 mmol) was dissolved in 15 ml of 1,4-dioxane, added with 1.125 g (4.43 mmol) of bis(pinacolato)diboron, 1.086 g (11.07 mmol) of potassium acetate, and 0.3 g (0.37 mmol) of [1,1-bis(di-phenylphosphino)ferrocene]palladium chloride dichloromethane complex under the protection of nitrogen, heated to 95 C, reacted for 5 h, and then cooled to room temperature. 50 mL of water was added and stirred for 30 min, and filtered to afford 0.35 g of solid. Yield: 45.39%.

The catalyzed pathway has a lower Ea, but the net change in energy that results from the reaction is not affected by the presence of a catalyst. In my other articles, you can also check out more blogs about 13273-53-5

Reference:
Patent; Beijing Forelandpharma Co. Ltd.; ZHANG, Xingmin; JI, Qi; WANG, Lei; GAO, Congmin; WANG, Ensi; DU, Zhenjian; GONG, Longlong; CHEN, Bo; (137 pag.)EP3072893; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7170-01-6, New Advances in Chemical Research in 2021.In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a solution of 4-fluorobenzaldehyde (3.63 g) and 3-methyl-lH-l,2,4-triazole (2.92 g; prepared according to US 2006/293304) in dry DMF (35 mL) was added K2C03 (24.25 g) at rt. The reaction mixture was stirred at 120C overnight, then cooled to rt and diluted with EA and water. The aq. layer was extracted with EA (2x) and the combined org. layers were washed with water and brine, dried over MgS04, filtered and concentrated under reduced pressure. The title compound was obtained, after purification by CC (Hept/EA 80:20 to 50:50), as a yellow solid (36% yield).1H NMR (CDCls) delta: 10.06 (s, 1H); 8.58 (s, 1H); 8.04 (d, J = 8.0 Hz, 2H); 7.88 (d, J = 8.0 Hz, 2H); 2.53 (s, 3H).

Future efforts will undeniably focus on the diversification of the new catalytic transformations. These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. Keep reading other articles of 7170-01-6.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Methyl-1H-1,2,4-triazole

To a suspension of 60% sodium hydride in oil (0.3 g) in dimethylformamide (50 ml) was added dropwise 3-methyl-1,2,4-triazole (0.45 g). After hydrogen gas evolution ceased, 4-fluoro-2-trifluoromethyl-phenyl-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-yl)-methanone (1.76 g) was added and the reaction mixture was heated in a sand bath at 110 C. for 18 hours. The mixture was poured onto ice, diluted with brine, and extracted with dichloromethane. The combined extracts were dried over anhydrous sodium sulfate and filtered through a short column of anhydrous sodium magnesium silicate. The solution was concentrated in vacuo and the residue was triturated with diethyl ether to give 0.81 g of the title compound as colorless crystals, m.p. 148-150 C., MS m/z: 438.2 (M+H)+, 875.8 (2M+H)+.

If you are hungry for even more, make sure to check my other article about 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7411-23-6, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) and p-quinonemethide precursor 7 (2.9 mmol) were refluxed for 4 h in DMF (10mL). Products were isolated analogously to compound 4a.

Future efforts will undeniably focus on the diversification of the new catalytic transformations. These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. Keep reading other articles of 7411-23-6.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics