Day: July 6, 2021

New discoveries in chemical research and development 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. 288-36-8, name is 1H-1,2,3-Triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 288-36-8

DMF (1.5 ml) was added to a mixture of methyl S-iodo-beta-methyl-l-pyridinecarboxylate D36 (100 mg), lH-l,2,3-triazole (49.9 mg, 0.722 mmol), (lR,2R)-N,N’-dimethyl-l,2- cyclohexanediamine (10.27 mg, 0.072 mmol), CuI (3.44 mg, 0.018 mmol) and Cs2CO3 carbonate (235 mg, 0.722 mmol) in a microwave vial. The mixture was degassed via three vacuum/nitrogen cycles then irradiated in a single mode microwave reactor to 120 0C for 20 minutes. The mixture was irradiated in a single mode microwave reactor to 120 0C for a further 40 minutes. The reaction mixture was cooled and filtered washing the solids with EtOAc. The solids were dissolved in pH = 3 buffer solution (5 ml); UPLC check of this aqueous solution showed it contained a considerable quantity of 6-methyl-3-(2H- l,2,3-triazol-2-yl)-2-pyridinecarboxylic acid. The aqueous phase was extracted repeatedly with DCM; the combined DCM extracts were diluted with MeOH (50 ml) and treated with TMS-diazomethane. The volatiles were evaporated to give a yellow residue that was purified by flash chromatography on silica gel (Biotage, SNAP 1O g column, 10 %-50 % EtOAc/Cy) to give the title compound D39 (38 mg) as a white solid. UPLC (BasicQC_POS_50-800): rt = 0.57 minutes, peak observed: 219 (M+l). C10H10N4O2 requires 218. 1H NMR (400 MHz, CDCl3) delta ppm 8.20 (d, 1 H), 7.87 (s, 2 H), 7.44 (d, 1 H), 3.94 (s, 3 H), 2.71 (s, 3 H)

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Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; CASTIGLIONI, Emiliano; DI FABIO, Romano; PAVONE, Francesca; WO2010/63662; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 138479-53-5, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 138479-53-5, name is 2-[1,2,4]Triazol-1-yl-benzaldehyde, 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.

To a round bottom flask is added 4-(2-amino-4-methoxy-pyrimidin-5-yl)-N^-ieri-butyl- benzene- 1,2-diamine (118 mg, 0.411 mmol) in DMF (4 mL) and water (1 mL), followed by the addition of 2-1,2,4-triazol-l-yl-benzaldehyde (78 mg, 0.45 mmol) and oxone (51 mg, 0.443 mmol). The reaction mixture is stirred at room temperature for 4 hours. Sat. sodium thiosulfate (10 mL) is added. The reaction mixture is diluted with EtOAc. The organic layer is separated, washed with water then brine, dried with Na2S04, filtered and concentrated. The residue is loaded into a silica gel column. The column is eluted with 0- 4% 7M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford the title compound (67 mg, 37 %) as a light brown solid. LCMS (ESMS): m/z 441.73 (M++l)

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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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 6523-49-5

A cooled (0 0C) solution of 6-(cyclopropylmethyl(propyl)amino)pyrimidine-4- carboxylic acid (Intermediate 21 , 112 mg; 0.45 mmol) in DCM was treated with diisopropylethylamine (78.4 ml 0.52 mmol) and methyl chloroformate (36.2 ml 0.47 mmol). After stirring at 0 0C for 15 minutes, 4-(1 H-1 ,2,4- triazol-1-yl)aniline (Maybridge, 108 mg; 0.67 mmol) was added and the mixture stirred for 72 hours. The solvent was evaporated and the compound purified by preparative HPLC to give the title compound as a white solid.1H NMR (400MHz, CDCI3) delta 10.13 (1 H, s), 8.56 (2H, d, J = 13.9 Hz), 8.11 (1 H, s), 7.93 (2H, d, J = 8.6 Hz), 7.70 (2H, d, J = 8.6 Hz), 7.36 (1 H, s), 3.53 (4H, s), 1.75-1.65 (2H, m), 1.10 (1 H, s), 0.97 (3H, t, J = 7.4 Hz), 0.58 (2H, d, J = 7.7 Hz), 0.35-0.30 (2H, m). MS (ESI+) 378. HPLC (Condition C) Rt 3.70 min (HPLC purity 99.8%).

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Reference:
Patent; LABORATOIRES SERONO SA; WO2009/19167; (2009); 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. 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C2HBr2N3

Step 2. tert-butyl 4-(4,5-dibromo-2H-l,2,3-triazol-2-yl)piperidine-l-carboxylate and tert-butyl 4-(4,5-dibromo-lH-l,2,3-triazol-l-yl)piperidine-l-carboxylate [0261] A mixture of 4,5-dibromo-2H-l,2,3-triazole (2.27 g, 10.08 mmol), tert-butyl 4- (methylsulfonyloxy)piperidine-l -carboxylate (2.79 g, 10.00 mmol), and cesium carbonate (9.75 g, 29.91 mmol) in N,N-dimethylformamide (50 mL) stirred overnight at 100 °C. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford a mixture of tert-butyl 4-(4,5-dibromo-2H- 1 ,2,3- triazol-2-yl)piperidine- 1 -carboxylate and tert-butyl 4-(4,5-dibromo- 1 H- 1 ,2,3-triazol- 1 -yl)piperidine- 1-carboxylate (4.00 g, 97percent) as a yellow oil. MS (ESI, pos. ion) m/z 411 , 409, 413 [M+H]+. Step 3. tert-butyl 4-(4-bromo-2H-l,2,3-triazol-2-yl)piperidine-l-carboxylate (Intermediate 19) and tert-butyl 4-(4-bromo-lH-l,2,3-triazol-l-yl)piperidine-l-carboxylate (Intermediate 20) [0262] n-Butyllithium (2.5 M in hexanes, 2.92 mL, 7.30 mmol) was added dropwise to a -78 °C solution containing a mixture of tert-butyl 4-(4,5-dibromo-2H- 1,2, 3-triazol-2-yl)piperi dine- 1- carboxylate and tert-butyl 4-(4,5-dibromo-lH-l,2,3-triazol-l-yl)piperidine-l -carboxylate (3.00 g, 7.35 mmol) in tetrahydrofuran (20 mL). The resulting solution stirred for 1 hour at -78 °C, and then the reaction mixture was poured into saturated aqueous ammonium chloride solution (20 mL). The aqueous phase was separated and extracted with ethyl acetate (3 x 20 mL), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 2: 1, ethyl acetate/petroleum ether) to afford tert-butyl 4-(4-bromo-2H-l,2,3-triazol-2-yl)piperidine-l- carboxylate (0. 800 g, 33percent) as a colorless oil. MS (ESI, pos. ion) m/z 331, 333[M+H]+. [0263] tert-Butyl 4-(4-bromo-lH-l ,2,3-triazol-l-yl)piperidine-l-carboxylate (0.500g, 20percent) was also obtained as a colorless oil. MS (ESI, pos. ion) m/z 331, 333 [M+H]+.

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 4,5-Dibromo-2H-1,2,3-triazole, in my other articles.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 74205-82-6, New Advances in Chemical Research 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. 74205-82-6, name is (1H-1,2,4-Triazol-1-yl)methanol, molecular formula is C3H5N3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

The indoline (1) (10.0 (^, 0.08311101) was added to a 11 round bottom flask, Glacial acetic acid 1001111, stirring at room temperature 0.5h, adding triazole methyl alcohol (16.61 g, 0.167 mol), and the reaction was stirred at 80 C for 3 h. TLC indicated that the reaction was complete and stopped The reaction was cooled to room temperature, 40% aqueous sodium hydroxide (100 ml) and 100 ml of methanol were added under ice-cooling, refluxed for 0.5 h at 70 C, Dichloromethane (75 mL x 3), saturated brine (150 ml x 2), dried over anhydrous sodium sulfate and concentrated to give Yellow oil 7.74 g (2), yield 46.6%

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 74205-82-6.

Reference:
Patent; Sichuan University; Wu, Yong; Guan, mei; Zhao, yinbo; Hai, Li; He, Yi; Li, Xiao Cen; (9 pag.)CN103664901; (2016); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1001401-62-2, 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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, molecular formula is C9H7N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Asolution of 2- (2H-1, 2, 3-triazol-2-yl) benzoic acid (6.8 g, 36 mmol) in SOCl2(30 mL) was stirred at RT for 30 mins. The solvent was removed in vacuo. To asolution of the product from Step 2 (6.0 g, 36 mmol) in dry toluene (50 mL) wasadded 1 N aqueous NaOH (73 mL, 0.073 mol) at 0 and asolution of the above residue in toluene (30 mL) dropwise . The resultingmixture was stirred at RT overnight and extracted with EtOAc (100 mL x 3) . Thecombined organic layers were washed with brine, dried over Na2SO4,filtered, and concentrated in vacuo to give the title compound as an oil, whichwas used without further purification. LRMS m/z (M+H) 508.1 found, 508.2required

In the meantime we’ve collected together some recent articles in this area about 1001401-62-2 to whet your appetite. Happy reading!

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; LUO, Yunfu; (47 pag.)WO2016/65587; (2016); A1;,
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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3,5-Diamino-1,2,4-triazole

To a solution of compound 8 (5.71 mmol) in 10 mL of glacial acetic acid, was added diaminotriazole 10 (8.56 mmol) and heated to reflux for 4 h. The reaction mixture was cooled, and the solvent evaporated in vacuo to produce a pale-yellow solid. The solid was washed with water and recrystallized from ethanol to furnish the title compound as white crystals. (adapted from 1). Yield 72percent (0.87 g). 1H NMR (600 MHz, DMSO-d6) delta 8.53 (d, J = 4.8 Hz, 1H), 8.21 ? 8.10 (m, 2H), 7.63 ? 7.57 (m, 3H), 7.25 (d, J = 4.8 Hz, 1H), 6.45 (s, 2H). HRMS-ESI (+) m/z calculated for C11H10N5, 212.0936 [M+H]+; found: 212.0939.

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-Diamino-1,2,4-triazole, in my other articles.

Reference:
Article; Ribeiro, Carlos J.A.; Kankanala, Jayakanth; Xie, Jiashu; Williams, Jessica; Aihara, Hideki; Wang, Zhengqiang; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 257 – 261;,
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. 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C10H9N3O2

General procedure: TEA (1.20 mL, 8.63 mmol) was added to a solution of N-ethyl-2[3-(5-fluoro-pyridin-2-yl)-1H-pyrazol-l-yl] ethanamine dihydrochloride(0.50 g, 1.63 mmol) in CHC13 (5 mL) at room temperature.5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (0.36 g, 1.79 mmol)and propylphosphonic acid anhydride (cyclic trimer) (50% solutionin DMF [approximately 1.6 mol/L], 1.32 mL, 2.12 mmol) wereadded to the reaction solution under cooling in ice water. Theresultant mixture was stirred at 50 C for 5 h. After standing untilcooled to room temperature, water was added thereto, followedby extraction with CHCl3. The organic layer was washed with brine.Then, the organic layer was dried over MgSO4 and the desiccantwas filtered off. Then, the solvent was distilled off under reducedpressure. The obtained residue was purified by column chromatography(20-80% EtOAc in hexanes) and washed with Et2O to yieldthe title compound 4a as a colorless powder (0.51 g, 75%).

If you are hungry for even more, make sure to check my other article about 956317-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Suzuki, Ryo; Nozawa, Dai; Futamura, Aya; Nishikawa-Shimono, Rie; Abe, Masahito; Hattori, Nobutaka; Ohta, Hiroshi; Araki, Yuko; Kambe, Daiji; Ohmichi, Mari; Tokura, Seiken; Aoki, Takeshi; Ohtake, Norikazu; Kawamoto, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1260 – 1275;,
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. 1157938-97-0, name is 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 1157938-97-0

a) Preparation of a Stock-solution of lithium-diisopropylamide (LDA) in tetrahydrofuran (THF): Diisopropylamine (716 mg, 7,1 mmol, 1.05 eq) was dissolved in anhydrous THF (21.3 mL) and the resulting solution was cooled to -78 C under a nitrogen atmosphere. Subsequently, -BuLi (2,7 M solution in w-heptane, 2.5 mL, 6.7 mmol, 1,0 eq) was added in a drop wise fashion over 15 minutes and the reaction mixture was stirred at -78 C for an additional 15 minutes. Then the solution was warmed to 0 C and stirred for 30 minutes after which the stock solution was cooled to -78 C again, b) Coupling reaction: The thus obtained LDA-solution (3,66 mL, 0.98 mmol, 1.1 eq) was transferred to a Schlenk vessel and ethylpropionate (100 mg, 0.98 mmol, 1.1 eq.) was added in a drop wise fashion at -78 C under a nitrogen atmosphere. The resulting mixture was stirred at -78 C for 30 minutes and then l-(2,5-difluorophenyl)-2-(lH-l,2,4-triazol-l-yl)ethanone (200 mg, 0.90 mmol, 1.0 eq.) in THF (3.66 mL) was added in a drop wise fashion over 15 minutes. The reaction mixture was stirred for 2 hours at -78 C and then quenched with acetic acid and warmed to room temperature. The mixture was diluted with aqueous saturated NH4C1 and ethylacetate. The aqueous layer was extracted with ethylacetate (2x) and the combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated in vacuo to give a yellow oil containing the racemic ester I with a diastereomeric excess of 29% in favour of the desired RR/SS diastereomer. Further purification by column chromatography (-heptane/EtOAc/MeOH 60/40/5 v/v/v) provided the RR/SS diastereomer (light yellow solid) as well as the RS/SR diastereomer (off-white solid) in a combined overall yield of 179 mg (0.55 mmol, 61%).

If you are hungry for even more, make sure to check my other article about 1157938-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASILEA PHARMACEUTICA AG; VAN SUMMEREN, Ruben; VAESSEN, Harrie; MINK, Daniel; WASER, Mario; WO2014/23623; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 27808-16-8, 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. 27808-16-8, name is 4-Methyl-1H-1,2,3-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.

A solution of 4-methyl-iH-i,2,3-triazole (500 mg,6.02 mmol), 2,3-dichloro-5-nitropyridine (1277.42 mg, 6.62 mmol), K2C03 (2491.22 mg, 18.05 mmol) in CH3CN (5 mE) was stirred at it for 12 h. The mixture was concentrated under reduced pressure, the crude product was purified by colunm chromatography over silica gel (petroleum ether ethyl acetate from 20:1 to 1:1). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford i25a (1.1 g, 76.3%) as a yellow solid. ECMS (ESI) mlz M+i: 239.7. Zn (1491.96 mg, 22.95 mmol) was added to a solution of mixture of 3-chloro-2-(4-methyl-2H-i,2,3-tri- azol-2-yl)-5-nitropyridine and 3-chloro-2-(4-methyl-i H-i, 2,3-triazol-i-yl)-5-nitropyridine, i25a (1.1 g, 2.30 mmol) in aqNH4C1 (30 mE) and H20 (30 mE). The mixture was stirred at it for 16 h. To the suspension was added aq NaHCO3 to adjust to pH 9-10, and the mixture was filtered through a pad of diatomaceous earth. The filter cake was washed with CH2C12 (100 mEx3). The combined filtrates were washed with brine (200 mE), dried over MgSO4 and concentrated under reduced pressure to afford mixture of 5-chloro-6-(4-methyl-2H- 1 ,2,3-triazol-2-yl)pyridin-3-amine and 5-chloro-6-(4-methyl-i H-i ,2,3-triazol- 1 -yl)pyriF din-3-amine, 125b (1 g) as a brown solid, used directly for the next step. LCMS (ESI) mlz M+H: 209.7

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 27808-16-8.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics