Triazoles

61-82-5,Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61-82-5, its application will become more common.

Reference:
Article; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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 6523-49-5. 6523-49-5

General procedure: An aqueous solution of cesium carbonate (130 mg, 0.4 mmol) in water (300 ul) was dispensed into each well containing a pre-mixed solution of 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (58.8 mg, 0.2mmol), respective aniline (0.26 mmol), xantphos (13.9 mg, 0.024mmol) and palladium (II) acetate (3.6 mg, 0.016 mmol) in DMA (1.25 ml). The resultant plate was placed on a pre-heated SOPHAS base plate set at 150 oC and shaken for 1 hour. The plate was cooled to room temperature and MP-TMT resin (90 mg) added to each well prior to shaking overnight at room temperature. The following day each well was transferred to a 48 well filter plate, washing through with an extra aliquot of DMA (200 ul) before a final centrifuge. The crude filtrates were then purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5mu silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford required N2-(4-methoxyphenyl)-N4-[aryl]pyridine-2,4-diamine (23-42%) N2-(4-methoxyphenyl)-N4-[4-(1,2,4-triazol-1-yl)phenyl]pyridine-2,4-diamine (5a) 28%, LCMS (tR = 2.49 min., purity = 100%), ESI+ m/z, 359.08 (M+H)+; 1H NMR (DMSO-d6, 500 MHz): delta 9.20 (1H, s); 8.72 (1H, s), 8.50 (1H, s), 8.20 (1H, s), 7.85 (1H, m), 7.78 (2H, m), 7.49 (2H, m), 7.32 (2H, m), 6.85 (2H, m), 6.45 (1H, s), 6.35 (1H, m), 3.72 (3H, s); 13C NMR (176 MHz, DMSO-d6) delta 157.53, 153.44, 152.03, 150.31, 147.99, 141.77, 140.89, 135.27, 130.70, 120.65, 120.15, 120.01, 113.79, 103.08, 92.70, 55.11; HRMS m/z (ESI+) calculated for C20H18ON6, 359.16149; found: 359.16107.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-(1,2,4-Triazol-1-yl)aniline.

Reference:
Article; Burton, Rebecca J.; Crowther, Mandy L.; Fazakerley, Neal M.; Fillery, Shaun M.; Hayter, Barry M.; Kettle, Jason G.; McMillan, Caroline A.; Perkins, Paula; Robins, Peter; Smith, Peter M.; Williams, Emma J.; Wrigley, Gail L.; Tetrahedron Letters; vol. 54; 50; (2013); p. 6900 – 6904;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

252742-72-6, Adding a certain compound to certain chemical reactions, such as: 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, 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 252742-72-6.

Example 405 5-(4-(2-Fluorophenoxymethyl)piperidino]methyl-2,4-dihydro-[1,2,4]triazol-3-one After adding 150 mg of 5-chloromethyl-2,4-dihydro-[1,2,4]triazol-3-one, 331 mg of 4-(2-fluorophenoxymethyl)piperidine hydrochloride and 180 mg of anhydrous potassium carbonate to acetonitrile, the mixture was stirred overnight at room temperature. Water and ethyl acetate were added to the reaction mixture and the insoluble portion was filtered out to obtain the title compound (70 mg, 21percent yield). 1H-NMR (400 MHz, DMSO-d6); delta (ppm) 1.26-1.38 (2H, m), 1.67-1.80 (3H, m), 1.95-2.04 (2H, m), 2.77-2.84 (2H, m), 3.24 (2H, s), 3.88 (2H, d, J=5.6 Hz), 6.87-6.94 (1H, m), 7.06-7.21 (3H, m), 11.19 (1H, s), 11.27 (1H, br s).

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, 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ozaki, Fumihiro; Ono, Mutsuko; Kawano, Koki; Norimine, Yoshihiko; Onogi, Tatsuhiro; Yoshinaga, Takashi; Kobayashi, Kiyoaki; Suzuki, Hiroyuki; Minami, Hiroe; Sawada, Kohei; US2004/167224; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-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 16681-65-5, 16681-65-5

To a flask containing 1-methyl-1H-1,2,3-triazole (250 mg, 3.01 mmol) was added THF (20 mL) and the solution was cooled to -45 C. using a CH3CN-CO2 bath. n-BuLi (2.5 M in hexanes, 1.2 mL, 3 mmol) was added dropwise which produced an opaque suspension. The suspension was stirred at -45 C. for 20 minutes, then a homogeneous solution of (4-chloro-3-isobutyl-2-methoxyquinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (848 mg, 2.21 mmol, Intermediate 66: step d) in 3 mL THF was introduced at -45 C. After 10 minutes, the reaction vessel was placed in an ice-water bath. The reaction mixture was quenched after 40 minutes with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (4*30 mL) and EtOAc:THF (1:1, 30 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (100% DCM increasing to 5% MeOH-DCM) provided the title compound as an off white amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.07 (d, J=2.2 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.32 (dd, J=8.7, 2.2 Hz, 1H), 6.99-6.88 (m, 3H), 4.24 (s, 1H), 4.09 (s, 3H), 3.92 (s, 3H), 2.80 (d, J=7.3 Hz, 2H), 2.53 (s, 3H), 2.36 (s, 3H), 2.08 (hept, J=6.8 Hz, 1H), 0.95 (dd, J=6.7, 1.5 Hz, 6H). MS (ESI): mass calcd. for C25H28ClN5O2, 465.2. m/z found 466.0 [M+H]+. The racemate was separated by chiral chromatography using: Chiralpack OD-H column, 80% heptane/20% ethanol, to give Example 133b as the first compound eluted from the chiral column and Example 133c as the second compound eluted from the chiral column.

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

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7343-33-1 name is 5-Bromo-1H-1,2,4-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. 7343-33-1

A dry round bottom flask was charged with 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100¡ã C. for 36 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered through a plug of Celite? and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash chromatography (silica/EtOAc/Hexanes) yielded 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole as an off white solid (3.78 g, 73percent yield): mp 67-69¡ã C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta -58.02.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1H-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; Dow AgroSciences LLC; DENT, III, William Hunter; GIAMPIETRO, Natalie C.; US2014/275564; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, 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 16681-65-5. 16681-65-5

A 2.5 M solution of n-butyllithium in hexanes (9.60 mL, 24.0 mmol) was added dropwise to a stirring solution of 1-methyl-1H-1,2,3-triazole (2.00 g, 24.0 mmol, prepared according to PCT Int. Appl., 2008098104) in dry THF (100 mL) at -50 C. The reaction became heterogeneous and yellow during addition. After 15 minutes, a solution of tert-butyl 3-formylazetidine-1-carboxylate (4.45 g, 24.0 mmol) in dry THF (10 mL) was added dropwise by syringe. The reaction mixture became homogeneous and was allowed to slowly warm to 0 C. Water (10 mL) and ethyl acetate (100) mL were added. The biphasic mixture was warmed to 23 C. The mixture was partitioned between half-saturated aqueous sodium chloride solution (100 mL) and ethyl acetate (300 mL). The layers were separated. The organic layer was dried with sodium sulfate and the dried solution was filtered. Celite (14 g) was added to the filtrate and the solvents were removed by rotary evaporation to provide a free-flowing powder. The powder was loaded onto a silica gel column. Elution with ethyl acetate initially, grading to 5% methanol-ethyl acetate provided the title compound as a white foam.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Methyl-1H-1,2,3-triazole.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-34-2, 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. 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, A new synthetic method of this compound is introduced below.

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 ¡ãC 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).

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; 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

288-36-8, 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 288-36-8 as follows.

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 4 nights. The reaction was diluted with water, washed with ether, and acidified with cone. HC1. The acidic aqueous solution was extracted 3x with ethyl acetate 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 ethyl acetate) in hexanes], providing the title compound as an off-white solid. LRMS m/z (M+H) 196.2 found, 196.1 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 288-36-8, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/95442; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, 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. 4928-87-4 name is 1,2,4-Triazole-3-carboxylic acid, 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.

Intermediate W (75 mg, 0.15 mmol) was dissolved in NMP (841 muL) before HATU (75 mg, 0.20 mmol), 1H-1,2,4-triazole-3-carboxylic acid (21 mg, 0.18 mmol) and N-ethyl-N-isopropyl-propan-2-amine (105 muL, 0.60 mmol) were added. The solution was stirred at room temperature for 1h before aq. NH4Cl was added and the aq. phase was extracted twice with EtOAc. The combined organic phase was washed with sat.aq. NaHCO3 and brine, dried over MgSO4, filtered and the filtrate evaporated under reduced pressure. The residue was purified flash chromatography on silica gel eluting with 0-100% EtOAc: Hexanes affording the title compound. (7-(tert-Butyl)-5-(4-fluoro-3- methylphenyl)furo[3,2-b]pyridin-2-yl)(2,2-dimethyl-4-(1H-1,2,4-triazole-3- carbonyl)piperazin-1-yl)methanone (17 mg, 21% yield). 1H NMR (400 MHz, DMSO-d6) 8.68 (s, 1H), 8.07 – 7.99 (m, 1H), 7.94 (ddd, J = 8.0, 5.2, 2.4 Hz, 1H), 7.71 (d, J = 8.5 Hz, 1H), 7.48 (d, J = 9.8 Hz, 1H), 7.22 (td, J = 9.1, 3.7 Hz, 1H), 4.48 (s, 1H), 4.10 – 3.61 (m, 6H), 2.31 (t, J = 2.5 Hz, 3H), 1.61 – 1.39 (m, 15H). Signals doubled due to amide rotamers. ESI-MS m/z calc.518.2442, found 519.09 (M+1)+; Retention time: 3.30 minutes using method A

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; VERTEX PHARMACEUTICALS INCORPORATED; SAYEGH, Camil Elie; STURINO, Claudio; FOURNIER, Pierre-Andre; LACOSTE, Jean-Eric; DIETRICH, Evelyne; MARTEL, Julien; VALLEE, Frederic; (494 pag.)WO2016/154075; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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. 288-36-8.

To a 20 ml microwave vial containing 2-bromo-4,5-dimethoxybenzoic acid (3 g, 1 1 .5 mmol), copper iodide (0.04 g, 0.5 mol%), cesium carbonate (7.5 g, 23 mmol), triazole (1 .33 mL, 23 mmol) and finally (R,R)-(-)-N,N’-dimethyl-1 ,2- cyclohexanediamine ligand (0.36 mL, 2.3 mmol) was added DMF (12 mL). The resulting clumpy yellow slurry was stirred until evenly dispersed then heated to 120C for 10-20 min using a microwave. At this point the reaction mixture appeared as a blue slurry which was then diluted with 20 mL ether and 20 mL H2O. The resulting solution was thoroughly stirred and transferred to a seperatory funnel then the RBF was subsequently rinsed with 20 mL ether and H2O each. The aqueous layer was separated from the organic layer and acidified to pH 1 with 6 mL cone. HCI. The now brown/ lime green aqueous layer was extracted twice with EtOAc. The bright yellow organic layers were combined and dried with Na2SO4 and then cone, into a yellow powder under reduced pressure which was purified by FCC (0-5% MeOH in DCM w/ 0.5% AcOH) to afford 2,3-dimethoxy-6-[1 ,2,3]triazol-2-yl-benzoic acid (60%) and 2,3- dimethoxy-6-[1 ,2,3]triazol-1 -yl-benzoic acid (20%). Data for 2,3-dimethoxy-6- [1 ,2,3]triazol-2-yl-benzoic acid, MS (ESI): mass calculated for CnHnN3O4, 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.87 (s, 2H), 7.47 (s, 1 H), 7.18 (s, 1 H), 3.94 (s, 3H), 3.91 (s, 3H).; Intermediate 80: 2,3-Dimethoxy-6-[1 , 2, 3]triazol-1 -yl-benzoic acid.The title compound was isolated from the procedure used to prepareIntermediate 79 with a 20% yield. MS (ESI): mass calculated for Cn Hn N3O , 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.17 (d, J = 1 .0 Hz, 1 H), 7.82 (d, J = 1 .0 Hz, 1 H), 7.62 (s, 1 H), 7.09 (s, 1 H), 3.95 (s, 3H), 3.91 (s, 3H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics