Triazoles

Reference of 7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

Procedure: A 500 mL round bottom flask was loaded with 4-methoxy-7-chloro-6-azaindole 2e (9.1 g, 50 mmol; dried in vacuo), potassium carbonate (13.8 g, 100 mmol, 2 eq.), copper powder (6.35 g, 100 mmol, 2 eq.), and 3-methyl-1,2,4-triazole (83 g, 1.0 mol, 20 eq.). The solid mixture was heated to melt at 170-175 C. (external oil bath temperature) under a gentle stream of anhydrous nitrogen for 12 h, by which time HPLC analysis indicated that the amount of the peak for the starting material had become 5-30% and the desired product peak becomes about 45% with isomeric by-product peak becomes 15%. As the reaction mixture cooled, MeOH (150 mL) was added slowly to the warm, stirred mixture. Upon cooling, the insoluble material (copper powder) was filtered through a Celite pad, and rinsed with methanol. The filtrate was concentrated in vacuo to a thick paste which was diluted with water (1 L) and extracted with EtOAc (3¡Á150 mL). The EtOAc extracts were dried (MgSO4), filtered and concentrated to obtain about 8 g of crude residue which was crystallized by dissolving in hot CH3CN (50 mL), followed by diluting with water (100 mL) and cooling at 0 C. to collect 1.45 g (12.7%) of the title compound as white solid. The filtrate was purified by C-18 reverse phase silica gel (YMC ODS-A 75 mum) eluted with 15-30% CH3CN/H2O. Appropriate fractions were combined and the aqueous solution after removing CH3CN by rotary evaporator was lyophilized to give additional 1.15 g of the title compound 3-81. The crude aqueous layer was further extracted with EtOAc several times. The ethyl acetate extracts were dried (MgSO4), filtered, concentrated, and crystallized from MeOH to give additional 200 mg of the title compound 3-81. The total yield: 2.8 g (12.2 mmol, Y. 24.5%); MS m/z 230 (MH), HRMS (ESI) m/z calcd for C11H12N5O (M+H), 230.1042, found 230.1038 (Delta-1.7 ppm); 1H NMR (CDCl3) delta ppm 2.54 (3H, s, CH3), 4.05 (3H, s, OCH3), 6.73 (1H, s, H-3), 7.40 (1H, s, H-2), 7.56 (1H, s, H-5), 9.15 (1H, s, triazole-H-5); 13C NMR (CDCl3, 125.7 MHz) 8 ppm 14.2 (triazole-Me), 56.3 (OMe), 100.5 (C-3), 116.9 (C-5), 123.5, 127.2, 127.5 (C-2), 129.5 (C-7), 141.2 (C-5′), 149.5 (C-4), 161.8 (C-3′); Anal. Calcd for C11H11N5O: C 57.63; H 4.83; N 30.55, found C, 57.37, H, 4.64, N, 30.68. The structure was confirmed by a single X-ray crystallographic analysis using crystals obtained from C-18 column fractions. A portion of C-18 column fractions containing a mixture of the desired 3-methyl-1,2,4-triazolyl analog 3-81 and isomeric 5-methyl-1,2,4-triazolyl analog 4-81 was further purified by C-18 reverse phase column eluting with 8-10% CH3CN/H2O. Appropriate fractions were extracted with CH2Cl2, and slow evaporation of the solvent gave crystalline material of the isomeric 7-(5-methyl-1,2,4-triazolyl)-4-methoxy-6-azaindole (4-81): MS m/z 230 (MH), 1H NMR (CDCl3) delta ppm 3.05 (3H, s, CH3), 4.07 (3H, s, OCH3), 6.74 (1H, q, J=2.4, H-2), 7.37 (1H, t, J=2.4, H-3), 7.65 (1H, s, H-5), 8.07 (1H, s, triazole-H-3). The structure was confirmed by a single X-ray crystallographic analysis.

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

Reference:
Patent; Ueda, Yasutsugu; Connolly, Timothy P.; Kadow, John F.; Meanwell, Nicholas A.; Wang, Tao; Chen, Chung-Pin H.; Yeung, Kap-Sun; Zhang, Zhongxing; Leahy, David Kenneth; Pack, Shawn K.; Soundararajan, Nachimuthu; Sirard, Pierre; Levesque, Kathia; Thoraval, Dominique; US2005/209246; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16681-65-5, name is 1-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. Application In Synthesis of 1-Methyl-1H-1,2,3-triazole

A solution of n-butyllithium in hexanes (2.5 M, 22.5 mL, 56.3 mmol) was added dropwise by syringe to a stirring solution of 1-methyl-1H-1,2,3-triazole (5.00 g, 60.2 mmol, prepared according to PCT Int. Appl., 2008098104) in dry tetrahydrofuran (400 mL) at -55 C. The resulting off-white slurry was stirred at -45 C. for 20 min, whereupon a solution of 2,6-dimethyl-pyridine-3-carbaldehyde (8.33 g, 61.7 mmol) in dry tetrahydrofuran (10 mL) was added dropwise by syringe. After 5 min, the cooling bath was removed and the reaction mixture was allowed to slowly warm. After 45 min, saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (100 mL) were added. The whole was concentrated by rotary evaporation. The residue was dissolved in ethyl acetate (300 mL). The organic solution was washed with saturated aqueous sodium chloride solution (100 mL, containing excess solid sodium chloride). The aqueous layer was extracted with ethyl acetate (2*100 mL). The organic layers were combined and the combined solution was concentrated. Ether (100 mL) was added to the residue and the mixture was sonicated for 20 min during which time a white solid crashed out. The solids were collected by filtration. Ether (100 mL) was added to the collected solids and the mixture sonicated a second time. After 20 min, the mixture was filtered and the solids were collected to provide the title compound as a fine powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-65-5, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; 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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

3H-l,2,3-triazole-5-carboxylic acid (2.5 mg, 22 muiotaetaomicron) was combined with HATU (8.4 mg, 22 muiotaetaomicron) in DMF (0.3 mL) and stirred for 10 minutes; Et3N (1 eq.) was added and the mixture was stirred for 1 minute. Compound 2 (22 muiotaetaomicron) was dissolved in DMF (0.5 mL) and Et3N (3.1 mu, 22 muiotaetaomicron) was added, followed by addition of the activated acid solution. The mixture was stirred for 30 minutes, concentrated, and purified by preparative HPLC to yield the title compound. MS m/z [M+H]+ calc’d for C27H31CIFN5O4, 544.21 ; found 544.2.

The chemical industry reduces the impact on the environment during synthesis 1H-[1,2,3]Triazole-4-carboxylic acid. I believe this compound will play a more active role in future production and life.

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

These common heterocyclic compound, 151899-62-6, name is 3-Iodo-1-trityl-1H-1,2,4-triazole, 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. HPLC of Formula: C21H16IN3

Nitrogen gas was bubbled through a solution of 3-iodo-1-trityl-1H-1,2,4-triazole (i-28, 37.3 g, 85.35 mmol) and triethylamine (17.8 ml, 128 mmol) in anhydrous DMF (300 ml) heated at 35 C. for 30 mins. Pd(PPh3)2Cl2 (2.4 g, 3.4 mmol) and CuI (651 mg, 3.4 mmol) were added followed by addition of ethynyltrimethylsilane (18 ml, 128 mmol) in anhydrous DMF (18 ml) over 15 hours via syringe pump. After complete addition the mixture was heated at 35 C. for a further 5 hours. The mixture was poured into water (700 ml) and extracted with EtOAc (3¡Á300 ml). Combined EtOAc layers were washed with water (2¡Á500 ml), sat. NaCl (250 ml), dried over Na2SO4, filtered and evaporated. The residue was purified by MPLC on silica gel eluting with a gradient from 100% hexanes to 10% EtOAc in hexanes to afford the title compound. 1HNMR (500 MHz, CDCl3) delta: 7.96 (s, 1H), 7.37 (m, 9H), 7.14 (m, 6H), 0.27 (s, 9H)

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

Reference:
Patent; Morriello, Gregori J.; DeVita, Robert J.; US2008/280836; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 3179-31-5, A common heterocyclic compound, 3179-31-5, name is 1H-1,2,4-Triazole-3-thiol, molecular formula is C2H3N3S, 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.

Step B–Cyclopentylmethyl 1,2,4-Triazol-3-yl Sulfide 1,2,4-Triazole-3-thiol (49.0 g; 0.484 mol) and 86% potassium hydroxide (32.0 g; 0.484 mol) were dissolved in methanol (500 ml) and refluxed for 1 h. The solution was then evaporated to dryness, and the residue redissolved in methanol (500 ml). Cyclopentylmethyl methanesulfonate (86.0 g; 0.484 mol) was added, the solution stirred under reflux for 8 h, and at room temperature overnight. The solution was evaporated and the residue dissolved in ether (500 ml) and water (1 1). The aqueous layer was separated and extracted with another portion of ether (500 ml). The ether solutions were combined, washed with saturated brine (500 ml), dried (MgSO4), filtered and evaporated, to afford cyclopentylmethyl 1,2,4-triazol-3-yl sulfide (85.0 g; 96%) as a waxy, white solid. NMR – d(CDCl3; 60 MHz) 1.0-2.4 (10H, m), 3.2 (2H, d, J=7 Hz), 8.1 (1H, s) and 13.4 (1H, br s).

The synthetic route of 3179-31-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US5308830; (1994); A;,
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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 288-36-8

To a mixture of the product from Step 2 (7.9 g, 38 mmol) , Cs2CO3 (24.8 g, 76 mmol) , and CuI (2.88 g, 7.6 mmol) in DMF (200 mL) was added 2H- [1, 2, 3] triazole (5.24 g, 76 mmol) and N,N’-dimethyl-cyclohexane-1, 2-diamine (0.9 g, 6.5 mmol) and the mixture was stirred at 110 overnight. The cooled mixture was adjusted topH 12 with 1 N sodium hydroxide and extracted with EtOAc (50 mL x 3) . The aqueous layer was adjusted topH 4 with 1 N HCl and extracted with EtOAc (50 mLx4) . The extracts were dried over Na2SO4, filtered, the filtrate concentrated in vacuo, and the residue was purified by silica gel column chromatography (petroleum ether: EtOAc10: 1) to provide the title compound. LRMS m/z (M+H) 196.0 found, 196.0 required.

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 288-36-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; (59 pag.)WO2016/101118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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 40253-47-2 as follows. Recommanded Product: Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate

A mixture of ethyl 5-methyl-lH-l ,2,4-triazole-3-carboxylate (1.0 g, 6.45 mmol) and sodium hydroxide (1.702 mL, 32.2 mmol) in tetrahydrofuran (30 mL) was stirred at ambient temperature for 16 hours. Volatiles were removed, and the residue was acidified with 1 N HQ solution. Water was removed under high vacuum, and the crude residue was purified by HPLC (0-70% acetonitrile in 0.1 % trifluoroacetic acid/water on Phenomenex C18 10 mupiiota (250 mm x 50 mm) column at a flowrate of 50 mL/minute) to give 460 mg of the title compound as a white solid.

According to the analysis of related databases, 40253-47-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 103755-58-4, A common heterocyclic compound, 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, molecular formula is C9H9N3O, 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.

Example 12: (R)-3-(l-Phenyl-cycloheptanecarbonyloxy)-l-(l-phenyl-lH- [1, 2,3]triazol-4-ylm ethyl)- l-azonia-bicyclo[2.2.2]octane chloridea) 4-Chloromethyl- 1 -phenyl- lH-[ 1 ,2,3]triazole (1 -Phenyl- IH-[1, 2, 3]triazol-4-yl)-methanol (700 mg) was treated with thionyl chloride (2 mL) in dichloromethane (10 mL). The mixture was stirred and heated under reflux to form a solution. The excess reagent and solvent were removed and the residue dissolved in dichloromethane (50 mL) and passed down a plug of silica gel. The silica was washed with dichloromethane followed by ether and the eluants combined and concentrated to afford the sub-titled compound as a crystalline solid (600 mg).1H NMR (399.826 MHz, CDCl3) delta 8.00 (s, IH), 7.73 – 7.68 (m, 2H), 7.54 – 7.48 (m, 2H), 7.47 – 7.41 (m, IH), 4.77 (s, 2H).

The synthetic route of 103755-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY Ltd.; FORD, Rhonan; WO2009/139709; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 13423-60-4, A common heterocyclic compound, 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, molecular formula is C8H7N3, 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.

EXAMPLE 113 1-phenyl-4-(hepr-1-yl)triazolium bromide 0.150 g (0.002 mol) 1-phenyltriazole 1 (actually, 0.3 g, there were still 2 eq. DMF contained in the educt) and 0.97 ml (1.110 g, 0.006 mol) 1-bromoheptane 2 are combined in a pressure tube. The reaction mixture was stirred 12 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, and dried in HV. M 324.26 C15H22N3Br Yield: 0.225 g (69%) 1H-NMR DM-170 (300 MHz/DMSO): delta (ppm)=0.87 (t, 3H, 13-H); 1.30 (m, 8H, 9/10/11/12H); 1.95 (qui, 21-1,8-H); 4.34 (t, 2H, 7-H); 7.68 (m, 3H, 5/5’/6H); 7.95 (d, 2H, 4/4′-H); 9.55 (s, 1H, 1-H); 11.10 (s, 1H, 2-H) 13C-NMR DM-170 (300 MHz/DMSO):

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

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 7343-34-2 as follows. category: Triazoles

In a 50 mL round-bottomed flask under N2 at 0 ¡ãC, sodium hydride (60percent in mineral oil, 0.184 g, 4.60 mmol) was added to a solution of 3,5-dimethyl-lH-l,2,4-triazole (0.311 g, 3.20 mmol) in DMF (12 mL) and the mixture was stirred for 20 min. 4-Bromobenzyl bromide (0.960 g, 3.84 mmol) was then added to the mixture and stirring was continued at RT for 2.5 h. The reaction mixture was then poured into H20 and the product was extracted with EtOAc (x3). The combined organic extract was washed with 0 (x3) and brine, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified on ISCO using a 40 g column (0-20percent MeOH-DCM) to afford the title compound (0.382 g, 1.44 mmol, 45percent yield) as an off-white solid. LC (Method B): 1.538 min. MS (APCI): calcd for C11H13BrN3 [M + H]+ m/z 266.0, found 266.1. 1H NMR (400 MHz, CDCI3) delta ppm 7.43 – 7.52 (m, 2H), 7.00 – 7.08 (m, J = 8.22 Hz, 2H), 5.16 (s, 2H), 2.37 (s, 3H), 2.35 (s, 3H).

According to the analysis of related databases, 7343-34-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics