Day: May 25, 2021

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

Into a macrowave tube, 4-methyl-1 H-1 ,2,3-triazole (473 mg, 5.69 mmol) was dissolved in THF (10 ml) and cooled to 0C, NaH (341 mg, 8.54 mmol) was added and stirred for 1 h at rt. A solution of 4-(4-methoxyphenyl)butyl methanesulfonate (490 mg, 1.897 mmol) in DMF (2.00 ml) and THF (1.0 ml) was then added and heated to 60C for 3h. The mixture was diluted with EA (20 ml) and filtered through a pad of celite. The filtrate was concentrated to dryness. The crude was purified using ISCO column (DCM to 40% EA in DCM) to give two isomers. The title compound (0.13 g), 1H NMR (400 MHz, CDCb) delta ppm 1.57 – 1.64 (m, 2 H) 1.88 – 2.02 (m, 2 H) 2.29 (s, 2 H) 2.57 (t, J=7.63 Hz, 2 H) 3.78 (s, 3 H) 4.35 (t, J=7.04 Hz, 2 H) 6.76 – 6.86 (m, 2 H) 7.06 (m, J=8.22 Hz, 2 H) 7.31 (s, 1 H) and 2-(4-(4-methoxyphenyl)butyl)-4-methyl-2H-1 ,2,3-triazole (0.18 g). 1H NMR (400 MHz, CDCb) delta ppm 1.60 – 1.68 (m, 2 H) 1.80 – 1.97 (m, 2 H) 2.26 (s, 1 H) 2.33 (s, 2 H) 2.52 – 2.66 (m, 2 H) 3.78 (s, 3 H) 4.16 – 4.36 (m, 2 H) 6.82 (m, J=8.22 Hz, 2 H) 7.05 (d, J=8.61 Hz, 2 H) 7.32 (m, 1 H)

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

Reference:
Patent; UNIVERSITE DE MONTREAL; GAREAU, Yves; GINGRAS, Stephane; CHANTIGNY, Yves; YANG, Gaoqiang; SAUVAGEAU, Guy; BACCELLI, Irene; MARINIER, Anne; (284 pag.)WO2019/84662; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 27996-86-7,Some common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, molecular formula is C9H7N3O, 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.

General procedure: The general procedure for the synthesis of the N-heterocycles using SnAP reagents was as follows. To a solution of the aminotributylstannane-SnAP reagent (0.50 mmol, 1.00 equiv.) in CH2Cl2 (2.5 ml) was added the corresponding aldehyde (0.50 mmol, 1.00 equiv.) and molecular sieve (MS) 4A (50 mg) under an inertat mosphere at r.t. The reaction mixture was stirred for two hours and filtered through a layer of Celite (0.3 cm), rinsing with CH2Cl2. The filtrate was concentrated under reduced pressure to afford the imine. Separately, anhydrous Cu(OTf)2 (0.50 mmol, 1.00 equiv.) was added to as olution of 2,6-lutidine (0.50 mmol, 1.00 equiv.) in HFIP (2.0 ml) in a dry Schlenk flask and stirred at r.t. for one hour, during which a homogeneous suspension formed. A solution of the imine (0.50 mmol, 1.00 equiv.) in dry CH2Cl2 (8.0 ml) was added in one portion and the resulting mixture was allowed to stir at r.t. for 12 hours (unoptimized reaction time). The reaction was quenched at r.t. with a mixture ofsaturated aqueous NaHCO3 (4 ml) and 10% aqueous NH4OH (2 ml). The mixturewas stirred vigorously for 15 minutes, the layers were separated and the aqueous layer was extracted with CH2Cl2 (3 × 5 ml). The combined organic layers were washed with H2O (3 ×5 ml) and brine (10 ml), dried over Na2SO4, filtered, concentrated and purified by flash column chromatography on silica gel using a precolumn of KF (3 cm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-[1,2,4]Triazol-1-yl-benzaldehyde, its application will become more common.

Reference:
Article; Vo, Cam-Van T.; Luescher, Michael U.; Bode, Jeffrey W.; Nature Chemistry; vol. 6; 4; (2014); p. 310 – 314;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 60166-43-0, The chemical industry reduces the impact on the environment during synthesis 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

(R)-3-Bromo-7-chloro-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrrolo[2,3-b:4,5-b’]dipyridine (30.0 mg, 0.066 mmol), l,4-dimethyl-lH-l,2,3-triazole (25.5 mg, 0.263 mmol), Me4NOAc (21.8 mg, 0.164 mmol), and PdCl2(dppf)2.DCM (3.8 mg, 4.60 muetaiotaomicron) were weighed into a 20 mL scintillation vial, and 3 mL DMF was added and the air was replaced with nitrogen. The reaction mixture was heated to 100 C with stirring. After 1 h, it was cooled to room temperature, filtered, and concentrated. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19 x 200 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 ACN: water with 10-mM NH4OAc; Mobile Phase B: 95:5 ACN: water with 10-mM NH4OAc; Gradient: 20-60% B over 15 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. The yield of the product was 4.2 mg, and its estimated purity by LC/MS analysis was 100%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-muetaiota particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50 C; 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 = 1.52 min, LC/MS (M+H) = 534.5, LC/MS (M+H) = 534.5. Injection 2 conditions: Column: Waters BEH CI 8, 2.0 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 methanol: water with 10 mM NH4OAc; Mobile Phase B: 95:5 methanol: water with 10 mM NH4OAc; Temperature: 50 C; 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 = 2.50 min, LC/MS (M+H) = 534.5. NMR (500MHz, DMSO-c e) delta 8.82 (d, J=8.1 Hz, 1H), 8.67 (s, 1H), 8.58 (br. s., 1H), 7.74 (t, J=7.2 Hz, 3H), 7.36 – 7.28 (m, 2H), 7.28 – 7.20 (m, 1H), 6.07 (br. s., 1H), 4.39 (s, 3H), 4.03 (s, 3H), 3.89 (d, J=13.6 Hz, 1H), 3.75 (d, J=9.9 Hz, 1H), 3.61 (br. s., 1H), 3.43 (t, .7=11.2 Hz, 1H), 3.24 (t, .7=11.4 Hz, 1H), 2.55 (s, 3H), 2.31 (s, 3H), 1.62 (br. s., 1H), 1.51 – 1.39 (m, 1H), 1.29 (d, J=8.4 Hz, 1H), 1.15 (br. s., 1H); LC/MS (M+H) = 534.3 [Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7u; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: ACN with 0.05% TFA; Temperature: 40 C; Gradient: 2-98% B over 1.5 min; Flow: 0.8 rnL/min].

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, 1,4-Dimethyl-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

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

Application of 118863-62-0,Some common heterocyclic compound, 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, molecular formula is C8H6BrN3, 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.

A solution of 3-(4-bromophenyl)-lH-l,2,4-triazole (10.9 g, 48.5 mmol), l-iodo-4-(trifluoromethoxy)benzene (13.2 g, 45.8 mmol), copper(I) iodide (2.38 g, 12.5 mmol), and cesium carbonate (30.3 g, 93.0 mmol) in dimethylsulfoxide (85 mL) was degassed with nitrogen for 5 minutes. The mixture was heated at 100 C for 60 hours. After cooling, ethyl acetate (200 mL) was added and the mixture was filtered through Celite. The filtrate was added to a solution of saturated ammonium chloride (200 mL) and stirred for one and a half hours. The layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and adsorbed onto Celite. Purification by flash column chromatography using 0-40% ethyl acetate/hexanes as eluent provided the title molecule as an off-white solid (9.65 g, 52%) : mp 109-112 C; XH NMR (400 MHz, CDCI3) delta 8.56 (s, 1H), 8.10-8.03 (m, 2H), 7.83-7.75 (m, 2H), 7.64-7.57 (m, 2H), 7.42-7.35 (m, 2H); ESIMS m/z 384 ([M + H]+).

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

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; BAUM, Erich W.; FISCHER, Lindsey G.; GOLDSMITH, Miriam E.; CROUSE, Gary D.; RENGA, James M.; SPARKS, Thomas C.; (234 pag.)WO2016/99929; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, 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 202931-88-2, Recommanded Product: 202931-88-2

6-bromo-4-chloro-2-methoxy-3 – (4 – (trifluoromethyl) benzyl) quinoline (1.45 g, 3.37 mmol, Intermediate 10: step d) comprises that the flask, THF (25 was added to mL), the solution was cooled to -75 .n-BuLi (dropwise 2.5 M, 1.3 mL, 3.25 mmol )in hexane.After 2 minutes, 3 mL of THF 1 -methyl -1H-1,2,3-triazole-5-carbaldehyde (580 mg, 5.22 mmol, Intermediate 18) was introduced.The reaction mixture was warmed to -20 over 45 minutes and, at this time the reaction NH4was quenched with aqueous solution of Cl.Extract the aqueous portion with EtOAc (5 × 40 mL), washing the combined organics with brine, MgSO4dried over, filtered and concentrated.Silica gel (5% CH3CN-DCM, 30% CH3by chromatography on increased to CN + 2% MeOH), to give the title compound as a pale yellow non-crystalline solid.

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; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 16681-70-2,Some common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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 stirred solution of ( 5,^5)-4-amino-5-biphenyl-4-yl-2-ethoxymethylpentanoic acid ethyl ester (17 mg, 47 muiotaetaomicron) in DMF (0.3 mL), was added lH-l,2,3-triazole-4- carboxylic acid (5.3 mg, 47 muiotaetaomicron) and HATU (18 mg, 47 muiotaetaomicron), followed by DIPEA (25 mu^, 141 muiotaetaomicron). The mixture was stirred for 30 minutes, then concentrated under reduced pressure to yield crude Co step without purification.

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); 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. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3,5-Dibromo-1-methyl-1H-1,2,4-triazole

Intermediate 8 3-Bromo-l-methyl-5-(2-phenylazetidin iazole 3,5-Dibromo-l-methyl-lH-l,2,4-triazole (200 mg, 0.83 mmol) and 2-phenylazetidine (177 mg, 1.33 mmol) were dissolved in DMF (5 mL). Potassium carbonate (344 mg, 2.49 mmol) was added. The mixture was heated at 170C for 2 hour in a microwave reactor. The mixture was cooled to rt, diluted with water and extracted with diisopropyl ether. The organic layer was washed with brine and dried over sodium sulfate. The solvents were removed to give the title compound as a liquid (225 mg, 92%). MS (ESI+) m/z 294 [M+H]+. XH NMR (400 MHz, CDCI3) delta ppm 2.37 – 2.49 (m, 1 H) 2.71 – 2.82 (m, H) 3.39 (s, 3 H) 4.11 – 4.19 (m, 2 H) 5.38 (t, 1 H) 7.28 – 7.48 (m, 6 H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

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

Synthetic Route of 288-36-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 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.

A solution of 2-bromo-3-thiophene carboxylic acid (1.50 g, 7.24 mmol), 1H-1,2,3- triazole (0.600 g, 8.69 mmol), potassium carbonate (2.00 g, 14.5 mmol), and copper iodide (0.138 g, 0.724 mmol) in DMF (36.2 mL) was purged subsurface with nitrogen and heated to 75 C for 96 h. The reaction was diluted with water, washed with ether, and acidified with cone. HC1. The acidic aqueous solution was extracted 3x with EtOAc and the combined organic fractions were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel gradient chromatography [0-70% (1% acetic acid in EtOAc) in hexanes], to provide Intermediate C as a solid. LRMS m/z (M+H) 196.2 found, 196.1 required.

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, 1H-1,2,3-Triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (0 pag.)WO2016/85784; (2016); 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. 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-[1,2,4]Triazol-1-yl-benzaldehyde

Amixture of 1,10-phenanthroline-5,6-dione (6.1 mmol, 1.30 g) and 4-(1H-1,2,4-triazol-1-yl)benzaldehyde (5.7 mmol, 1.00 g), ammonium acetate (90 mmol, 6.90 g) and glacialacetic acid (90 mL) was refluxed for about 6 h, then cooled to room temperature anddiluted with water (ca. 50 mL). To the obtained orange-red solution, concentrated aqueousammonia was added dropwise until pH 6; the yellow product (1.75 g, yield: 84.5%)was collected by filtration and washed with water several times. m/z: 364.1 (supplementarymaterial Figure S13). 1H NMR (CD3)2SO, 400 MHz also confirms the structure of ligand(supplementary material Figure S14). IR (KBr, cm1): 3468, 3417, 3117, 1638, 1615, 1528,1508, 1486, 1455, 1400, 1280, 1222, 1145, 1073, 983, 840, 803, 738, 670, 618.

According to the analysis of related databases, 27996-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Wei; Li, Lin-Shen; Zhong, Ri-Ming; Cai, Dan-Ju; Zhan, Qiu-Qiang; Lin, Wei-Quan; Zhang, Ze-Min; Wu, Jian-Zhong; Ou, Yong-Cong; Journal of Coordination Chemistry; vol. 72; 11; (2019); p. 1865 – 1875;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 13423-60-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 13423-60-4 as follows.

EXAMPLE 115 1-phenyl-4-(undec-1-yl)triazolium bromide 0.300 g (0.002 mol) 1-phenyltriazole 1 and 1.41 g (0.006 mol) 1-bromoundecane 2 are combined in a pressure tube. The reaction mixture is stirred for 24 h at 110 C. The reaction mixture is cooled down and the same volume petroleum ether is added. The precipitated solid is filtered off, washed with petroleum ether/THF (1:1), and is dried in HV. M 380.37 C19H30N3N3Br Yield: 0.281 g (37%) 1H-NMR DM-187 (300 MHz/DMSO):

According to the analysis of related databases, 13423-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TECHNISCHE UNIVERSITAET DRESDEN; US2011/105761; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics