Triazoles

Synthetic Route of 288-36-8, 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. 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To 2H-1,2,3-triazole (2.0 g, 29 mmol) in DMF (145 ml) was added NaH (1.16 g, 29 mmol, 60% inmineral oil) at RT and the mixture was stirred for 1h. After cooling to 0C, 2-chloro-1-fluoro-4-nitrobenzene (4.6 g, 26.1 mmol) was added and the reaction mixture was stirred at 0C for 1.5h,then at RT for 1.5h. The mixture was quenched with water and extracted with ethyl acetate. Theorganic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated.The crude product was purified by chromatography on silica gel (heptane/AcOEt: 90/10 to 50/50)to afford 2-(2-chloro-4-nitrophenyl)-2H-1,2,3-triazole.

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Reference:
Article; Schlapbach, Achim; Revesz, Laszlo; Pissot Soldermann, Carole; Zoller, Thomas; Regnier, Catherine H.; Bornancin, Frederic; Radimerski, Thomas; Blank, Jutta; Schuffenhauer, Ansgar; Renatus, Martin; Erbel, Paulus; Melkko, Samu; Heng, Richard; Simic, Oliver; Endres, Ralf; Wartmann, Markus; Quancard, Jean; Bioorganic and Medicinal Chemistry Letters; vol. 28; 12; (2018); p. 2153 – 2158;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

General procedure: A solution of 21% (w/v) sodium ethoxide (9.13 mL, 24.46 mmol) in ethanol was added to a solution of 3-methyl-1H-1,2,4-triazol-5-amine (2 g, 20.39 mmol) and diethylmalonate (3.42 mL, 22.42 mmol) in Ethanol (10 mL) in a 100 mL round bottomed flask. The resulting mixture was stirred at 75 C overnight. The reaction mixture was cooled and the resulting precipitate was filtered and rinsed with EtOH. The solid was air dried to yield an off white solid (2.84g, 84%). 1H NMR (400 MHz, DEUTERIUM OXIDE) ppm 2.21 (s, 3 H) 4.87 (s, 1 H); LC/MS: MS(ES+) m/e 167 (MH+).

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 4923-01-7

Reference:
Article; Sanchez, Robert M.; Erhard, Karl; Hardwicke, Mary Ann; Lin, Hong; McSurdy-Freed, Jeanelle; Plant, Ramona; Raha, Kaushik; Rominger, Cynthia M.; Schaber, Michael D.; Spengler, Michael D.; Moore, Michael L.; Yu, Hongyi; Luengo, Juan I.; Tedesco, Rosanna; Rivero, Ralph A.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 9; (2012); p. 3198 – 3202;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 13273-53-5, 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. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, 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 the crude (S)-4-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide (30 mg, 0.059 mmol) in residual dioxane was added 4-bromo-1-methyl-1H-1,2,3-triazole (14.24 mg, 0.088 mmol), PdCl2(dppf) (42.9 mg, 0.059 mmol), DME (195 mul) and 2 M Na2CO3 (130 mul) at room temperature. The reaction mixture was stirred for 5 h. After water and EtOAc were added, the organic layer was extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered off, and concentrated in vacuo. The crude product was purified by prep HPLC. The pure fractions were lyophilized yielding (S)-4-(2-amino-5-(1-methyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide as a TFA salt (25% over 2 steps). LCMS (m/z): 467.3 (MH+), 0.61 min; 1H NMR (400 MHz, CD3OD) delta ppm 8.64 (m, 1H), 8.31 (m, 1H), 8.25 (m, 2H), 8.2 (m, 1H), 7.82 (m, 1H), 7.4 (m, 3H), 7.28 (m, 2H), 7.22 (m, 1H), 5.11 (m, 1H), 4.07 (s, 3H), 3.78 (m, 2H).

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Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1H-1,2,4-Triazol-5-amine

General procedure: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

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 61-82-5

Reference:
Article; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 135242-93-2, 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. 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, molecular formula is C4H7N3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a mixture of (l-methyl-l/-/-l,2,4-triazol-3-yl)methanol (400 mg, 3.54 mmol) and iodobenzene diacetate (1.25 g, 3.89 mmol) in dichloromethane (10 mL) was added TEMPO ((2, 2,6,6- tetramethylpiperidin-l-yl)oxyl) (56 mg, 354 pmol). The mixture was stirred at 15-20C for 2h. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ethenethyl acetate = 1:2) to give l-methyl-l/-/-l,2,4-triazole-3-carbaldehyde (300 mg, 2.70 mmol, 76% yield). XH NMR (chloroform-d 400 MHz) d 10.01 (s, 1H), 8.19 (s, 1H), 4.06 (s, 3H).

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Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (278 pag.)WO2019/115567; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Bromo-1H-1,2,4-triazole

Sodium hydride (1.2eq) was added to a solution of 3-bromo-lH-[l,2,4]triazole (leq) in dry DMF (2.3ml/mmol) at 00C and under an atmosphere of nitrogen The solution was stirred at 00C for 20min, then, SEM-Cl (1.2eq) was added. The mixture was stirred at room temperature overnight and diluted with H2O and ethyl acetate. The organic layers was washed with H2O then brine, dried on anhydrous Na2SO4, filtered and concentrated in vacuum to give the titled compound. Crude compound 3- bromo-l-(2-trimethylsilanyl-ethoxymethyl)-lH-[l,2,4]triazole was engaged in step 2 without purification. IH-NMR (CDCl3): delta (ppm) 0.00 (t, 9H); 0.92 (t, 2H); 3.64 (t, 2H); 5.44 (s, 2H); 8.13 (s, IH)

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Reference:
Patent; VIVALIS; BERECIBAR, Amaya; GUEDAT, Philippe; MOHAMED-ARAB, Celine; WO2011/4017; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 27996-86-7, New Advances in Chemical Research in 2021.Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, molecular formula is C9H7N3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Stage 79.4: (4-[1,2,4] Triazol-1-yl-benzylamino)-acetic acid ethyl esterTo a solution of 3.5 g (20 mmol) of 4-[1,2,4] triazol-1-yl-benzaldehyde and 4.19 g (30 mmol) of glycine ethyl ester hydrochloride in 100 ml of CH2Cl2, 4.18 ml (30 mmol) of triethyl amine and excess of MgSO4 (14 g) are successively added at r.t. After being stirred for 18 h at r.t., the reaction mixture is filtered through celite and concentrated under reduced pressure. The residue is diluted with AcOEt and filtered again. The filtrate is concentrated under reduced pressure to give the crude imine. To a solution of the crude imine in 12 ml of MeOH, 0.756 mg (20 mmol) of NaBH4 is added at -10 C. After being stirred for 1 h, the reaction is quenched with sat. NH4Cl and the reaction mixture is extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: n-Hexane: AcOEt=1:10) to give the title compound. 1H-NMR (400 MHz, CDCl3): 1.29 (t, 3H, J=7.04 Hz), 1.90 (brs, 1H), 3.43 (s, 2H), 3.88 (s, 2H), 4.21 (q, 2H, J=7.04 Hz), 7.49 (d, 2H, J=8.56 Hz), 7.64 (d, 2H, J=8.56 Hz), 8.10 (s, 1H), 8.55 (s, 1H).

I am very proud of our efforts over the past few months and hope to 4-[1,2,4]Triazol-1-yl-benzaldehyde help many people in the next few years.

Reference:
Patent; Novartis AG; US7138432; (2006); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C3H3N3O2

[0683] Compound 3b (7.0 mg, 16 f.tmol) was combinedwithDMF (0.5 mL), lH-1,2,3-triazole-5-carboxylic acid (2.0mg, 18 f.tmol), HATU (6.8 mg, 18 flillOl) and DIPEA (8.5 f.LL,49 f.tmol). The mixture was stirred for 30 minutes after whichtime LCMS showed the desired product formation. The solutionwas concentrated in vacuo to yield Compound 4b whichwas used directly in the next step.

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Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world.4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

Step 1 Preparation of 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester A solution of 1H-[1,2,4]triazole-3-carboxylic acid methyl ester (3.0 g, 0.23 mol) in N,N-dimethylformamide (76 mL) at 25° C. was treated with triphenylmethylchloride (7.2 g, 0.23 mol) and triethylamine (6.41 mL, 0.23 mol). The reaction mixture was stirred at 25° C. for 4 days and then diluted with ethyl acetate. The mixture was then washed with a dilute aqueous hydrochloric acid solution. At this time, methanol was added to the organic layer. A precipitate formed and was removed by filtration. The organics were further washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was triturated with diethyl ether. The solid was collected by filtration and washed again with diethyl ether to afford 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester as a white solid (2.45 g, 84percent) which was used without further purification: LR-FAB for C23H19N3O2 (M+) at m/z=369.

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Reference:
Patent; Dunten, Peter W.; Foley, Louise H.; Huby, Nicholas J.S.; Pietranico-Cole, Sherrie L.; Yun, Weiya; US2004/14766; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 61-82-5, 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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

General procedure: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

We very much hope you enjoy reading the articles and that you will join us to present your own research about 61-82-5, Happy reading!

Reference:
Article; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics