Category: 486460-21-3

Adding some certain compound to certain chemical reactions, such as: 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, 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 486460-21-3. 486460-21-3

((c/s-1-(3-Chlorophenyl)-4-f3-(trifluoromethyl)-5.6-dihvdrori.2.4ltriazolof4.3-a1pyrazin- 7(8H)-yl1cvclohexyl)methyl)-carbamic acid tert-butyl ester and ((^ra/7s-1-(3-chlorophenyl)-4- f3-(triflupsilonoromethyl)-5.6-dihvdrof1.2.41triazolof4.3-a1pyrazin-7(8H)-vncvclohexyl>methyl)- carbamic acid tert-butyl esterSodium triacetoxyborohydride (316mg, 1.49mmol) was added to a solution of [1-(3- chlorophenyl)-4-oxo-cyclohexylmethyl]-carbamic acid tert-butyl ester (360mg, 1.07mmol) and 3-trifluoromethyl-5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine (286.4mg, 1.49mmol) in 1 ,2-dichloroethane and the mixture was stirred at room temperature for 24h. The reaction was quenched with water and the product was extracted with ethyl acetate. The organic extracts were washed with brine, dried and concentrated in vacuo to give a yellow oil. The oil was purified by flash chromatography (silica, eluting with 1 :33:66 2M ammonia in methanol:ethyl acetatexyclohexane) to afford the individual title compounds as white solids.Cis diastereoisomer:MS (ES+): 514[M+H]+.TR [HPLC, Phenomenex Luna 3 micron C18; 5-95% CH3CN+0.1%Formic acid/H2O+0.1%Formic acid for 5 min, flow 2.0 ml/min]: 3.70 min.Trans diastereoisomer:MS (ES+): 514[M+H]TR [HPLC, Phenomenex Luna 3 micron C18; 5-95% CH3CN+0.1%Formic acid/H2O+0.1%Formic acid for 5 min, flow 2.0 ml/min]: 3.57min

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 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine.

Reference:
Patent; NOVARTIS AG; WO2008/77597; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 486460-21-3 name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, 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. 486460-21-3

The resulting product is dissolved in tetrahydrofuran (200 ml) and the solution is added in about 90 minutes to a solution obtained dissolving chloroacetyl chloride (28.6 g, 253 mmol) in tetrahydrofuran (200 ml), under N2 atmosphere and under stirring. The solution is left under stirring at 25C for 1 h. After completion of the reaction, a 25% NaOH solution (80 g) is added, the phases are separated and the aqueous phase is extracted with 2×100 ml of tetrahydrofuran. The solvent is concentrated under reduced pressure to obtain 160 g of a crude, which is added with methyl-tert-butyl ether (220 ml) and the solution is heated under reflux of the solvent mixture. The solution is cooled to 10C under strong stirring for 3h. The product (56.1 g, 209 mmol, 89% yield) is a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Dipharma Francis S.r.l.; EP2270009; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

486460-21-3, 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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, A new synthetic method of this compound is introduced below.

The dihydroformed product prepared in Example 7 (1.5 g, 3.1 mmol) was added to 60 mL of 2N HCl,Reflux for 12 hours.Ice water bath cooling,The bottom of the yellow oil precipitation,Pour the upper water,The lower oily substance was dissolved in dichloromethane,A small amount of saturated sodium bicarbonate washing,Dispensing,After the organic phase is dried,With a rotary evaporator evaporated to dry yellow liquid,Directly take the next step.Ice water bath,A small amount of the above crude product (0.6 g, 1.4 mmol) was dissolved in dichloromethane (10 mL)Plus DIPEA (Chinese name: N, N-diisopropylethylamine, 452 mg, 3.5 mmol)And 1-hydroxybenzotriazole (19 mg, 0.14 mmol)Trimethylacetyl chloride (210 mg, 1.75 mmol) was then added dropwise.After 0.5 hours,A solution of 3- (trifluoromethyl) -5,6,7,8-tetrahydro- [1,2,4] triazolo [4,3-a] pyrazine (CAS No. 486460-21-3, 296 mg, 1.54 mmol),Continue stirring at room temperature overnight.The next day,Washed,Saturated sodium bicarbonate wash,Organic phase dry,With a rotary evaporator to dry the crude product,1.14 g (yield: 67%, HPLC purity 99%) was obtained by recrystallization (petroleum ether / ethyl acetate = 20/1) as a white solid amidated product.

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; Zhejiang Xinhecheng Co., Ltd.; Zhejiang University; Zhang Yuhong; Yao Jinzhong; Qian Hongsheng; Lin Cong; Lu Guobin; Tang Jiaxing; Shen Chuang; (15 pag.)CN103819475; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C6H7F3N4, 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. 486460-21-3

Step: 20aSynthesis of 7-(4-Nitro-phenyl)-3-trifluoromethyl-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3- ajpyrazine.Procedure:K2C03 (4.4g, 0.053mol), followed by l-Fluoro-4-nitro-benzene (1.5g, 0.0177mol) was added to a solution of 3-Trifluoromethyl-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3- a]pyrazine (3.2g, 0.0230mol) in DMF (15ml), and the flask was stirred for 6hrs at 80C. The reaction was monitored by the TLC (20% ethylacetate in hexane). From the resulting reaction mixture DMF was distilled, the residue was purified by column chromatography (using silica gel of mesh size of 60-120, 20% ethylacetate in hexane as eluant) to afford 1.2g (36.36% yield) of 7-(4-Nitro-phenyl)-3-trifluoromethyl-5,6,7,8-tetrahydro-[l ,2,4]triazolo[4,3- ajpyrazine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 486460-21-3, its application will become more common.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SENGUPTA, Saumitra; RAJAGOPALAN, Srinivasan; BELAVAGI, Ningaraddi; RAMACHANDRA, Muralidhara; WO2012/59932; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C6H7F3N4, 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. 486460-21-3

Using Procedure Y-3 (Table 5) with compound 479 the title compound 480 was obtained (550 mg, 49%) as a beige solid. MS (m/z): 343.4 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 486460-21-3, its application will become more common.

Reference:
Patent; Forum Pharmaceuticals, Inc.; Rogers, Kathryn; Patzke, Holger; (315 pag.)US2017/749; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 486460-21-3 as follows. 486460-21-3

The compound of formula 7 (1.3 g, 0.01 mol) was reacted withCompound 9 (1.9 g, 0.01 mol) was added to a 50 ml two-necked flask,Join20 ml of methylene chloride,Added HOBt at -10-10 (1.49,0.011mol) andEDC.HCl (2.9 g, 0.015 mol) The reaction mixture was stirred at room temperature for 8 hours,After completion of the reaction, 15 mL of aqueous NaHCO3 solution was added and the organic phase was saturatedWashed with brine, dried over anhydrous sodium sulfate, concentrated, purified by column chromatography,To give 2.67 g of the compound of formula b,The yield was 89.1%.

According to the analysis of related databases, 486460-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; Zhu Guoliang; He Qian; Qian Lingfeng; Xu Yingzhou; Yan Pucha; (13 pag.)CN106146514; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., 486460-21-3

Comparative Example 1: Preparation of Compound of formula 2 wherein R is Boc, according to the method disclosed in U.S. Patent No. 6,699,871, Example 7, STEP A [42] (R)-3-Boc-amino-4-(2,4,5-trifluorophenyl)-butanoic acid (50.1mg, 0.15mmol) was dissolved in dichloromethane (2.5ml) and 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-alpha]pyrazine (39.2mg, 0.20mmol) was added thereto. While maintaining a temperature of 0 to 5C, HOBT (17.2mg, 0.21mmol) was added to the mixture, followed by reaction for 10 minutes. Thereafter, EDC (48.3mg, 0.25mmol) was added at 0C, and the reaction mixture was warmed to room temperature and stirred for 14 hours. After the reaction was completed, the reaction liquid was concentrated under reduced pressure and a desired compound was purified by column chromatography eluting with 100% ethyl acetate to afford 29mg (yield: 47.5%) of the title compound as a solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ST PHARM CO., LTD.; LIM, Geun Gho; CHANG, Sun Ki; BYEON, Chang Ho; WO2012/99381; (2012); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

486460-21-3, A common heterocyclic compound, 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C6H7F3N4, 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 26 2-((5-(2-(3,4-dimethoxyphenyl)propan-2-yl)-4-(4-fluorophenyl)-4H-l,2,4-triazol-3- yl)thio)-l-(3-(trifluoromethyl)-5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazin-7(8H)- yl)ethanone 2-((5-(2-(3,4-dimethoxyphenyl)propan-2-yl)-4-(4-fluorophenyl)-4H-l,2,4-triazol-3- yl)thio)acetic acid and 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[l ,2,4]triazolo[4,3- a]pyrazine was dissolved in DMF and then cooled to 0 C followed by addition of HBTU and DIPEA, reaction was monitored by TLC and then reaction was quenched by water and compound was extracted by ethyl acetate. Product was purified by column chromatography. NMR (DMSO-ck, 400 MHz): 7.10-7.03 (m, 2H), 6.77-6.70 (m, 3H), 6.40 (d, J = 5.6 Hz, 2H), 5.03 (s, 1H), 4.84 (s, 1H), 4.24-4.19 (m, 4H), 4.05-4.00 (m, 2H), 3.72 (s, 3H), 3.60 (s, 3H), 1.53 (s, 6H). m/z Relative intensities: 606.1 (M+)100 %.

The synthetic route of 486460-21-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CADILA HEALTHCARE LIMITED; AGARWAL, Sameer; DESAI, Ranjit, C.; WO2013/164838; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., 486460-21-3

VI (2.0g, 5.0mmol) and 3- (trifluoromethyl) -5,6,7,8-tetrahydro – [1,2,4] triazolo [4,3-a] pyrazine (of 0.912 g , 4.7mmol) Was dissolved in 20ml of anhydrous N, N- dimethylformamide was added HOBt (0.770g, 5.7mmol) and EDC ¡¤ HCL (1.092g, 5.7mmol), stirred at room temperature 20h. After the reaction was added 20ml of water and 20ml of ethyl acetate, there Phase was washed with water 3 times, washed three times with saturated aqueous sodium carbonate solution, the organic phase was dried over anhydrous sodium sulfate, suction filtered, and concentrated to give yellow Colored foamy solid 2.967g, crude yield> 100%, recrystallized from ethyl acetate, filtration and drying to give a yellow solid 1.827g, Recrystallization yield of 63.6%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Shanghai Institute Of Pharmaceutical Industry; China State Institute of Pharmaceutical Industry; Meng, Xiangguo; Cai, Zhengyan; Zhou, Weicheng; Jiang, Jingzhang; Zhu, Yijun; Ge, Yuanyuan; Yan, Pingping; (32 pag.)CN103172635; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., 486460-21-3

To a solution of (R)-3-[(tert-butyloxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)- butanoic acid (1.36 g, 4.080 mmol) in acetonitrile (20 ml) was added Diisopropylethylamine (2.47 g, 19.12 mmol) and 1 ,1-Carbonyl diimidazole (0.94 g, 5.82 mmol) at room temperature. The reaction mixture was stirred for 30 min at room temperature. S-iTrifluoromethylJ-S.ej.e-tetrahydro-l ,2,3-triazolo[4,3- a]pyrazine (0.750 g, 3.88 mmol) was added to the above reaction mixture at room temperature. The reaction mixture was heated to 65-70C for 22 h. After completion of the reaction, the mixture was concentrated under vacuum and the crude mass was dissolved in ethyl acetate (15 ml) and washed with 5% aqueous NaHC03 solution followed by twice with water (2 x 30 ml). The ethyl acetate layer was concentrated under reduced pressure to get crude mass and recrystallized from mixture of 10 % ethyl acetate and petroleum ether (50 ml) to get 1.5 g (82%) of tert-butyl{(1 R)-3-oxo-1 -(2,4,5-trifluorobenzyl)-3-[3-(trifluoromethyl)-5-6- dihydro[1 ,2,4] triazole[4,3-a]pyrazin-7(8H)-yl]propyl}carbamate.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; PANACEA BIOTEC LTD; JAIN, Rajesh; RAO, Jagadeeshwar, R; RAO, Siripragada, Mahender; WO2012/35549; (2012); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem