Category: 27808-16-8

Electric Literature of 27808-16-8, The chemical industry reduces the impact on the environment during synthesis 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

Example 74 N-((1S)-2-hydroxy-2-methyl-1-(4-(trifluoromethoxy)phenyl)propyl)-5-(4-methyl-1H-1,2,3-triazol-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide A solution of (S)-5-chloro-N-(2-hydroxy-2-methyl-1-(4-(trifluoromethoxy)phenyl)propyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (200 mg), 4-methyl-1H-1,2,3-triazole (46.5 mg) and potassium carbonate (97 mg) in N,N-dimethylformamide (2 mL) was stirred at 80 C. for 2 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was fractionated by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA-containing system)). The obtained fraction with a shorter retention time was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was crystallized from hexane/ethyl acetate to give the title compound (37.5 mg).MS (API+): [M+H]+476.2.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Methyl-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (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. 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Formula: C3H5N3

General procedure: Methyl 2,6-difluoro-4-{[(4-iodophenyl)sulfonyl]amino}benzoate (4.5 g, 9.9 mmol) was dissolved in N-methylpyrrolidone (90 ml), and 1,2,3-triazole (1.50 g, 21.7 mmol), copper(I) iodide (1.20 g, 6.30 mmol), potassium phosphate (6.0 g, 28 mmol), and trans-N,N?-dimethylcyclohexane-1,2-diamine (1.50 g, 10.5 mmol) were added thereto, followed by stirring at 145 C. for 12 hours in the presence of nitrogen gas. After cooling to room temperature, the reaction solution was diluted with water, followed by extraction with ethyl acetate (150 ml¡Á5). The extraction liquids were combined, washed with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. Then, the solvent was removed. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=2:1 to 1:1) to obtain methyl 2,6-difluoro-4-({[4-(1H-1,2,3-triazol-1-yl)phenyl]sulfonyl}amino)benzoate (M-17) (650 mg, 17%) and methyl 2,6-difluoro-4-({[4-(2H-1,2,3-triazol-2-yl)phenyl]sulfonyl}amino)benzoate (M-18) (800 mg, 20%). The title compound (252 mg, 4%) was obtained as a white solid by subjecting methyl 2,5-difluoro-4-[(4-iodophenyl)sulfonylamino]benzoate (7.00 g, 15.5 mmol) and 4-methyl-1H-triazole (2.50 g, 30.1 mmol) to the same methods as in Examples 15 to 18. [1338] 1H NMR (400 MHz, DMSO-d6): delta 11.18 (s, 1H), 8.67 (s, 1H), 8.15 (m, 2H), 8.06 (m, 2H), 7.68-7.63 (m, 1H), 7.34-7.29 (m, 1H), 3.80 (s, 3H), 2.33 (s, 3H)

The synthetic route of 27808-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, 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 27808-16-8, Computed Properties of C3H5N3

DMF (1.5 ml) was added to a mixture of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D44 (200 mg), 4-methyl-1H-1,2,3-triazole D77 (120 mg), (1R,2R)-N,N’-dimethyl-1,2-cyclohexanediamine (20.54 mg, 0.144 mmol), copper(I) trifluoromethanesulfonate benzene complex (18.17 mg, 0.036 mmol) and cesium carbonate (470 mg, 1.444 mmol) in a screw-topped vial. The mixture was degassed via 3 vacuum/nitrogen cycles and heated with shaking to 120 C. for 5 hours. The reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in water/MeOH (1:1, 3 ml) and acidified to pH=2 by addition of 2 M HCl solution. The resulting mixture was evaporated to dryness under reduced pressure then the residue was triturated with DCM/MeOH (3:1, 5 ml). The mixture was filtered washing with more DCM/MeOH (3:1, 5 ml). The filtrate was treated with TMS-diazomethane solution (2 M in hexanes, 4 ml, 8 mmol) to re-esterify the acid. The reaction mixture was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (Biotage Snap 25 g column, EtOAc/Cy from 20/80 to 50/50) to give the title compound D78 (121 mg) as a colourless solid. UPLC (Acid QC_POS-50-800): rt=0.59 minutes, peak observed: 233 (M+1). C11H12N4O2 requires 232. 1H NMR (400 MHz, CDCl3) delta ppm 8.15 (d, 1H), 7.59 (s, 1H), 7.37 (d, 1H), 3.92 (s, 3H), 2.66 (s, 3H), 2.40 (s, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 27808-16-8

N-Bromosuccinimide (5.89 g, 33.i mmol) was added to a solution of 4-methyl-iH-i,2,3-triazole (2.50 g, 30.i mmol) in chloroform (30 mL), and the reaction mixture was stirred for i6 hours at room temperature (i5 C). It was then diluted with dichloromethane (iOO mL), washed with water (2 x iOO mL), dried over sodium sulfate, filtered, and concentrated in vacuo to provide the product as a white solid (4.9 g), which was used directly in the next step.

According to the analysis of related databases, 27808-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; CHAPPIE, Thomas Allen; CHEN, Jinshan Michael; COE, Jotham Wadsworth; COFFMAN, Karen Jean; GALATSIS, Paul; GARNSEY, Michelle Renee; HELAL, Christopher John; HENDERSON, Jaclyn Louise; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G.; MARTINEZ-ALSINA, Luis Angel; PETTERSSON, Martin Youngjin; REESE, Matthew Richard; ROSE, Colin Richard; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; WARMUS, Joseph Scott; ZHANG, Yuan; (193 pag.)WO2018/163066; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 27808-16-8, 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. 27808-16-8 name is 4-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.

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

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

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

Electric Literature of 27808-16-8,Some common heterocyclic compound, 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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.

3-bromo-6-methylpyridine-2-carboxylic acid (408 mg, 1 .89 mmol) was dissolved in a mixture of 1 ,4-Dioxane (2ml_)Water (0.200ml_), then 4-Methyl-1 H-1 ,2,3-triazole (236 mg, 2.84 mmol), cesium carbonate (1 .24 g, 3.78 mmol), Cul (18 mg, 0.09 mmol) and (1 R,2R)-N 1 , N2-dimethylcyclohexane-1 ,2-diamine (54 mg, 0.38 mmol) were added. The mixture was stirred at 120 C for 2 hrs. Reaction mixture was cooled to RT and then water and MTBE were added. After vigorously stirring, the layers were separated and the aqueous one was acidified to pH 2 with HCI 6N. The acidic solution was concentrated and purified by RP on C18 column [eluting H20 (0.1 % HCOOH)/CH3CN from 100:0 to 60:40] affording 6-methyl-3-(4-methyl-2H-1 ,2,3-triazol-2-yl)pyridine-2-carboxylic acid (p95, 274 mg, y= 66% yield) and 6-methyl-3-(4-methyl-1 H-1 ,2,3-triazol-1 -yl)pyridine-2- carboxylic acid (p96, 40 mg, y=10%) as a white solids. P95 MS (/77/z): 219.2 [MH]+ 1 H NMR (MeOD-d4) delta 8.17 (d, 1 H), 7.72 (s, 1 H), 7.54 (br. s., 1 H), 2.62 (br. s., 3 H), 2.38 (s, 3 H) P96 MS (mlz): 219.2 [MH]+ 1 H NMR (MeOD-d4) delta 8.05 (s, 1 H), 7.94 (d, 1 H), 7.62 (d, 1 H), 2.67 (s, 3 H), 2.40 (s, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-1H-1,2,3-triazole, its application will become more common.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 27808-16-8,Some common heterocyclic compound, 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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.

The 5-chloro-6-methyl-pyrazolo [1,5-a] pyrimidine-3-carboxylic acid butyl 3rd (607 mg) for N, N- dimethyl formamide (39.8 ml) is added a solution of 4-methyl -1H-1, 2, 3-triazole (208 mg) and potassium carbonate (378 mg). The reaction mixture is stirred at room temperature for 2 hours, to be added, and the mixture is extracted with ethyl acetate. Extract water and saturated salt water cleaning, drying with anhydrous sodium sulfate, and the evaporation of the solvent under reduced pressure. Aid hemostasis by silica gel column chromatography purification (hexane/ethyl acetate), in order to produce the title compound (167 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-1H-1,2,3-triazole, its application will become more common.

Reference:
Patent; TAKED A PHARMACEUTICAL COMPANY LIMITED; KAWASAKI, MASANORI; MIKAMI, SATOSHI; NAKAMURA, SHINJI; NEGORO, NOBUYUKI; IKEDA, SHUHEI; ASHIZAWA, TOMOKO; MARUI, SHOGO; TANIGUCHI, TAKAHIKO; (135 pag.)TW2016/520; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, 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 27808-16-8, SDS of cas: 27808-16-8

A mixture of 33(430 mg, 1.00 mmol), 4-methyl-1H-1,2,3-triazole (100 mg,1.20 mmol) and K2CO3 (208 mg, 1.50 mmol) in DMF (4 mL)was stirred at 80C for 2 h. The mixture was quenched withwater at r.t. and extracted with EtOAc. The organic layer wasseparated, washed with water and saturated aqueous NaCl,dried over anhydrous MgSO4 and concentrated in vacuo(508.7 mg). The residue was purified by using preparativeHPLC (column: L-Column2 ODS 20 mm ID¡Á150 mm L;mobile phase A: 0.1% TFA in water; mobile phase B: 0.1%TFA in acetonitrile; flow rate: 20 mL/min). The first elutingfactions (tR1) were concentrated to dryness, and washed withsaturated aqueous NaHCO3, extracted with EtOAc. The organic layer was separated, washed with water and saturatedaqueous NaCl, dried over anhydrous MgSO4 and concentratedin vacuo. The residue (42.7 mg) was crystallized from hexane-ethyl acetate to give 17 (34.4 mg, 0.072 mmol, 7.2%) asa white solid. 1H-NMR (300 MHz, DMSO-d6) delta: 1.04 (3H, s),1.37 (3H, s), 2.44 (3H, s), 4.87 (1H, d, J=8.3 Hz), 5.39 (1H, s),7.23-7.34 (2H, m), 7.48-7.58 (2H, m), 7.93 (1H, d, J=7.5 Hz),8.55 (1H, s), 8.88 (1H, d, J=0.8 Hz), 9.07 (1H, d, J=8.3 Hz),9.50 (1H, d, J=7.5 Hz). MS (ESI/APCI) m/z 476.2 [M+H]+.HPLC purity: 99.4%. mp 260C.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Mikami, Satoshi; Kawasaki, Masanori; Ikeda, Shuhei; Negoro, Nobuyuki; Nakamura, Shinji; Nomura, Izumi; Ashizawa, Tomoko; Kokubo, Hironori; Hoffman, Isaac Dylan; Zou, Hua; Oki, Hideyuki; Uchiyama, Noriko; Hiura, Yuuto; Miyamoto, Maki; Itou, Yuuki; Nakashima, Masato; Iwashita, Hiroki; Taniguchi, Takahiko; Chemical and Pharmaceutical Bulletin; vol. 65; 11; (2017); p. 1058 – 1077;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

N-Bromosuccinimide (5.89 g, 33.1 mmol) was added to a solution of 4-methyl-1H-1,2,3-triazole (2.50 g, 30.1 mmol) in chloroform (30 mL), and the reaction mixture was stirred for 16 hours at room temperature (15 C.). It was then diluted with dichloromethane (100 mL), washed with water (2¡Á100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to provide the product as a white solid (4.9 g), which was used directly in the next step.

Statistics shows that 27808-16-8 is playing an increasingly important role. we look forward to future research findings about 4-Methyl-1H-1,2,3-triazole.

Reference:
Patent; Pfizer Inc.; Galatsis, Paul; Henderson, Jaclyn Louise; Kormos, Bethany Lyn; Kurumbail, Ravi G.; Reese, Matthew Richard; Stepan, Antonia Friederike; Verhoest, Patrick Robert; Wager, Travis T.; Pettersson, Martin Youngjin; Garnsey, Michelle Renee; (150 pag.)US2017/73343; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics