Month: August 2021

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. 67545-00-0, name is 4-Amino-1-methyl-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H6N4

A solution of (2S,3S)-2-(fluoromethyl)-7-(methylcarbamoyl)-3-phenyl-2,3-d ihydrobenzofuran5-carboxylic acid (80 mg, 0.24 minol) and HATU (111 mg, 0.292 minol) in DMSO (0.85 mL) was treated at rt with DIPEA (0.127 mL, 0.729 minol) and the reaction minxture was stirred at this temperature for 5 min then was treated with 1-methyl-1H-1,2,3-triazol-4-amine (23.8 mg, 0.243minol). The resulting minxture was stirred for 1 h at rt. Further HATU (111 mg, 0.292 minol) and DIPEA (0.127 mL, 0.729 minol) were then added and the reaction minxture left to stir at rt for 5 min before being treated with 1-methyl-1H-1,2,3-triazol-4-amine (23.8 mg, 0.243 minol). The reaction minxture was then stirred for 1 h at rt then was left to stand over the weekend. It was then purified by MDAP (method high pH) to give (2S,3S)-2-(fluoromethyl)-N7-methyl-N5-(1-methyl- 1H- 1,2,3-triazol-4-yl)-3-phenyl-2,3-dihydrobenzofuran-5,7-dicarboxaminde (69.5 mg, 70%) as a yellow solid. LCMS (method forminc): Retention time 0.89 min [M+H] = 410

If you are hungry for even more, make sure to check my other article about 67545-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen, John; DEMONT, Emmanuel, Hubert; HARRISON, Lee, Andrew; PRESTON, Alexander, G.; SEAL, Jonathan, Thomas; WALL, Ian, David; WATSON, Robert, J.; WOOLVEN, James, Michael; (214 pag.)WO2017/174620; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 6523-49-5, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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.

4-Chloro-6-iodoquinazoline (WO9609294 Al , 150 mg) was treated with 4- triazolyl aniline (28 mg, 1 eq) in MeCN and refluxed for 6 h. Cooled overnight and filtered to give the title compound (70 mg).1R NMR delta 11.75 (IH, br s), 9.4 (2H, s), 9.04 (IH, s), 8.43 (IH, d, J 8.85Hz),8.34 (IH, s), 8.0(4H, m), 7.82 (IH, d, J 8.85Hz); LC-MS rt 2.32 m/z 415 ES+.

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 4-(1,2,4-Triazol-1-yl)aniline is helpful to your research.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 4928-87-4, 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. 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.

Compound 1 was prepared using the branched tube method [11]: 1H-1,2,4-triazole-3-carboxylic acid (0.117 g, 1 mmol), potassium iodide (0.166 g, 1 mmol) and lead(II) nitrate (0.331 g, 1 mmol) were placed in the arm to be heated. Water was carefully added to fill both arms, and then the arm to be heated was placed in a bath at 60 C. After 10 days, yellow crystals were deposited in the cooler arm which were filtered off, washed with water and air dried. (0.28 g, yield 63%), m.p. > 300 C. Anal. Calc. for C3H2IN3O2Pb: C, 8.07; H, 0.45; N, 9.41. Found: C, 8.15; H, 0.43; N, 9.63%. IR (cm-1) selected bands: 810(m), 981(m), 1280(m), 1453(vs), 1622(vs), 3102(br) and 3444(br).

Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 1,2,4-Triazole-3-carboxylic acid.

Reference:
Article; Safarifard, Vahid; Morsali, Ali; Inorganica Chimica Acta; vol. 398; (2013); p. 151 – 157;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7411-23-6, New Advances in Chemical Research in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 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.

EXAMPLE 1Preparation of 2-(3,5-dibromo-1H-1,2,4-triazol-1-yl)-1-(2,4-difluorophenyl)ethan-1-oneFirst, 43.7 g of 3,5-dibromo-1H-1,2,4-triazole is introduced into 200 mL of tetrahydrofuran (THF), the resultant mixture is agitated, and 40.4 g of 2-chloro-2,4-difluoroacetophenone is further introduced thereto. Next, 36.3 g of potassium carbonate is introduced to the reaction mixture and the resultant mixture is agitated for 7 hours at room temperature. After the completion of the reaction, the reaction mixture is filtered, washed with 100 mL of tetrahydrofuran (THF), and concentrated at room temperature. Then, 437 mL of purified water is introduced so that the crystals are slurried, followed by filtering. The filtered crystals are reslurried in 175 mL of isopropanol and filtered again. The crystals are washed with 44 mL of isopropanol and dried with hot air at 50 C. to obtain 63.8 g of the title compound as a white solid (yield 87%, purity 99.2%, HPLC, detected at a wavelength of 256 nm, 18C 4.6×250 mm, mobile phase 60% ACN, flow rate 1 mL/min).1H-NMR (200 MHz, CDCl3) delta (ppm): 8.118.03(1H), 7.11-6.96(2H), 5.51(2H).

By the way, if you are interested in learning more fun chemistry with your kids, get your hands into one chemistry set now, and start enjoying the best part of chemistry: experiments about 3,5-Dibromo-1H-1,2,4-triazole.

Reference:
Patent; Dongkook Pharmaceutical Co., Ltd.; US2013/5973; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic. 1338226-21-3, name is 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. name: 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one

To 5-tert-butyl-2-chloro-4-hydroxy-benzonitrile (2.29 g, 10.9 mmol) in N-methyl-pyrrolidinone(55 mL) was added NaH (568 mg, 14.2 mmol). The mixture was stirred at room temperature for30 mi 3-(Chloromethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one (1.93 g, 13.11 mmol) wasdissolved in N-methyl-pyrrolidinone (20 mL) and added dropwise via addition funnel over 30 mm. Upon complete addition, water (160 mL) was slowly added to the reaction. After stirring until cooled to room temperature, the reaction was filtered and solids dried to give 3.15 g of the title compound as a white solid (90% yield). MS (mlz): 321.5 [M+H].

In conclusion, we affirm that quantitative kinetic descriptions of catalytic behavior continue to serve as an indispensable tool to navigate research efforts intended to model. Read on for other articles about 1338226-21-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); 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. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 60166-43-0

In a 75 mL pressure vessel equipped with a magnetic stirring bar, was added (5)- 3-bromo-7-chloro-5-((2-fluorophenyl)(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrrolo[2,3- b:4,5-b’]dipyridine (650 mg, 1.37 mmol), l,4-dimethyl-lH-l,2,3-triazole (199 mg, 2.05 mmol) and NMP (10 mL). Tetramethyl NH4OAC (274 mg, 2.05 mmol) and bis(triphenylphosphine) palladium(II) chloride (67.3 mg, 0.096 mmol) was added. Argon was bubbled into the mixture with sonication for 5 min, then the vessel was capped and placed into a preheated oil bath at 100C. The reaction mixture was stirred overnight. Most of the solvent was removed under a stream of nitrogen while heating for several hours in an oil bath set at 100C. The remaining mixture was taken up in 2 mL of DMF then filtered for purification by preparative HPLC: Column: Waters XBridge CI 8, 19 x 200 mm, 5-muiotatauiota particles; Mobile Phase A: 5:95 methanol: water with lOmM NLUOAc; Mobile Phase B: 95:5 methanol: water with lOmM NHtOAc; Gradient: 10-80% B over 30 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 4.7 mg (0.6%) of the title compound with an average purity by LC/MS analysis was >99%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7um particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm. Rt= 1.50 min; LC/MS (M+H) = 552.5. Injection 2 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-mupiiota particles; Mobile Phase A: 5:95 methanol: water with 10 mM NFL Ac; Mobile Phase B: 95:5 methanol: water with 10 mM NH4OAc; Temperature: 50C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 0.5 mL/min; Detection: UV at 220 nm. Rt= 2.51 min; LC/MS (M+H) = 552.5. NMR (500MHz, DMSO-c e) delta 8.81 (d, J=8.1 Hz, 1H), 8.68 (s, 1H), 8.46 (br. s., 1H), 8.20 (br. s., 1H), 7.71 (d, J=8.1 Hz, 1H), 7.34 (d, J=5.5 Hz, 1H), 7.29 (d, J=7.7 Hz, 1H), 7.17 – 7.04 (m, 1H), 6.36 (br. s., 1H), 4.34 (br. s., 3H), 4.00 (br. s., 3H), 3.93 – 3.83 (m, 1H), 3.72 (d, J=9.5 Hz, 1H), 3.47 – 3.38 (m, 4H), 3.27 – 3.15 (m, 1H), 2.29 (br. s., 3H), 1.72 (d, J=11.7 Hz, 1H), 1.58 – 1.42 (m, 1H), 1.33 (d, J=12.1 Hz, 1H), 0.98 (d, J=13.2 Hz, 1H). LC/MS (M+H) = 552.5; HPLC conditions: Rt= 2.57 min (Phenomenex LUNA C18 2 x 50 mm (4 min grad) eluting with 5-95% aq ACN containing lOmM NH4OAC, 0.8 mL/min, monitoring at 254 nm); Temperature: 40C).

If you are hungry for even more, make sure to check my other article about 60166-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature 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.

10818] To 2-(2H-1,2,3-triazol-2-yl)benzoic acid (125 g, 0.6 mmol) and DMF (4 mE) was added (i-Pr)2NEt (0.23 mE, 1.3 mmol) and HBTU (155 g, 0.6 mmol). Afier 10 mm, the title compound from step B (146 g, 0.4 mmol) was added. After stirring overnight at it, saturated NaHCO3 (aq.) was added and the mixture extracted with EtOAc (3x). The combined organics were dried (Mg504) and concentrated. Purification via preparative HPEC gave the title compound (89 mg, 47%) as a beige solid. MS (ESI) mass calcd. for C2QH18F3N70, 429.2; mlz found 430 [M+H]. 1H NMR (DMSO-D5): 8.47 (s, 0.3H), 8.24 (s, 0.7H), 8.14-8.05 (m, 2.2H), 8.02 (s, 0.7H), 7.85 (d, J=7.2 Hz, 1.3H), 7.72-7.55 (m, 1.7H), 7.49-7.34 (m, 1.4H), 7.13 (t, J=7.4 Hz, 0.7H), 4.58 (t, J4.3 Hz, 0.7H), 4.44 (d, J=4.7 Hz, 0.3H), 4.04-3.93 (m, 0.3H), 3.82 (t, J=4.1 Hz, 0.3H), 3.79-3.70 (m, 0.7H), 3.54 (d, J4.8 Hz, 0.7H), 2.07-1.90 (m, 1H), 1.85-1.07 (m, 5H).

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 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; COATE, Heather R.; DVORAK, Curt A.; FITZGERALD, Anne E.; LEBOLD, Terry P.; PREVILLE, Cathy; SHIREMAN, Brock T.; (473 pag.)US2016/46640; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7343-34-2, 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. 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, molecular formula is C4H7N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

4-chloro-6-(3,5-dimethyl-lH-l,2,4-triazol-l-yl)-2-methylpyrimidine (1-2) To a slurry of 4,6-dichloro-2-methylpyrimidine (1-1) (5.00 g, 30.7 mmol) and cesium carbonate (15.0 g, 46 mmol) in DMF (250 mL) at 0 °C was added a solution of 3,5-dimethyl-lH- 1,2,4- triazole (2.98 g, 30.7 mmol) in DMF (50 mL) via a dropping funnel over 1 h. The reaction was then warmed to room temperature and stirred for 1 h. The reaction was quenched by addition of water (500 mL) and extracted with ethyl acetate (3 x 400 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (0-30percent EtOAc/hexanes) to afford 4-chloro-6-(3,5-dimethyl-lH- l,2,4-triazol-l-yl)-2-methylpyrimidine (1-2) as a white solid. XH NMR (400 MHz, CDC13) delta 7.75 (s, 1H), 2.91 (s, 3H), 2.72 (s, 3H), 2.41 (s, 3H); MS mlz = 224 (M+H).

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 7343-34-2.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas, C.; JOHNSON, Adam, W.; KUDUK, Scott, D.; REGER, Thomas, S.; WO2014/78217; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1001401-62-2, New Advances in Chemical Research in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 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.

A solution of2-(2H-1,2,3-triazol-2-yl)benzoic acid (P. Coleman, J. Schreier,W02007/126934) (1 g, 4.1 mmol) in SOCb (10 mL) was stirred at 80 C for 30 min. Thesolvent was removed under reduced pressure and toluene (10 mL) was added to give solution A.The product from step 4 (1 g, 4.1 mmol) was dissolved in DCM (10 mL), DIEA (1.58 g, 1225 mmol) added, and then solution A added at 0 C. The resulting mixture was stirred at RT for 2 h,then poured into water (10 mL) and extracted with DCM (10 mL x 3). The combined organiclayers were washed with brine (10 mL), dried overNa2S04, filtered and concentrated in vacuo.The residue was purified by chromatography on silica (petroleum ether : EtOAc = 10 : 1 to = 3 :1) then purified by prep. TLC (petroleum ether: EtOAc = 1 : 1) to give the title compound (0.230 g). LRMS m/z (M+H) 416.0, 418.0 found, 416.1, 418.1 required

We very much hope you enjoy reading the articles and that you will join us to present your own research about 1001401-62-2, Happy reading!

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/18029; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 1533519-85-5, 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. 1533519-85-5, name is Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, molecular formula is C18H17N3O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

32 g of methyl 2-(4-(4-cyclopropyl-1-naphthyl)-4hydro-1,2,4-triazol-3-ylsulfanyl)acetate are placedIn a 10L flask, 600 mL of acetonitrile and 20 mL of pyridine were added, and the mixture was stirred and dissolved. After the solution was completely dissolved, the mixture was dropped at a rate of 10 mL/min.90mL of a 1mol/L Bromine Br2-acetonitrile solution was added dropwise at room temperature for 2 hours. After the reaction was complete, 2L of B was added to the reaction.Ethyl acetate was dissolved, washed twice with saturated brine, and washed with 1 L each time. The organic phase was collected and dried over saturated sodium sulfate.Concentrate and filter to obtain methyl 2-(5-bromo-4-(4-cyclopropyl-1-naphthyl)-4hydro-1,2,4triazol-3-ylsulfanyl)acetate.34.5 g, yield 87.3%; purity 98.2%.

I am very proud of our efforts over the past few months and hope to Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate help many people in the next few years.

Reference:
Patent; Chengdu Meiyugao Pharmaceutical Co., Ltd.; Wang Chunyan; Chen Zhiyong; Sui Yumin; (17 pag.)CN107955029; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics