Day: April 8, 2021

Some common heterocyclic compound, 74733-90-7, name is 2-(4-Bromophenyl)-2H-1,2,3-triazole, molecular formula is C8H6BrN3, 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 74733-90-7

Potassium acetate (391 mg, 3.98 mmol) was added to a solution of 2-(4- Bromophenyl)-2H-1 ,2,3-triazole (1.0 equivalent), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi- 1 ,3,2-dioxaborolane (1.20 equivalents), and [1 , 1 ‘-bis-(diphenylphosphino)ferrocene]- dichloropalladium (II) dcm complex (0.30 equivalents) in 1 ,4-dioxane in a vial. The vial was capped and heated to 80C and stirred at this temperature overnight. [1 ,T-bis- (diphenylphosphino)ferrocene]-dichloropalladium (II) dcm complex (0.30 equivalents) was added to the reaction and the mixture was reheated to 80C and stirring was continued at this temperature overnight. The reaction was cooled, diluted with ethyl acetate and water, filtered through celite and the filter pad was washed with ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organics were dried (MgSCb), filtered, and concentrated. The crude was purified via flash chromatography using an Analogix SF15-24g column and ethyl acetate in heptane (30-80%) as the eluant to afford the title compound was converted to the title product. The title compound was obtained as an orange solid (240.6 mg, 78%) LC-MS m/z 272.4 (M+1 ) 1 H NMR (CDCb, 400 MHz) d ppm 1 .37 (s, 12 H) 7.83 (s, 2 H) 7.94 (d, J=8.59 Hz, 2 H) 8.10 (d, J=8.59 Hz, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 74733-90-7, its application will become more common.

Reference:
Patent; PFIZER INC.; BROWN, Matthew, Frank; CHE, Ye; MARFAT, Anthony; MELNICK, Michael, Joseph; MONTGOMERY, Justin, Ian; JOHNSON, Timothy, Allan; EWIN, Richard, Andrew; UCCELLO, Daniel; REILLEY, USA; BRAISH, Tamim, Fehme; (77 pag.)WO2019/178305; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 217448-86-7, These common heterocyclic compound, 217448-86-7, name is Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-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.

Example 8Synthesis of Compound (I)1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxyamide (Rufinamide); Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate (II) (10.6 g, 41.9 mmoles), prepared as reported in Example 7, is dissolved in methanol (10 ml) and treated at room temperature under stirring with a 30% ammonia aqueous solution (40 ml), then the reaction mixture is refluxed and kept under stirring for 3 hours. The mixture is cooled to 20 C., then diluted with water, filtered, and the resulting white solid is washed with water and dried in a static dryer at 50 C. Rufinamide (8.7 g) is obtained as a crystalline white solid in 87% yield.1H NMR (400 MHz, DMSO-d6), delta ppm: 8.56 (s, 1H), 7.87 (bs, 1H), 7.60-7.43 (m, 2H), 7.20 (m, 2H), 5.72 (s, 2H).

Statistics shows that Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate is playing an increasingly important role. we look forward to future research findings about 217448-86-7.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; US2010/234616; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 15988-11-1, These common heterocyclic compound, 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, 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.

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

Synthetic Route of 288-36-8,Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-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.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), Cs2CO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-5, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for A-5: 1HNMR (500 MHz, DMSO-d6) d 12.98 (br s , IH), 8.04 (s, 2H), 7.72-7.45 (m, 3H), 2.41 (s, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-1,2,3-Triazole, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; COLEMAN, Paul, J.; SCHREIER, John, D.; WO2010/48014; (2010); 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 16681-70-2

1,2,3-Triazole-4-carboxylic acid (0.0274 g, 0.242 mmol), DIPEA (169 muL, 969 mumol) and HATU (92 mg, 242 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 2-piperidin-1-yl-ethyl ester (103 mg, 242 mumol), predissolved in DMF (0.2 mL) and DIPEA (0.5 eq.). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product was purified by preparative HPLC and lyophilized to yield the title compound (40 mg; purity 95%). MS m/z [M+H]+ calc’d for C29H37N5O4, 520.28. found 520.4.

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; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 13273-53-5,Some common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-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.

To a mixture of 6-1 (50 mg, 0.13 mmol, 1.0 eq) and 6-la (28 mg, 0.17 mmol, 1.30 eq) in dioxane (2 mL) and H20 (0.5 mL) was added Na2C03 (38 mg, 0.36 mmol, 2.7 eq) and Pd(dppf)Cl2 (10 mg, 13 umol, 0.1 eq) in one portion under N2. The mixture was stirred at 100 C for 16 h. LCMS showed the starting material was consumed completely and one peak with desired MS was detected. The reaction mixture was concentrated under reduced pressure to remove solvent, and then added CH3CN (5 mL), filtered to give a black-brown liquid. The residue was purified by prep-HPLC. LCMS and XH NMR confirmed Compound 6 was obtained (2.06 mg, 5.5 umol, 4.2% yield, HC1). LCMS (ESI): RT = 0.752 min, mass calcd. For Ci6H22N402S, 334.15 m/z found 334.9[M+H]+.1H NMR (400MHz, DMSO-c) 58.76 (s, 1H), 8.34 (br s, 1H), 7.95 (d, J=2.00 Hz, 1H), 7.60 (dd, J=8.80, 2.00 Hz, 1H), 6.91 (d, J=8.80 Hz, 1H), 4.13 (s, 3H), 3.11 (s, 3H), 2.60 – 2.53 (m, 1H), 2.02 – 1.89 (m, 2H), 1.74 – 1.63 (m, 2H), 1.62 – 1.51 (m, 1H), 1.49 – 1.26 (m, 5H).

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

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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 61-82-5

General procedure: A mixture of aldehyde (1.0 mmol), dimedone (1.0 mmol),1H-1,2,4-triazol-3-amine (1.0 mmol) and nano-AlPO4(SO3H) (0.1 g) was stirred in the acetonitrile (4.0 mL)at 50 C for an appropriate time. After the completion of thereaction as indicated by TLC, dichloromethane was addedto the solidified mixture and the insoluble catalyst was separatedby centrifugation. Evaporation of the solvent from thefiltrate and recrystallization of the solid residue from hot ethanolafforded the pure products in good to excellent yields

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61-82-5, its application will become more common.

Reference:
Article; Sharghi, Hashem; Aboonajmi, Jasem; Aberi, Mahdi; Shiri, Pezhman; Journal of the Iranian Chemical Society; vol. 15; 5; (2018); p. 1107 – 1118;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 61-82-5, These common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, 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.

General procedure: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

The synthetic route of 61-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7343-33-1, 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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

2 – (6 – chloro – 3 – ethanesulfonyl – pyridin – 2 – yl) – 3 – methyl – 6 – trifluoromethyl – 3 H – imidazo [4,5 – b] pyridine300 mg,Potassium carbonate133 mg, and N, N-dimethylformamide 3 mL, 3-boule132 mg of lomo-1 H-1,2,4-triazole was added. And the mixture was stirred for 2.5 hours under ice coolingAfter that, a saturated multilayer aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. Water and saturated organic layerWashed with Japanese salt water, and dried with anhydrous sodium sulfate. The obtained organic layer was dried under reduced pressure.The obtained residue was subjected to silica gel chromatography, and the following compound 3 described below was separated by 370 mg.

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, 5-Bromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; NISHIGUCHI, NAONOBU; SUNAMURA, EIRIKI; (25 pag.)JP2017/52702; (2017); 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. 3179-31-5, name is 1H-1,2,4-Triazole-3-thiol, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C2H3N3S

A. 3-(3-Bromophenyl)-lH-l,2,4-triazoIe. In a sealed tube, a solution of 3- bromobenzaldehyde (1.Og, 5.0 mmol) was treated with dimethylformamide dimethylacetal (5 mL) at 100 C for 6 h. Upon completion of the reaction, the volatiles were removed under reduced pressure. The crude product was treated with hydrazine (2 mL) and acetic acid (10 drops) at room temperature for 1 h. The volatiles were removed under reduced pressure. The crude product was dried under high vacuum, and used without further purification in the next step. MS (ESI) m/z 226.1 [M+l]+.

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 3179-31-5.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics