Triazoles

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

Example 7 Part A To a solution of 1 (80 mg, 0.5 mmol) in DMF (5 mL) at 0 C., HOBt (135 mg, 1.0 mmol) was added, followed by EDCI (191 mg, 1.0 mmol). After stirring at 0 C. for 0.5 h, 4-[1,2,4]triazol-1-yl-phenylamine (80 mg, 0.5 mmol) was added. 4-Methoxy-2-methyl-phenylamine (70 mg, 0.5 mmol) was added 10 min later. The reaction was then warmed up to RT and was stirred at this temperature for overnight. Water was added and the formed precipitated was collected by filtration, which was purified using prep-HPLC to give the desired product (30 mg). LC-MS m/z 418.2 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1,2,4-Triazol-1-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US2007/43045; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, 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. Product Details of 956317-36-5

To a solution of the acid (10.4 g, 51.2 mmol) in THF (250 mL), CDI (8.7 g, 53.7 mmol) was added. After 3.5 h, aqueous NH3 solution (174.1 g, 25% in water, 2.56 mol) was added. The biphasic mixture was stirred at room temperature for 75 mm. The pH was adjusted to pH 7 with 6 N HC1 and DCM were added. The layers were separated and the organic layer was washed with water, dried over Na2504 and the solvent was removed under reduced pressure. The residue was stirred with diethyl ether for 30 mm, filtered and washed with diethyl ether to give 7.9 g (76 %) of the primary amide.1H NMR (300 MHz, d6-dmso) oe = 8.01 (s, 2H, Htriazoiyi), 7.79 (br s, 1H, NH), 7.61 (d, J =8.1 Hz, 1H, Harom), 7.40 (d, J = 8.4 Hz, 1H, Harom), 7.38 (s, 1H, Harom), 7.32 (br s, 1H, NH),2.40 (s, 3H, CH3).13C NMR (75 MHz, d6-dmso) oe = 168.6, 138.0, 135.8, 134.6, 132.0, 130.5, 129.0, 123.8,20.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 956317-36-5, its application will become more common.

Reference:
Patent; SANDOZ AG; HOeFERL-PRANTZ, Kathrin; BARTH, Roland; RICHTER, Frank; ZUPANCIC, Borut; (126 pag.)WO2016/20403; (2016); A1;,
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. 49607-51-4, name is 1-Methyl-1H-1,2,4-triazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Methyl-1H-1,2,4-triazol-3-amine

Triphosgene (0.588 g, 1.982 mmol) was added to a stirred solution of (4S)-7-(2- methylpyridin-4-yl)-2,3,4,5-tetrahydro-l,4-methanopyrido[2,3-b][l,4]diazepine (0.5g, 1.982 mmol) in tetrahydrofuran (20 mL) at 0 C and stirred for 30min. Triethylamine (0.829 mL, 5.94 mmol) and 1 -methyl- lH-l,2,4-triazol-3 -amine (0.486 g, 4.95 mmol) was added at 0 C. The reaction mixture was stirred for 48h at 70 C. The reaction mixture was cooled to 28 C, and was partitioned between water (50 mL) and DCM (50 mL). The separated organic layer was washed with water and brine. The organic layer was dried over anhydrous Na2SC”4, filtered and filtrate was evaporated to afford crude yellow solid (TLC eluent: 10% MeOH in EtOAc: Rr0.3; UV active). The crude compound was purified by (100-200 mesh) silica gel and was eluting with 5% MeOH in ethyl acetate to afford (4S)-N-(1 -methyl- H- 1 ,2,4-triazol-3 -yl)-7-(2-methylpyridin-4-yl)-3,4-dihydro- 1 ,4- methanopyrido[2,3-6][l,4]diazepine-5(2H)-car-boxamide (0.215g, 0.563 mmol, 28.4 % yield) as light yellow solid, LCMS (m/z): 377.28 [M+H]+.1H NMR (400 MHz, DMSO-i): delta 13.44 (s, 1H), 8.55 (d, J = 5.2 Hz, 1H), 8.36 (s, 1H), 7.96 (s, 1H), 7.86 – 7.61 (m, 3H), 5.44 (dd, J = 5.8, 3.0 Hz, 1H), 3.83 (s, 3H), 3.27 (d, J = 30.5 Hz, 3H), 2.95 (dd, J= 12.0, 3.2 Hz, 1H), 2.59 (s, 3H), 2.23 (ddt, J= 16.9, 9.7, 4.4 Hz, 1H), 1.91 (dt, J= 14.7, 7.4 Hz, 1H).

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 49607-51-4.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-67-7,Some common heterocyclic compound, 16681-67-7, name is 4-Bromo-2-methyl-2H-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.

4H-[ l,2,4]Triazolo[4,3-a ][ l,5]benzodiazepine, 5, 6-dihydro-l,4-dimethyl-8-( 2- methyl-2H-l,2,3- triazole-4-yl)-6-(4-cyano-phenyl) ( Compound 109). A solution of 4H- [l,2,4]Triazolo[4,3-a][l,5] benzodiazepine, 5,6-dihydro-l,4-dimethyl-8- (4,4,5,5-tetramethyl-1.3.2- dioxaborolan-2-yl)-6-(4-cyano-phenyl) (270 mg, 0.61 mmol), 4-bromo-2- methyl-2H-1.2.3- triazole (109 mg, 0.67 mmol), tetrakis(triphenylphosphine)palladium(0) (70 mg) and potassium carbonate anhydrous (337 mg, 2.44 mmol) in tetrahydrofuran (10 mL) and water (2 mL) was reacted at 100 C for 30 minutes with microwave (pressure : 17.2 bar, equipment power : 150W). The reaction mixture was diluted with ethyl acetate (50 mL), washed by brine (20 mL x 3), dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by CombiFlash (silica gel, dichloromethane / methanol = 10:1) to afford 4H-[l,2,4]triazolo[4,3-a][l,5] benzodiazepine, 5,6-dihydro-l,4-dimethyl-8-(2-methyl-2H-l,2,3- triazole-4-yl)-6-(4-cyano-phenyl) as a white solid (65 mg, 27 % ).

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-2-methyl-2H-1,2,3-triazole, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 6818-99-1, A common heterocyclic compound, 6818-99-1, name is 3-Chloro-1,2,4-triazole, molecular formula is C2H2ClN3, 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.

2.06 g (10 mmol) of 3-chloro-1,2,4-triazole was mixed with 20.6 ml of tetrahydrofuran, and 2.29 g (10 mmol) of pure 2-chloroisobutyryl chloride was added dropwise, over about 30 minutes. The mixture was stirred for 8 hours, filtered, the insoluble material was filtered off and the filtrate was concentrated to dryness under reduced pressure. 5 ml of methyl tert-butyl ether was added, stirred for 30 minutes, filtered, and the cake was dried to obtain 2.15g of product, yield 85%.

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; Ningbo Baisijia Pharmaceutical Technology Co., Ltd.; Jin Chunhua; Tang Jianbo; Wang Kedi; Zhu Qinfeng; (13 pag.)CN106866558; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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