Day: April 8, 2021

These common heterocyclic compound, 40253-47-2, name is Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate, 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. Application In Synthesis of Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate

To a solution of ethyl 5-methyl-lH-l,2,4-triazole-3-carboxylate (1.0 g, 6.44 mmol) and l-bromo-3-(bromomethyl)benzene (1.77 g, 7.08 mmol) in THF (32 mL), K2CO3 (1.78 g, 12.88 mmol) was added. The mixture was stirred at 50¡ãC for 18 h, and then the reaction was filtered under vacuum. The solvent was removed under reduced pressure and the crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12percent to 100percent EtOAc) to afford ethyl l-(3- bromobenzyl)-5-methyl-lH-l,2,4-triazole-3-carboxylate (1.25 g, 60percent) as a viscous oil. MS(ES+) Ci3H14BrN302 requires: 323, 325 found: 324, 326 [M+H]+(l :l).

The synthetic route of Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; CARROLL, Christopher, L.; MARSZALEK, Joe; CZAKO, Barbara; JOHNSON, Ryan; THEROFF, Jay; WO2014/31936; (2014); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 288-36-8, name is 1H-1,2,3-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. Recommanded Product: 288-36-8

Into a 3000-mL 3-necked round-bottom flask, was placed 2H-1,2,3-triazole (100 g, 1.45 mol, 1.00 equiv), water (1000 mL), Br2 (522 g, 3.27 mol, 2.25 equiv). The resulting solution was stirred overnight at 50 C. in an oil bath. The reaction was then quenched by the addition of 1000 mL of Na2SO3 (aq). The solid was collected by filtration and dried in an oven under reduced pressure. This resulted in 313 g (95%) of 4,5-dibromo-2H-1,2,3-triazole as a white solid.

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

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 288-36-8, These common heterocyclic compound, 288-36-8, name is 1H-1,2,3-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.

To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol), cesium carbonate (89.26 g, 274 mmol) and CuI (5.27 g, 27.4 mmol) in DMF (200 mL) were added N,N?-dimethylcyclohexane-1,2-diamine (3.7 mL,23.3 mmol) and 1H-1,2,3-triazole (18.92 g, 274 mmol). The resulting mixture was stirred at 110 oC overnight, cooled, concentrated in vacuo and diluted with water (150 mL). The aqueous layer was extracted with EtOAc (300 mL x 3). The aqueous layer was acidified with 2N HCl and extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine (150 mL x 3), dried over Na2SO4, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether : EtOAc = 100: 1 ~ 5 : 1) to provide the title compound as a solid. LRMS m/z (M+H) 208.0 found, 208.0 required.

Statistics shows that 1H-1,2,3-Triazole is playing an increasingly important role. we look forward to future research findings about 288-36-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; LUO, Yunfu; (68 pag.)WO2016/89721; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 129027-65-2, name is 1-(tert-Butyl)-1H-1,2,3-triazole-4-carbaldehyde belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Safety of 1-(tert-Butyl)-1H-1,2,3-triazole-4-carbaldehyde

Synthesis of N,N-bis((1-tert-butyl-1H-1,2,3-triazol-4-yl)methyl)prop-2-yn-1-amine To a 250-mL round bottom flask was added a solution of 1-tert-butyl-1H-1,2,3-triazole-4-carbaldehyde (2.47 g, 16.1 mmol, 2.2 eq) in 84 mL dichloroethane (?0.2 M), followed by addition of propargyl amine (361 mg, 7.2 mmol, 1.0 eq). To this mixture sodium triacetoxyborohydride (3.8 g, 17.9 mmol, 2.5 eq) was added in one portion with vigorous stirring. The reaction mixture was stirred at rt for 40 h. 1N H2SO4 (86 mL) was added to the reaction, and the mixture was stirred for 15 min. The pH was adjusted to >10 by addition of potassium carbonate. The reaction mixture was diluted with 100 mL of water and extracted with dichloromethane (3*300 mL). The organic layers were combined, dried over anhydrous MgSO4, filtered, and concd in vacuo to provide a crude product.Further purification by flash chromatography (100 g silica gel, 20% hexanes in EtOAc, Rf 0.2, KMnO4 stain) provided 1.98 g of product (yield: 84%) as a white powder. mp 125.5-126.1 C.; 1H NMR (300 MHz, CDCl3) delta 7.67 (s, 2H), 3.87 (s, 4H), 3.40 (d, J=2.4 Hz, 2H), 2.28 (t, J=2.4 Hz, 1H), 1.67 (s, 18H); 13C NMR (75 MHz, CDCl3) delta 143.6, 120.2, 78.8, 73.5, 59.2, 47.8, 42.2, 30.0; HRMS cacld for [M+H]+ C17H28N7 330.2406, found 330.2400.

The synthetic route of 129027-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Albert Einstein College of Medicine of Yeshiva Uni; Wu, Peng; Soriano del Amo, David; Wang, Wei; Marlow, Florence L.; US2013/295019; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4928-88-5, 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. 4928-88-5 name is Methyl 1H-1,2,4-triazole-3-carboxylate, 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.

EXAMPLE 1 1-(d,l-Tetrahydropyran-2-yl)-1,2,4-triazole-3-carboxamide A mixture of methyl 1,2,4-triazole-3-carboxylate (12.7 g, 0.10 mole), 2,3-dihydropyran (16 ml), bis(p-nitrophenyl) phosphate (0.10 g) and anhydrous dimethylformamide (100 ml) was heated at 75¡ã-80¡ã for 3 hrs. Additional 2,3-dihydropyran (8 ml) was added and heating at 75¡ã-80¡ã was continued for 3 hrs. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (150 ml). The ethyl acetate solution was washed with aqueous sodium hydrogen carbonate (two 25 ml portions) and water. The solution was dried over magnesium sulfate, filtered and the filtrate was evaporated to dryness. The crude product, methyl 1-(d,l-tetrahydropyran-2-yl)-1,2,4-triazole-3-carboxylate, was treated for 20 hrs at 25¡ã with methanol saturated with anhydrous ammonia. The solvent was removed in vacuo and the product was crystallized from ethanol to provide 14.0 g (71percent). Recrystallization from ethanol afforded 11.7 g (60percent) of pure 1-(d,l-tetrahydropyran-2 -yl)-1,2,4-triazole-3-carboxamide with mp 156¡ã-158¡ã. NMR (DMSO-d6) delta 8.82 (S, 1, H-5). Anal. Calcd for C8 H12 N4 O2: C, 48.97; H, 6.17; N, 28.56. Found: C, 48.95; H, 6.22; N, 28.42.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1H-1,2,4-triazole-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ICN Pharmaceuticals, Inc.; US3991078; (1976); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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. Formula: C3H3N3O2

[0688] Compound 3 (7 .0 mg, 16 f.tmol) was combined withDMF (0.5 mL), 1H-1,2,3-triazole-5-carboxylic acid (2.0 mg,18 f.tmol), HATU (6.8 mg, 18 f.tmol) and DIPEA (8.5 f.LL, 49f.tmol). The mixture was stirred for 30 minutes after whichtime LCMS showed the desired product formation, Compound4, which was used directly in the next step.

The synthetic route of 1H-[1,2,3]Triazole-4-carboxylic acid 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.; US2015/210690; (2015); 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 1533519-84-4 as follows. Application In Synthesis of 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Example 10. Preparation of phenyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate [075] To a round bottom flask added 4-(4-cyclopropyl-l-yl)-4H-l,2,4-triazole-3-thiophenol (40.0 g), acetone (600 mL) and triethylamine (16.6 g) to form a mixture at room temperature, after stirred for 20 min, the mixture was cooled to 0C, then was added drop wise a solution of phenyl chloroacetate in isopropanol (33.8 g of phenyl chloroacetate was dissolved in 200 mL of acetone), during the addiction the mixture was maintained at about 0C, after the addition, the mixture was warm to 20C, after stirred for about 2 hours, the reaction was complete, filtered, and the filter cake was washed with acetone (100 mL), after filtration, the filter cake was added purified water (700 mL) to give a slurry, the slurry was stirred for 1 hour, then the purified water was removed by vacuum filtration, the filter cake was dried in vacuum at about 50C for about 24 hours to obtain phenyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate, yield 90% the HPLC purity(area) 99.2%.

According to the analysis of related databases, 1533519-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHEN, Weiqiang; LUO, Jian; LIU, Lixue; FAN, Yuping; WO2014/198241; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

1455-77-2, name is 3,5-Diamino-1,2,4-triazole, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C2H5N5

Example 243: Preparation of 6-((4-((3-amino-lH-l,2,4-triazol-5-yl)amino)-5-(trifluoro methyl)pyrimidin-2-yI)amino)-3,4-dihydroquinolin-2(lH)-one6-((4-Chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3,4-dihydroquinolin-2(lH)-one (0.072 g, 0.210 mmol), lH-l ,2,4-triazole-3,5-diamine (0.021 g, 0.210 mmol) and -ethyl-N- isopropylpropan-2-amine (0.037 ml, 0.210 mmol) were mixed in DMF (2 ml). The mixture was microwaved at 1 10 ¡ãC for 20 min. Added copper (6.68 mg, 0.105 mmol) and more base and the mixture was microwaved at 130 ¡ãC for 20 min and then concentrated. 7 mg of product was recovered after automated reverse phase chromatography (water-3percent DMF in MeCN eluent). MS calcd for [C16Hi4F3N90+H]+: 406.14, found 406.10.

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, 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 27996-86-7, COA of Formula: C9H7N3O

Example 94 Preparation of 1-(4-Vinylphenyl)-1H-1,2,4-triazole (DI59) To a stirred solution of 4-[1,2,4]-triazol-1-yl-benzaldehyde (9.0 g, 52 mmol) in 1,4-dioxane (100 mL), were added K2CO3 (10.76 g, 78 mmol) and methyl triphenyl phosphonium bromide (22.2 g, 62.4 mmol) at ambient temperature. The resultant reaction mixture was heated to 70 C. for 18 h. After completion of the reaction (TLC), the reaction mixture was cooled to ambient temperature and filtered and the obtained filtrate was concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether) to afforded the title compound as a white solid (5.6 g, 63%): ESIMS m/z 172.09 ([M+H]+).

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, 4-[1,2,4]Triazol-1-yl-benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-36-8, 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. 288-36-8 name is 1H-1,2,3-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.

A solution of2-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 sparged with nitrogen and heated to 75 oc for 96h. The cooled reaction mixture was diluted with water, washed with ether, and acidified withcone. HCl. The acidic aqueous solution was extracted 3x with EtOAc and the combined organic fractions washed with brine, dried over MgS04, filtered, and concentrated in vacuo. The crudematerial was purified by silica gel chromatography [0-70% (1% acetic acid in EtOAc) inhexanes], to provide 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, 1H-1,2,3-Triazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/18029; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics