Day: April 15, 2021

Synthetic Route of 1001401-62-2, 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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of A-I (0.72 g, 3.8 mmol) and thionyl chloride (0.36 mL, 5.0 mmol) in toluene (7.0 mL) and a drop of DMF is heated to 60C for 2h, then cooled and concentrated. The residue isdissolved in dry DCM (5 mL) and added dropwise to a stirred mixture of B-I (0.65 g, 4.64 mmol)and TEA (1.44 mL, 10.3 mmol) in dry DCM (10 mL) at 0C. The reaction is stirred at RTfor2h.Water is added and the organic layer is separated, washed with citric acid (10% aq. solution)and with NaHCO3 (sat. aq. solution). The organic layer is dried and concentrated to provide 0.94g of C-4. ESI-MS: 275 [M+H], HPLC (Rt): 0.69 mm (method M)

The chemical industry reduces the impact on the environment during synthesis 2-(2H-1,2,3-Triazol-2-yl)benzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; (65 pag.)WO2017/178339; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3 -methyl- IH-1, 2,4-triazole (2.20 g, 26.4 mmol), l,5-difluoro-2- methoxy-4-nitrobenzene (5.00 g, 26.4 mmol), and potassium carbonate (3.65 g, 26.4 mmol) in anhydrous DMSO (50 mL) was heated at 80 0C for 24 h. The reaction mixture was allowed to cool to rt and was poured into 500 mL of water/10 mL brine solution. The aqueous mixture was extracted with EtOAc (2 x 250 mL). The combined organic extracts were washed with water (500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel column chromatography (50% EtOAc/hexane) to afford l-(5-fluoro-2-methoxy-4-nitrophenyl)-3- methyl-lH-l,2,4-triazole (1.24 g, 18 % yield). LC-MS (M+H)+ = 253.2. 1H NMR (SOO MHz, CDCl3) delta ppm 8.95 (s, 1 H) 8.00 (d, J=I 1.60 Hz, 1 H) 7.80 (d, J=6.10 Hz, 1 H) 4.09 (s, 3 H) 2.50 (s, 3 H).

The synthetic route of 3-Methyl-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, III, Lorin A.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2011/14535; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 13273-53-5,Some common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, 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 mixture of 2-((4-chlorophenethyl)amino)-2-phenyl-l-(6-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-lH-indol-3-yl)ethan-l-one (0.06 g, 0.11 mmol), 4-bromo-l -methyl – 1H- 1,2, 3 -triazole (0.019 g, 0.11 mmol), and cesium carbonate (0.095 g, 0.29 mmol) in a mixture of 4:1 dioxane:water (5 ml) was degassed for 20 minutes with argon. S-Phos Pd precatalyst G3 (0.009 g, 0.01 mmol) was added and degassing was continued for another 10 minutes. The reaction mixture was heated in a sealed tube with microwave heating at 135 C for 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was treated with water (15 ml) and extracted with ethyl acetate (2 x 15 ml). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the title compound as solid (0.040 g, 74%) in racemic form.

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

Reference:
Patent; CONSTELLATION PHARMCEUTICALS, INC.; WILSON, Jonathan, E.; LEVELL, Julian, R.; (152 pag.)WO2019/161157; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 252742-72-6, These common heterocyclic compound, 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, 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.

Benzylmercaptan (1.75 mL; 14.9 mmol) was dissolved in DMF (20 mL) and solid K2CO3 (2. 35 g; 17 mmol) was added. To the resulting slurry was added a solution of 5-(chloromethyl)-2,4-dihydro-3H-1, 2,4-triazol-3-one (2.0 g; 15 mmol) in DMF (12 mL), prepared by a literature procedure (C. J. Cowden et. al., Tetrahedron Letters 41 (2000) 8661-8664). The reaction mixture was stirred at room temperature for 20.5 h. Water (80 mL) was added and a thick slurry was formed. The solid product was collected by filtration and washed with water. The remaining filtrate and wash liquid still contained product and was extracted four times with EtOAc, and the organic phase was then washed with water (twice), brine (twice) and dried (Na2SO4). Evaporation of solvents gave another crop of crude product. The combined solid materials were suspended in toluene and evaporated to remove water residues. The crude product was then suspended in a boiling mixture of EtOAc/heptane (1: 4) and allowed to cool before the solid product was collected by filtration. The subtitle compound was obtained as a colourless solid (2.03 g; 61percent yield). APCI-MS m/z: 222.1 [MH+]. ‘H-NMR (DMSO-D6): 8 11.35 (1H, vbrs), 11.26 (1H, brs), 7.37-7. 21 (5H, m), 3.72 (2H, s), 3.36 (2H, s) ppm. ‘3C-NMR (DMSO-D6): 8 156.09, 144.75, 137.66, 128.83, 128.23, 126.79, 34.75, 25.80 ppm.

Statistics shows that 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one is playing an increasingly important role. we look forward to future research findings about 252742-72-6.

Reference:
Patent; ASTRAZENECA AB; WO2005/95362; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1157938-97-0, 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 1157938-97-0 as follows.

(B) in a three neck reaction flask, propionitrile was added 4mol, 0.1mol catalyst (containing primary amine 0.05molC-9 cinchona alkaloids, 0.05mol formula and copper pigment base formula),Benzoic acid and 0.1mol 0.5LN, N- dimethylacetamide (the DMA), cooled to -10 , stirring the first solution containing 1mol product 0.3LN, N- dimethylacetamide solution, at -10 8 hours of reaction, TLC the reaction was complete, a solution of a concentration of 1mol / 0.3L L hydrochloric acid the reaction was quenched with 0.2L ethyl acetate three times, the combined organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, the resulting oil was treated with n-heptane / methylene chloride (1/1 by volume) was recrystallized, filtered and dried to give an off-white solid, i.e. a second product, yield 80%, dr is 97:3.;

According to the analysis of related databases, 1157938-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Ke; (7 pag.)CN105777740; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature 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.

[0789] lH-1,2,3-triazole-5-carboxylic acid (3.4 mg, 30f.tmol) was combined with HATU (11 mg, 30 f.tmol) in DMF(0.3 mL) and stirred at room temperature for 10 minutes;DIPEA (1 eq.) was added and the mixture was stirred for 1minute. Compound 2 (1 0 mg, 30 f.tmol) was dissolved in DMF(0.5 mL) and DIPEA (5.2 f.LL, 30 fllllOI) was added, followedby addition of the activated acid solution. The mixture wasstirred at room temperature for 30 minutes, after which timeLCMS indicated desired product formation. Half of the crudeproduct was purified using reverse phase chromatography toyield Compound a (7.7 mg) as a TFA salt. MS m/z [M+Hrcalc’d for C22H28CIFN60 3 , 539.19; found 539. Half of thecrude product was carried to the next step without furtherpurification.

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

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

Some common heterocyclic compound, 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, molecular formula is C8H7N3O2, 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. SDS of cas: 15988-11-1

General procedure: A mixture of malononitrile 1 (1 mmol), aldehyde 2(1 mmol), 4-phenylurazole 3 (1 mmol), and zeolite (0.05 g)was placed in a mortar. The reaction mixture was then heatedat 80 C for 60 min. After completion of the reaction as monitored by TLC analysis, the reaction mixture was cooled,and the solid was dissolved in acetone (15 mL), filtered and evaporated under vacuum to give the product, which was crystallized from ethanol to afford pure compound 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15988-11-1, its application will become more common.

Reference:
Article; Nejat, Razieh; Mahjoub, Mohammad Amin; Hekmatian, Zahra; Javidi, Mohammad Amin; Babashah, Sadegh; Journal of the Iranian Chemical Society; vol. 15; 5; (2018); p. 1133 – 1143;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 23579-79-5, 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. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

NH4Cl (150 mL) and extracted with EtOAc (250 mL). The layers were separated, and the aqueous layer extracted with further EtOAc 250 mL. The combined organics were dried over magnesium sulfate, filtered and reduced in-vacuo. The resultant solid was triturated with diethyl ether and filtered to give N-(5-bromo-2-methyl-1,2,4-triazol-3-yl)-4-cyclopropyl-1-tetrahydropyran-2-yl-indazol-5-amine (11.05 g, 26.5 mmol, 80% yield) as a cream solid. UPLC-MS (ES+, Method A): 1.65 min, m/z 417.3/419.3 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-1-methyl-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); 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., Formula: C3H3Br2N3

In a 50 mL pressure vial, 3,5-dibromo-1-methyl-1H-1,2,4-triazole (Int-41, 1.47 g, 6.1 mmol) was dissolved in DMF (13 mL) and potassium carbonate (1.53 mg, 11.1 mmol), followed by 3-fluoro-5-methylphenol (700 mg, 5.55 mmol) were added. The vial was sealed, the reaction mixture was stirred for 15 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 25:75 v/v) to yield the title compound as light yellow solid (1.23 g, 75%). 1H NMR (CDCl3, 300 MHz): delta 2.38 (s, 3 H), 3.77 (s, 3 H), 6.76-6.82 (m, 1 H), 6.84-6.91 (m, 2 H). MS (ES+) m/z 286.0, 288.0 [M+H, Br isotopes] .

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 60166-43-0, 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. 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.

In a pressure vessel equipped with a magnetic stirring bar was added 3-bromo-7- chloro-5-((4,4-difluorocyclohexyl)(phenyl)methyl)-5H-pyrrolo[2,3-b:4,5-b’]dipyridine (240 mg, 0.489 mmol), l ,4-dimethyl-lH-l ,2,3-triazole (52.2 mg, 0.538 mmol) and DMF (5 mL). Tetramethylammonium acetate (98 mg, 0.734 mmol) and PdCl2(dppf)-CH2Cl2 adduct (28.0 mg, 0.034 mmol) was added. Argon was bubbled into the mixture with sonication for 5 min, then the vessel was capped, placed into a preheated aluminum block set at 100C and was stirred for 16 h. Solids were filtered, and the filtrate was purified by preparative HPLC (20-100% B; B solvent 90% MeCN/0.1% TFA water, Phenomenex LUNA C18 30xl00mm, 10 micron, 30 mL/min flow rate, 254nm UV; Rt = 1 1.6 min.). Like fractions were concentrated and re-purified by preparative HPLC: Column: Waters XBridge C 18, 19 x 200 mm, 5-mupiiota particles; Mobile Phase A: 5 :95 methanol: water with lOmM NH40Ac; Mobile Phase B: 95:5 methanol: water with lOmM NFLtOAc; Gradient: 40-80% 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 to give 18 mg of a mixture of enantiomers. This material was subject to a chiral purification: Chiral SFC conditions: Chiralcel OJ-H preparative column, 30 x 250mm, 5muiotaeta; Mobile Phase: 15% methanol in CO2, 150 bar; Temp: 35C; Flow rate: 70.0 mL/min. for 25 min. ; UV monitored at 254nm; Injection: 0.25ml of ~9 mg/mL solution in MeOH (18 mg purified by stacked injection); Rt = isomer A: 13.8 min. ; isomer B: 18.3 min. Fractions containing the desired products were combined and dried via evaporation to give 6.9 mg (2%) of the isomer A with an average purity by LC/MS analysis was >99%. Fractions containing the desired products were combined and dried via evaporation to give 7.5 mg (3%) of the isomer B with an average purity by LC/MS analysis was >99%. Isomer A: Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7muetaiota particles; Mobile Phase A: 5:95 ACN:water with 10 mM NlrUOAc; 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 = 1.76 min.; LC/MS (M+H) = 568.7. Injection 2 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-muetaiota particles; Mobile Phase A: 5:95 methanol: water with 10 mM NFL Ac; Mobile Phase B: 95:5 methanol: water with 10 mM NFL Ac; 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= 2.77 min.; LC/MS (M+H) = 568.7. Isomer B: Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7mupiiota particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM MLtOAc; 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= 1.86 min.; LC/MS (M+H) = 568.7. 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 MLtOAc; Mobile Phase B: 95:5 methanol: water with 10 mM MLtOAc; 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= 2.73 min.; LC/MS (M+H) = 568.7. NMR (500MHz, DMSO-c e) delta 8.82 (d, J=8.1 Hz, 1H), 8.67 (s, 1H), 8.54 (br. s., 1H), 7.73 (d, J=8.1 Hz, 3H), 7.32 (t, J=7.5 Hz, 2H), 7.25 (t, J=7.3 Hz, 1H), 6.09 (br. s., 1H), 4.36 (s, 3H), 4.02 (s, 3H), 3.52 (br. s., 1H), 2.30 (s, 3H), 2.07 (br. s., 1H), 1.92 (d, J=7.3 Hz, 1H), 1.82 (br. s., 1H), 1.73 (br. s., 1H), 1.66 (br. s., 1H), 1.45 (d, J=12.1 Hz, 1H), 1.37 (br. s., 1H), 1.30 (d, J=11.7 Hz, 1H). LC/MS (M+H) = 568.2; HPLC conditions: Rt= 0.93 min. (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: 40C; Gradient: 2-98% B over 1.5 min; Flow: 0.8 mL/min).

The synthetic route of 1,4-Dimethyl-1H-1,2,3-triazole has been constantly updated, and we look forward to future research findings.

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