Day: May 17, 2021

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. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, A new synthetic method of this compound is introduced below., Quality Control of 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: A mixture of dimedone (1 mmol), aldehyde or isatin (1 mmol) and 4-phenylurazole (1 mmol), and catalyst (0.01 g, 5 mol%) in water (5 mL) was refluxed. After completion of the reaction that was monitored by TLC (EtOAc:n-hexane, 1:3), the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with water and cooled with ethanol to afford the pure product.

The synthetic route of 15988-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Seyyedhamzeh, Mozhdeh; Shaabani, Shabnam; Hamidzad Sangachin, Mona; Shaabani, Ahmad; Research on Chemical Intermediates; vol. 42; 4; (2016); p. 2845 – 2855;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic 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. Recommanded Product: 2-(2H-1,2,3-Triazol-2-yl)benzoic acid

Step C: (2-(2H-1,2,3-triazol-2-yl)phenyl)((1S,4R,6R)-6-((3-(trifluoromethyl)pyridin-2-yl)oxy)-2-azabicyclo[2.2.1]heptan-2-yl)methanone To the title compound of step B (25 mg) and intermediate A-1 (18 mg, 0.093 mmol) in DMF (0.8 mL) was added DIPEA (75 muL, 0.44 mmol) and HATU (36 mg, 0.093 mmol), and the reaction mixture was stirred at room temperature for 1 h. The reaction was quenched by the addition of H2O and the aqueous layer was extracted with EtOAc (3*). The combined organics were washed with H2O, 5% aqueous LiCl, brine, dried with Na2SO4, filtered, and concentrated. Purification via silica gel chromatography (0-60% EtOAc in hexanes) gave the title compound (29 mg). MS (ESI) mass calcd. C21H18F3N5O2, 429.1; m/z found 430.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d, Compound present as a mixture of rotamers, (0.76:0.24), major rotamer reported) delta 7.93-7.82 (m, 4H), 7.81 (s, 2H), 7.07 (dd, J=7.7, 1.5 Hz, 1H), 6.93-6.86 (m, 1H), 6.75 (td, J=7.6, 1.2 Hz, 1H), 5.04 (dt, J=10.2, 3.4 Hz, 1H), 4.15-4.04 (m, 1H), 3.66 (dt, J=10.9, 3.3 Hz, 1H), 3.38 (dd, J=10.9, 1.4 Hz, 1H), 2.66-2.60 (m, 1H), 2.27-2.15 (m, 1H), 1.48 (dt, J=13.3, 3.6 Hz, 1H), 1.44-1.37 (m, 1H), 1.36-1.28 (m, 1H).

The synthetic route of 2-(2H-1,2,3-Triazol-2-yl)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; GELIN, Christine F.; LEBOLD, Terry P.; SHIREMAN, Brock T.; US2014/275118; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 6818-99-1, 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. 6818-99-1, name is 3-Chloro-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

500 mg of intermediate 4, 60% sodium hydride(Oily) 60 mg, and DMF 2.5 mL,Under ice-cooling, 141 mg of 3-chloro-1 H-1,2,4-triazole was added. After stirring for 2.5 hours under ice cooling,Saturated multilayer aqueous solution was poured into the reaction mixture,And extracted with ethyl acetate. The organic layer was washed with water,And washed with saturated brine,And dried over anhydrous sodium sulfate.The obtained organic layer was dried under reduced pressure.The obtained residue was subjected to silica gel chromatography,435 mg of the present compound 9 described below was obtained.

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

Reference:
Patent; Sumitomo Chemical; Ikari, Kaori; (123 pag.)JP2019/6686; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 217448-86-7,Some common heterocyclic compound, 217448-86-7, name is Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, molecular formula is C11H9F2N3O2, 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 6: Preparation of Rufinamide Methyl l-(2, 6-difIuorobenzyl)-lH-l,2,3-triazole- 4-carboxylate (19 g) was dissolved in methanol (285 ml) at 65-70C. Added dropwise 20% liq NH3 (150 ml) over a period of 30 min. The mixture was then stirred at 65-70C for 5-6 hours. After the completion of reaction, as monitored by TLC, the reaction mixture was cooled to room temperature. The solid was filtered, washed with water and dried under vacuum at 65C to give rufinamide (13.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, its application will become more common.

Reference:
Patent; AARTI INDUSTRIES LIMITED; DESAI, Parimal, Hasmukhlal; SALVI, Narendra, Jagannath; SUBRAMANIAN, Seetharaman; WO2014/72992; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, 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. Quality Control of 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: Dimedone (0.14 g, 1 mmol), benzaldehyde (0.1 g, 1 mmol), and 4-phenylurazole (0.177 g, 1 mmol) were mixed with PEG-SO3H (0.6 g, 0.1 mmol) and the obtained mixture was stirred magnetically at 80 C for 40 min. After the completion of the reaction warm water (20 mL) was added and the mixture stirred for about 5 min. The insoluble crude product was filtered and recrystallized from EtOH/H2O 4:1 and the pure product was obtained (0.352 g, 91%). In order to recover the catalyst, the filtrate was dried under reduced pressure and recovered catalyst was washed with diethyl ether and reused after drying under reduced pressure. The equivalent procedure was used for the synthesis of triazolo[1,2-a]indazole-tetraones.

The synthetic route of 15988-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasaninejad, Alireza; Zare, Abdolkarim; Shekouhy, Mohsen; Tetrahedron; vol. 67; 2; (2011); p. 390 – 400;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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 16681-70-2, Safety of 1H-[1,2,3]Triazole-4-carboxylic acid

Example 20 3-{(R)-3-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-[(3H-[1,2,3]triazole-4-carbonyl)amino]propyl}tetrahydrofuran-3-carboxylic Acid (isomers a and b) [0453] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer a; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature and when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer a; 7.8 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=473.0. Retention time: 4.73 min. [0455] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer b; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature. When the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer b; 2.9 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=472.9. Retention time: 4.77 min. [0456] LC/MS Method: flow rate: 1.5 mL/min; Buffer A: 0.1% TFA/H2O; Buffer B 0.1% TFA/MeCN; gradient elution from 5-100% B over 9.6 min, then 100% B for 1.0 minute, detection at 254 nm.

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

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 28938-17-2, name is 4,5-Dibromo-2-methyl-2H-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. HPLC of Formula: C3H3Br2N3

Intermediate 14d (0551) 5-Bromo-2-methyl-2H- 1 ,2,3-triazole-4-carboxylic acid (0552) A solution of 4,5-dibromo-2-methyl-2H-l,2,3-triazole (Intermediate 14e; 144 g, 597.81 mmol) in anhydrous THF (1.5 L) was cooled to -30 C under nitrogen atmosphere and i- PrMgCl (330 mL, 658 mmol, 2M in THF) was added dropwise. The solution was stirred at -30 C for 1 hour, and then bubbled with C02 for 3 hours at <10 C. The reaction was then stirred at 25 C for 16 hours. The mixture was quenched with aqueous HC1 (-3000 mL, 0.1M) to pH = ~2 and extracted with EtOAc (3 L x 3). The organic phase was then extracted with aqueous NaOH (0.1M, 2 L x 3). The aqueous phase was then added to aqueous HC1 (~6 L, 0.1M) to pH=~2 and extracted with EtOAc (3L x 3). The organic phase was dried with Na2S04 and concentrated under vacuum to give 5-bromo-2-methyl- 2H-l,2,3-triazole-4-carboxylic acid (Intermediate 14d; 105 g, 85.26% yield) as a white solid. lH NMR (DMSO, 400 MHz) delta 4.23 (s, 3H). 13C-NMR (400MHz, DMSO) delta 160.86, 138.23, 124.52, 43.38. The synthetic route of 4,5-Dibromo-2-methyl-2H-1,2,3-triazole has been constantly updated, and we look forward to future research findings. Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; FERON, James, Lyman; (80 pag.)WO2017/80980; (2017); 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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C2H5N5

EXAMPLE 31 3,5-Diamino-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole The synthesis method of Example 1-(3) was applied. 3,5-Diamino-1H-1,2,4-triazole (11.0 g), dimethylformamide (100 ml) and methyl isothiocyanate (10.0 g) were used as reagents. After the reaction, recrystallization from ethyl acetate gave 13.0 g of white powdery crystals (yield (68percent). Melting point: 176°-178° C. IR (KBr): 3430, 3280, 1620, 1520 cm-1 1 H-NMR (DMSO-d6) delta: 2.98 (3H, d, J=4.4 Hz), 5.63 (2H, brs), 8.14 (2H, brs),9.19 (1H, m)

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

Reference:
Patent; The Green Cross Corporation; US5750545; (1998); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, molecular formula is C3H4N4O2, 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. SDS of cas: 3641-13-2

General procedure: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3641-13-2, its application will become more common.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
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 1455-77-2 as follows. category: Triazoles

1H-1,2,4-Triazole-3,5-diamine (12.4 g, 0.125 mol) was dissolved in AcOH (50 ml), and diethyl 2-(ethoxymethylene)malonate (32.5 g, 0.15 mol) was added. The solution was refluxed overnight, then cooled, filtered, and dried to give Key Intermediate VI (22 g, 79percent) as a white solid.

According to the analysis of related databases, 1455-77-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WOLKERSTORFER, Andrea; Szolar, Oliver; Handler, Norbert; Cusack, Stephen; Sauvaitre, Thibault; Simon, Celine; Morice, Christophe; Giethlen, Bruno; Langer, Thierry; Smith, Mark; So, Sung-Sau; Classen-Houben, Dirk; Buschmann, Helmut; US2013/317021; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics