Category: Triazoles

These common heterocyclic compound, 6086-21-1, name is 1-Methyl-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. 6086-21-1

Example 133.; Preparation of 8-(1-ethyl-propyl)-3-[3-methoxy-5-(2-methyl-2H-[1,2,4]triazol-3-yl)- thiophen-2-yl]-2,6-dimethyl-imidazo[1,2-b]pyridazine.; A. 5-Bromo-1-methyl-1H-[1,2,4]triazole.; EPO To a -78 C solution of l-methyl-1H-[1,2,4]triazole (1.0 mL, 13.20 mmol) and TEtaF (100 mL) is added 1.6 M n-BuLi (8.70 mL, 13.86 mmol). After 45 minutes 1,2- dibromo-l,1,2,2-tetrafluoro-ethane (1.76 mL, 14.52 mmol) is added, the solution is warmed to ambient temperature and stirred for 2 hours. The solution is diluted with EtOAc (200 mL), washed with water (150 mL), brine (150 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (1.37 g, 8.46 mmol, 64%). 1H NMR (CDCl3) delta 3.82 (s, 3H), 7.78 (s, 1H). LC/MS (m/z): calcd. for C3H4BrN3 (M+H)+: 162.0; found: 161.9.

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 6086-21-1.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/102194; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, 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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below.

Intermediate H 4-Fluoro-2-(2H-l,2,3-triazol-2-yl)benzoic acid Intermediate H To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol), cesium carbonate (89.26 g, 274 mmol) and Cul (5.27 g, 27.4 mmol) in DMF (200 mL) were added NN’- dimethylcyclohexane-l,2-diamine (3.7 mL,23.3 mmol) and lH-l,2,3-triazole (18.92 g, 274 mmol). The resulting mixture was stirred at 110 C overnight, cooled, concentrated in vacuo and diluted with water (150 mL). The aqueous mixture was extracted with EtOAc (300 mL x 3). The aqueous layer was acidified with 2Nu HC1 and extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine (150 mL x 3), dried over Na2SC>4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether : EtOAc = 100: 1 ~ 5 : 1) to provide the title compound. LRMS m/z (M+H) 208.0 found, 208.0 required.

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.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (116 pag.)WO2016/100161; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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. 7411-23-6

NaH (60% dispersion in mineral oil; 5.29 g, 132 mmol) was added to a stirred solution of 3,5-dibromotriazole (20.0 g, 88.2 mmol) in DMF under an atmosphere of N2 at r.t. After 30 min, 2-iodopropane (10.6 ml, 106 mmol) was slowly added and the r.m. was heated at 40 C. for 2-3 h. The content was carefully poured onto ice/H2O (1 l), and the mixture was extracted with DIPE. The combined organic extracts were washed with H2O (4¡Á200 ml), then with brine and dried (Na2SO4). Filtration and concentration under reduced pressure yielded a yellow oil. Yield: 16.50 g of intermediate 24 (70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7411-23-6, its application will become more common.

Reference:
Patent; Van Brandt, Sven Franciscus Anna; De Cleyn, Michel Anna Jozef; Gijsen, Henricus Jacobus Maria; Berthelot, Didier Jean-Claude; Surkyn, Michel; US2012/295891; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, Adding a certain compound to certain chemical reactions, such as: 288-36-8, name is 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 288-36-8.

lH-Triazole (760 mg, 11 mmol) was added to a suspension of 2,3-dichloro-5-nitro-pyridine (965 mg, 5 mmol) and anhydrous potassium carbonate (1.03 g, 7.5 mmol) in THF (50 mL), and the mixture was stirred overnight at room temperature. The mixture was diluted with EtOAc (100 mL), washed with water and brine, and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica chromatography (hexane: EtOAc= 5: 1 to 1: 1) to give the title compound (505 mg, 44%). 1H NMR (400 MHz, DMSO-iM): delta 9.39 (d, 1H), 9.15 (d, 1H), 8.34 (s, 2H).

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; CORNELL UNIVERSITY; DANA-FARBER CANCER INSTITUTE, INC.; CHILDREN’S MEDICAL CENTER CORPORATION; MELNICK, Ari, M.; GABAS, Lorena, Fontan; US, Ilkay; CASALENA, Gabriella; GRAY, Nathanael, S.; SCOTT, David, A.; HATCHER, John; DU, Guangyan; WU, Hao; QIAO, Qi; (157 pag.)WO2018/85247; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-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. 7411-23-6

To a stirred solution of N,N-diisopropylethylamine (5.7 mL, 33.0 mmol), bromotripyrrolidinophosphonium hexafluorophosphate (5.14 g, 11.02 mmol) and pyridine oxide (1.05 g, 11.0 mmol) in DCM (25 mL) at r.t under nitrogen was added 3,5-dibromo-1H-1,2,4-triazole (0.08 mL, 11.02 mmol) in a single portion and the reaction stirred at 25 C overnight. The solvents were removed in-vacuo and the residue partitioned between 50 mL of DCM and 35 mL of water, passed through a phase separation cartridge and concentrated in-vacuo. The crude material was purified by column chromatography (SiO2) eluting with 10-60% EtOAc in Pet. Ether to give 2-(3,5-dibromo-1,2,4-triazol-1-yl)pyridine (1.95 g, 6.4 mmol, 58 % yield) as a white crystalline solid. Intermediate 8: UPLC-MS (ES+, Method A): 1.53 min, m/z 304.9 [M+H]+.1H NMR (400 MHz, DMSO-d6) delta 8.66 (ddd, J = 4.7, 1.9, 0.8 Hz, 1H), 8.15 (td, J = 7.8, 1.9 Hz, 1H), 7.82 (dt, J = 8.1, 1.0 Hz, 1H), 7.66 (ddd, J = 7.5, 4.9, 1.0 Hz, 1H). Structure confirmed by DEPT NMR. A second compound was isolated to give 4-(3,5-dibromo-1,2,4-triazol-1-yl)pyridine (120 mg, 0.40 mmol, 3.6% yield). Intermediate 9: UPLC-MS (ES+, Method A): 1.33 min, m/z 304.9 [M+H]+.1H NMR (400 MHz, DMSO-d6) delta 8.93-8.80 (m, 2H), 7.82-7.74 (m, 2H). Structure confirmed by DEPT NMR

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 7411-23-6.

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

These common heterocyclic compound, 930-33-6, name is 1H-1,2,4-Triazol-3(2H)-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. 930-33-6

509 g (28.28 mol) of water are added to a solution of the obtained OTA (in 98% sulfuric acid) with stirring and then 213 g (3.38 mol) of concentrated nitric acid (98% by weight commercial nitric acid) are added.After the introduction of nitric acid, the medium was brought to 65 DEG C and stirred at this temperature for 2 hoursSamples are taken to monitor the progress of the nitration (when the temperature of the reaction medium reaches 65 ). The sample is analyzed after external calibration (using commercial ONTA). The results are shown in Fig. Can be obtained at a very high yield.The following procedure was carried out for the recovery of the prepared ONTA.The reaction medium is cooled to 10 C (at the expiry of 2 hours). Subsequently, an amount of 293 g (16.28 mol) of water is added while maintaining the temperature at 10 . The crystallized ONTA is then filtered off and then pull-dried on a Buchner filter.The weight of the recovered wetted ONTA is 403 g.HPLC analysis (of the recovered ONTA) shows that after external calibration (by commercial ONTA), a yield of 96% of the wet product (for the starting ATA) can be achieved.

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 930-33-6.

Reference:
Patent; Hercules; Yurenko; Herve, Gregoire; Jacob, Gi; Kanyong, Gi; Busay, Jang Marque; (13 pag.)KR2016/28405; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-88-0, name is 1H-1,2,4-Triazole, molecular formula is C2H3N3, 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. 288-88-0

EXAMPLE 108 1-phenyltriazole 1 g (0.0145 mol) triazole 2, 0.21 g (0.00145 mol) copper(I)oxide, 0.29 g (0.00145 mol) phenantroline monohydrate and 6.01 g (0.044 mol) potassium carbonate are weighed into a Schlenk flask. After repeated evacuating and flushing with argon, 10 ml dry DMF is added. Evacuating and flushing with argon are repeated several times. Subsequently, 2.42 ml (4.43 g, 0.022 mol) of iodobenzene is added. The reaction mixture is stirred for 48 h at 100 C. under argon. After cooling 20 ml DCM is added and filtered. The solvent is removed in vacuum and the product is obtained after purification by column chromatography (KG 60, gradient petroleum ether/EtOAc 8:2 to EtOAc) as a yellowish-white solid.M 145.17 C8H7N3 Yield: 1.362 g (65%)1H-NMR DM-94 (300 MHz/DMSO): (ppm)=7.41 (t, 1H, 6-H); 7.58 (t, 2H, 5/5′-H); 7.87 (d, 2H, 4-H); 8.25 (s, 1H, 1-H); 9.31 (s, 1H, 2-H)13C-NMR DM-94 (75.475 MHz/DMSO): (ppm)=119.37 (5/5′-C); 127.78 (6-C); 129.77 (4/4′-C); 136.74 (3-C); 142.27 (2-C); 152.39 (1-C)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-88-0, its application will become more common.

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

6523-49-5,Some common heterocyclic compound, 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, molecular formula is C8H8N4, 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 formamidine from Step 1 (151 mg) and 4-triazolylaniline(100 mg) in AcOH (5 ml) were heated to 125 for 3 h. The cooled reaction mixture was basified with 2N NaOH and the precipitate isolated by filtration and purified by column chromatography on silica gel with DCM:MeOH (2.5%) as eluant. This gave the title compound (200 mg).1H NMR delta 10.1 (IH, s), 9.3 (IH, s), 8.83 (IH, s), 8.63 (IH, s), 8.26 (IH, s), 8.19 (IH, d, J 8.85Hz), 8.07 (2H, d, J 8.85Hz), 7.92 (2H, d, J 8.85Hz), 7.85 (IH, d, J8.85Hz), 7.76 (IH, d, J 2.5Hz), 7.70 (IH, d, J 5Hz), 7.27 (IH, m); LC-MS rt 2.39 m/z369 ES-.

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)aniline, its application will become more common.

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

A common compound: 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 4928-87-4

5-(3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9- dihydropyrazolotl,5-a]pyrido[3?2-e]pyrimidin-6(7H)-one (49.78 mg, 0.44 mmol) in DMF (2 mL) was treated with EDCI (129.47 mg, 0.678 mmol) and HOBt (45.6 mg, 0.339 mmol). Then substrate 5-(3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9~dihydropyrazolo[l,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one (122 mg, 0.21 rnmol) followed by DIEA (0.29 mL, 1.69 mmol) was added. After 30 min, the reaction mixture was treated with water (0.4 mL) and DMSO-MeCN (3:1, 3 mL). Pure compound 5-((lR,5S)-9-(lH- 1,2,4- triazole-3-carbonyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-3-(6-phenylpyridin-3-yl)-8,9- dihydropyrazolo[l,5-a]pyrido[352-e]pyrimidin-6(7H)-one was isolated by preparative HPLC. HPLC-MS 4.35 min (UV 254 r.m). Mass calculated for formula C30H27N9O3 561.2; observed MH+ (LCMS) 561.98 (m/z).

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, 4928-87-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; MENG, Zhaoyang; REDDY, Panduranga Adulla, P.; SIDDIQUI, M. Arshad; MANDAL, Amit, K.; LIU, Duan; ZHAO, Lianyun; MCRINER, Andrew; WO2012/27234; (2012); 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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, A new synthetic method of this compound is introduced below., 41253-21-8

EXAMPLE 2; Preparation of 1,3-benezenediacetonitrile, alpha,alpha,alpha’,alpha’-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl) (Formula I) 2 Kg of 2-[3-bromomethyl-5-cyano-dimethyl-methyl)-phenyl]-2-methyl-propionitrile and 10 L of N,N-dimethylacetamide were charged in a clean dry reactor followed by stirring for 10 minutes. 0.861 Kg of sodium triazole was charged under nitrogen pressure and the temperature raised to 57.5 C. The obtained solution was maintained for 36 hours at 57.5 C. and then cooled to about 25 C. followed by quenching the reaction by charging the solution to 30 L of water. The resultant reaction solution was extracted with 3¡Á20 L of ethyl acetate followed by separation of organic and aqueous layers. The combined organic layer was distilled at 26.2 C. under a vacuum of -0.6 Kg/cm2 to afford a residue, the and the obtained residue was dissolved in 20 L of toluene followed by treatment with 2¡Á2 L of 2N aqueous hydrochloric acid solution and with 2¡Á8 L of water. The aqueous layer was separated and treated with 4¡Á10 L of toluene and the obtained aqueous layer was charged into sodium bicarbonate solution, which was prepared by the dissolution of 4.7 Kg of sodium bicarbonate in 45 L of water. The obtained solution was stirred for 10 minutes and then extracted with 2¡Á20 L of dichloromethane. A silica gel bed in a stainless steel column filter (2.05 cm diameter and 5.75 cm height) was prepared with 6.4 Kg of 230-400 mesh silica gel and the bed was washed with 4 L of ethyl acetate. The dichloromethane solution from above was passed through the silica gel bed and then the bed was washed with 38 L of ethyl acetate. The combined solution and washing was concentrated at 24.7 C. under a vacuum of -0.6 Kg/cm2 and cooled to 30 C. followed by dissolution of the residue in 1.4 L of isopropyl alcohol. The obtained solution was stirred for 10 minutes at 30 C. and 7 L of water were charged. The obtained suspension was stirred for 3 hours followed by filtration through a Nutsche filter and washing the obtained solid with a solution of 0.25 L of isopropyl alcohol and 1 L of water. The resultant solid was dried at 48 C. under vacuum of 690 mm Hg for 3 hours to afford 0.470 Kg of the title compound having a water content by Karl Fischer of 0.13% w/w.

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; Murki, Veerender; Palle, Venkata Raghavendra Acharyulu; Panchbhai, Pandurang Prasad; US2007/100148; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics