Day: April 30, 2021

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 1157938-97-0 as follows. category: Triazoles

To a solution of diisoproplylamine (120 g) in dry THF (1500 ml) 1.6 M solution of butyllithium in hexane (730 ml) was slowly added at -40 C. under nitrogen atmosphere. The mixture was allowed to warm up to -20 C. for ca. 10 min, then re-cooled to -78 C. and to this LDA-solution N,N-bis(2,4-dimethoxybenzyl)thiopropionamide (390 g), dissolved in dry THF (500 ml) was slowly added that the reaction temperature did not exceed -40 C. (exothermic reaction, cooling). After addition the mixture was stirred at -40 C. for ca. 1 hr, then at this temperature 1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (223 g), dissolve in dry THF (400 ml), was slowly added, the reaction mixture stirred for another 2 hrs, then within ca. 1 hr warmed up to -20 C. and finally poured on an aqueous phosphate buffer solution (pH 7). The aqueous phase was extracted 3 times with ethylacetate (500 ml) and the combined organic phases dried twice with sodium carbonate, filtered and evaporated under reduced pressure providing 3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-N,N-bis(2,4-dimethoxybenzyl)thiobutyramide: 590 g (96% yield) as a single diastereomer. This crude material was dissolved at 0 C. under cooling in a mixture of methylenechloride (1000 ml) and triflic acid (150 g) and slowly triethylsilane (500 g) was added within ca. 3 hrs keeping the temperature under 10 C. After the reduction was finished the reaction mixture was poured very slowly on aqueous saturated sodium bicarbonate solution, extracted 3 times with ethylacetate (500 ml), dried with sodium sulphate, filtered and evaporated under reduced pressure providing the crude title compound: 250 g (80% yield). The analytical data were identical with published one for (2R,3R)-enantiomer in U.S. Pat. No. 6,300,353 and WO99/45008.

According to the analysis of related databases, 1157938-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Carbo-Design LLC; US2011/87030; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-70-2,Some common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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.

[0713] 3H-1,2,3-triazole-5-carboxylic acid (2.5 mg, 22f.tmol) was combined with HATU (8.4 mg, 22 fllllOl) in DMF(0.3 mL) and stirred for 10 minutes; Et3N (1 eq.) was addedand the mixture was stirred for 1 minute. Compound 2 (22f.tmol) was dissolved in DMF (0.5 mL) and Et3N (3.1 f.LL, 22f.tmol) was added, followed by addition of the activated acidsolution. The mixture was stirred for 30 minutes, concentrated,and purified by preparative HPLC to yield the titlecompound. MS m/z [M + Ht calc’ d for C27H31 ClFN 50 4 , 544.21; found 544.2.

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-4-carboxylic acid, its application will become more common.

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

Application of 4928-87-4,Some common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, molecular formula is C3H3N3O2, 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 1: N-[2-[[4-[(lR,3S)-3-[[( lR)-l-(4-Fluoro-3-methoxy-phenyl) ethyl]-amino]cyclopentyl]benzoyl]amino]ethyl]-lH-l,2,4-triazole-3- carboxamide (Compound 101)To a solution of Intermediate 4 (719 mg, 1.8 mmol) in dry DMF (12 mL) was added HOBt (276 mg, 2 mmol) and EDAC (517 mg, 2.7 mmol), and the mixture was stirred at rt for 4 hours. lH-l,2,4-triazole-3-carboxylic acid (200 mg, 1.8 mmol) was then added, and stirring was continued overnight at rt. The solvent was removed under reduced pressure and the crude purified by flash chromatography (30% MeOH/DCM), affording the title compound in 78% yield. *H NMR (300 MHz, DMSO) delta 8.70 (br m, IH), 8.48 (br m, IH), 8.41 (s, IH), 7.76 (d, J = 8.2 Hz, 2H), 7.31 (d, J = 8.2 Hz, 2H), 7.17 (dd, J = 8.6, 1.6 Hz, IH), 7.10 (dd, J = 11.5, 8.3 Hz, IH), 6.89 (ddd, J = 8.1, 4.4, 1.8 Hz, IH), 3.84 (s, 3H), 3.78 (q, J = 6.6 Hz, IH), 3.46 (br m, 4H), 3.04 – 2.85 (m, 2H), 2.15 – 1.54 (m, 6H), 1.43 – 1.19 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2,4-Triazole-3-carboxylic acid, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; MANSSON, Kristoffer; WO2012/69421; (2012); 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. 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9N3O

General procedure: Into a round-bottom flask equipped with a magnetic stirring bar already containing a solution of 10mmolof 1,2,3-triazoles type 12 in 27.5mL of DMSO was added 11mmolof IBX. This mixture was stirred at room temperature for 4h. Next, distilled water (20mL) was added, and stirring was continued for 15minat room temperature. Subsequently, the mixture was filtered, extracted with ethyl acetate and dried over with MgSO4. The product was purified via silica-gel column chromatography using gradient mixture of hexane-ethyl acetate to afford the pure derivatives 11 and 15a-b.

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 103755-58-4.

Reference:
Article; Gonzaga, Daniel; Senger, Mario Roberto; Da Silva, Fernando De Carvalho; Ferreira, Vitor Francisco; Silva Jr., Floriano Paes; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 461 – 476;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 16681-65-5, 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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows.

The title compound was prepared according to the patent application WO2008/135826. To a 50 mL 2-necked flask containing 1-methyl-1H-1,2,3-triazole (1.0 g, 12.0 mmol, prepared according to PCT Int. Appl., 2008098104) was added THF (45 mL) and the colorless solution was cooled to -40 C. Then, n-BuLi (2.5 M in hexanes, 4.8 mL) was added dropwise which afforded a dark reddish-brown viscous solution. The mixture was stirred between -30 to -20 C. for 45 minutes, then neat DMF (3 mL, 38.5 mmol) was introduced at -10 C. The mixture was allowed to warm up to room temperature and stirred for 60 minutes, followed by pouring into water. The aqueous portion was extracted with EtOAc (4*50 mL) and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The aqueous portion was back-extracted with DCM (3*50 mL) and dried as above. The combined organics were concentrated to give a light brown oil that was much more UV active than the starting material. TLC in either 25% CH3CN-DCM or 25% EtOAc-DCM showed the product to have a slightly higher Rf than the starting material. Chromatography on silica gel (100% DCM increasing to 25% CH3CN-DCM) provided the titled material as a colorless oil.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-1,2,3-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); 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. 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, A new synthetic method of this compound is introduced below., name: 5-Methyl-4H-1,2,4-triazol-3-amine

General procedure: Solution A. A solution of KOH (0.56 g, 0.01 mol) and potassium salt of ethyl nitrocyanoacetate (1.96 g, 0.01 mol) in2 (8 ml) was stirred at room temperature for 3 h, then kept overnight. 4 M aqueous KOAc (8 ml, 0.03 mol) was added to the resulting solution, and the mixture cooled to 5. A mixture of 3-aminoazole 1a-i (0.010 mol), EtOH (10 ml),H2O (10 ml), and concentrated HCl (2.5 ml, 0.030 mol)was treated with a solution of NaNO2 (0.759 g, 0.011 mol)in H2O (3 ml) at -5 . The reaction mixture was kept at this temperature for 10 min, then added to the solution A. The mixture was kept at room temperature for 1 h; the formed precipitate was filtered, stirred with 40% aqueous H2SO4 (10 ml) (AcOH (10 ml) was used for compound 4e), filtered, and dried. The obtained hydrazone 3a-i was heated under reflux in DMF for 3 h. The solvent was evaporated, the residue triturated in water, filtered, and dried.

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:
Article; Voinkov, Egor K.; Ulomskiy, Eugeny N.; Rusinov, Vladimir L.; Chupakhin, Oleg N.; Gorbunov, Evgeny B.; Drokin, Roman A.; Fedotov, Victor V.; Chemistry of Heterocyclic Compounds; vol. 51; 11-12; (2015); p. 1057 – 1060; Khim. Geterotsikl. Soedin.; vol. 51; 11-12; (2015); p. 1057 – 1060,4;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application 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.

Under anhydrous operation, 1H-1,2,3-triazole (2.0 g, 28.9 mmol) was weighed into a 100 mL eggplant-shaped flask, and 30 mL of anhydrous THF was added.NaH (1.065 g, 43.1 mmol) was added portionwise under N2 aq ice bath and stirred at 0 C for half an hour.To the reaction system was added 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl, 7.6 mL, 43.1 mmol).After the addition was completed, the mixture was stirred at room temperature for 10 h.The reaction was completed by TLC, quenched with water and extracted with ethyl acetate (2¡Á100 mL).The organic phases were combined, washed once with brine, dried over anhydrous sodium sulfate and evaporated.Separation using a column (petroleum ether: ethyl acetate = 10:1),3.6 g of a colorless liquid were obtained in a yield of 74.2%.

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; China Pharmaceutical University; Xiang Hua; Huang Ali; Wang Chong; (19 pag.)CN108707177; (2018); A;,
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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Product Details of 41253-21-8

1.4: tert-butyl 4-cyclohexyl-4-(1H-1,2,4-triazol-1-ylmethyl)piperidine-1-carboxylate 7.83 g of tert-butyl 4-cyclohexyl-4-{[(methylsulphonyl)oxy]methyl}-piperidine-1-carboxylate and 5.68 g of sodium 1,2,4-triazole are introduced into a 100 ml round-bottomed flask under N2. 42 ml of dimethylformamide are added. After reaction in a microwave at 150 C. for 1 h 30 min and with a power of 150 W, the product is hydrolyzed and extracted with ethyl acetate until the aqueous phase is completely depleted. The organic phase is washed with H2O and concentrated to dryness. After crystallization from hexane, 4.42 g of tert-butyl 4-cyclohexyl-4-(1H-1,2,4-triazol-1-ylmethyl)piperidine-1-carboxylate are obtained. 1.5: 4-cyclohexyl-4-(1H-1,2,4-triazol-1-yl-methyl)piperidine 11.2 g of tert-butyl 4-cyclohexyl-4-(1H-1,2,4-triazol-1-ylmethyl)-piperidine-1-carboxylate are placed in 80 ml of 4N hydrochloric acid in dioxane. The reaction medium is stirred for 16 h at ambient temperature. After evaporation to dryness, the precipitate obtained is filter-dried and rinsed with diethyl ether. The hydrochloride thus obtained is dried over P2O5 under reduced pressure. 9.65 g of 4-cyclo-hexyl-4-(1H-1,2,4-triazol-1-ylmethyl)piperidine are obtained.

The synthetic route of 41253-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2007/149562; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 61-82-5,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.

General procedure: A mixture of 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1.0 mmol), arylaldehyde (1.0 mmol), dimedone (1.0 mmol), and 15 mol % p-TsOH.H2O was stirred in 5 cm3 acetonitrile as solvent at 40-50 C for the appropriate time (Table 3). The progress of the reaction was monitored by TLC. After completion of the reaction, a thick precipitate was obtained. The solid product was filtered off and washed with acetonitrile and subsequently dried in air. The pure product was characterized by conventional spectroscopic methods.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-1,2,4-Triazol-5-amine, its application will become more common.

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Monatshefte fur Chemie; vol. 145; 12; (2014); p. 1967 – 1973;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 49607-51-4, A common heterocyclic compound, 49607-51-4, name is 1-Methyl-1H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, 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.

3-Chloro-4-methylfuran-2,5-dione (625 mg, 4.27 mmol, 1.00 equiv) and 1-methyl-1H-1,2,4-triazole-3-amine (419 mg, 4.15 mmol, 1.00 equiv) were dissolved in toluene (10 ml), 4-toluenesulfonic acid monohydrate (12 mg, 0.06 mmol, 0.02 equiv.) was added and the mixture was stirred under microwave conditions at a temperature of 100 C. for 30 minutes. After cooling to room temperature, water and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 3-chloro-4-methyl-1-(1-methyl-1H-1,2,4-triazol-3-yl)-1H-pyrrole-2,5-dione in the form of a colorless solid (110 mg, 11% of theory). 1H-NMR (400 MHz, d6-DMSO delta, ppm) 8.13 (s, 1H), 3.80 (s, 3H), 2.09 (s, 3H).

The synthetic route of 49607-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; Bayer Aktiengesellschaft; FRACKENPOHL, Jens; HELMKE, Hendrik; FRANKE, Jana; REINGRUBER, Anna Maria; MACHETTIRA, Anu Bheemaiah; GATZWEILER, Elmar; ROSINGER, Christopher Hugh; SCHMUTZLER, Dirk; DIETRICH, Hansjoerg; LUEMMEN, Peter; (96 pag.)US2019/330192; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics