Tag: M.W=200-300

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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, A new synthetic method of this compound is introduced below., Formula: C6H8ClF3N4

General procedure: To the stirred reaction mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazine hydrochloride(11) (300 mg, 1.32 mmol), TEA (0.55 mL, 3.95 mmol)and toluene (10 mL), substituted cyanates 12(a-e)/isocyanates12(f-j) (1.32 mmol) were added at ambient temperature.The reaction mass was agitated at 75-80 C until thecompletion of the reaction that was monitored by TLC. Thereaction mass was allowed to cool at ambient temperatureand it was washed sequentially with 3% aqueous HCl(5.0 mL) and then water (5.0 mL). The organic fraction wasconcentrated under vacuum at 50-55 C to obtain crudeproduct. It was purified by column chromatography using10-50% of EtOAc:hexane mixture as a mobile phase.

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; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, 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. Product Details of 1196152-38-1

Example 44k (300 mg, 0.8 mmol), 2-Chloro-5-(trifluoromethyl)pyrimidine (199 mg, 1.09 mmol) and N,N-diisopropylethylamine (287 mul, 1.67 mmol) are dissolved in 4 ml of anhydrous DMSO and heated in a microwave reactor during 30 minutes at 150C. The crude is partitioned between EtOAc and water, the organic layer is dried over anhydrous Na2S04 then concentrated under reduced pressure to obtain 360 mg of the title product. HPLC-MS (Method 10): Rt = 3. MS (ES+): m/z = 505 [M+H]+ . The enantiomers are obtained by HPLC using a chiral stationary phase. Method for separation: HPLC apparatus type: Waters 600 Pump; column: Daicel Chiralpack AD-H, 5.0 muiotaeta, 250 mm x 20 mm; method: eluent hexane/ IPA 70:30; flow rate: 15 mL/min, Temperature: 25 C; UV Detection: 254 nm Example of separation by chiral HPLC: Submitted to separation: 665 mg of Example 1 prepared as described above; Obtained: 157 mg of enantiomer 1 (Exp. 2) and 40 mg of enantiomer 2 (Exp. 3). Example 26 is synthesized as described for example 1 starting from example 44k (70 mg, 0.18 mmol), 2-Bromo-5-(trifluoromethyl)pyrazine (60 mg, 0.26 mmol) instead of 2- Chloro-5-(trifluoromethyl)pyrimidine, N,N-diisopropylethylamine (60 mu, 0.35 mmol) and 1 ml of anhydrous DMSO. The reaction mixture is heated in a microwave reactor during 30 minutes at 150 C. After the work-up, the crude product is purified by preparative HPLC-MS to obtain the title compound (43 mg, 48 % yield). HPLC-MS (Method 10): Rt = 3. MS (ES+): m/z = 505 [M+H]+ .

The synthetic route of 2-Bromo-5-(trifluoromethyl)pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic 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.

To a solution containing 1.63 g (7.5 mmol) of 2-amino-5-bromopyrazine carboxylic acid in 25 mL of DMF was added 3.54 g (9.36 mmol) of HATU. The reaction mixture was allowed to stir for 15 minutes before the addition of 1.68 g (9.36 mmol) of 3-amino-4- morpholinopyridine and 2.5 mL (22.5 mmol) of N-methylmorpholine. The reaction was stirred for 16 h then quenched with a 10 mL of a saturated NaHCO, solution and extracted with EtOAc three times. The combined organic extracts were washed with brine and dried over Na2S04. Evaporation of the solvent and column chromatography (Si02; 10% CH3OH /DCM) provided Intermediate A as a yellow solid. 1H NMR (CD3OD) d 9.51 (s, 1H), 8.76 (s, 1H), 8.39 (d, J=5.4Hz, 1H), 7.94 (d, J=8. lHz, 2H), 7.39-7.27 (m, 8H), 5.10 (s, 2H), 3.81 (t, J=7.5Hz, 4H), 2.96 (t, J=7.5Hz, 4H). [M+H]+ = 568.1.

Statistics shows that 3-Amino-6-bromopyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 486424-37-7.

Reference:
Patent; SILVERBACK THERAPEUTICS, INC.; SMITH, Sean Wesley; COBURN, Craig Alan; BAUM, Peter Robert; DUBOSE, Robert Finley; (335 pag.)WO2019/227059; (2019); 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 1208082-91-0 as follows. HPLC of Formula: C7H5Br2N3

Preparation of Intermediate I-10. A mixture of Intermediate I-05 (1.75 g, 6.015 mmol), morpholine (0.526 mL, 6.015 mmol) and DCM (20 mL) was stirred at it for 16 h. Additional morpholine (0.526 mL, 6.015 mmol) was added and the mixture was stirred at it for 18 h more. Na2CO3 sat. aq. was added. The organic phase was separated, dried (Na2SO4), filtered and evaporated till dryness to obtain 1.8 g of intermediate I-10 (Y: quantitative). The resulting product was used in the next step without further purification.

According to the analysis of related databases, 1208082-91-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 87486-34-8, 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. 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A solution of r -butyl 4-(4-aminobenzoyi)piperazine- 1-carboxylate (2d, 1.7 g, 5.7 mmol, 1 equiv ), 3,5-dibromo-l-methylpyrazin-2(lH)-one (2e, 1.8 g, 6.8 mmol, 1.2 equiv.) and N,N-diisopropylethylamine (1.48 mL, 8.5 mmol, 1.5 equiv.) in N,N-dimethylacetamide (5 mL) was stirred in a sealed vial at 105 C for 30 h. The reaction was cooled to room temperature and EtOAc (20 mL) was then added. The solid precipitate was filtered and dried on high vacuum overnight to provide tert-butyi 4-(4-((6-bromo-4-methyl-3-oxo-3,4- dihydropyrazin-2~yl)amino)benzoy)piperazine-I -carboxylate 2f. The product was carried onto the next step without further purification.

The synthetic route of 3,5-Dibromo-1-methylpyrazin-2(1H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; WANG, Jinhua; DOBROVOLSKY, Dennis; (224 pag.)WO2019/148150; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1458-01-1, 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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 l) and NaOH (6 mol/l in water; 240 mL; 1.44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 mL). Water (200 mL) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60° C. C5H5ClN4O2 ESI Mass spectrum: m/z=189 [M+H]+; m/z=187 [M-H]-

The chemical industry reduces the impact on the environment during synthesis Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Boehringer Ingelheim International GmbH; HECKEL, Armin; KLEY, Joerg; US2015/11535; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 117719-17-2, 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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Preparation of Intermediate I-28. Intermediate I-02 (1.2 g, 4.7 mmol) and ethyl 2-chloroacetoacetate (2.3 g, 14.2 mmol) were suspended in EtOH (12 mL). The mixture was heated under microwave irradiation for 1 h at 150 C. After cooling down to room temperature, petroleum ether was added and the solid formed was filtered off. The filtrate was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (c-Hex/EtAOAc 8:2) to obtain a solid that was washed with petroleum ether to give the desired product I-28 (231 mg, Y: 33%).

The synthetic route of 5-Bromo-3-morpholinopyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, A new synthetic method of this compound is introduced below., category: Pyrazines

Example 1: 3-nitro-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)propan-1-one (NPTP) [Show Image] The title compound was prepared using the method described in WO 2008/040974. A mixture of 3-nitropropionic acid (20.0 g, 0.168 mol), 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (48.0 g, 0.21 mol) in acetonitrile (400 mL) is cooled to 0 C and 4-methylmorpholine (16.9 g, 0.168 mmol) is added, followed by N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (48.4 g, 0.25 mol) after 5 min. The resulting mixture is stirred at room temperature for 20 hours. The resulting mixture is concentrated to about 2/3 of it volume and ethyl acetate is added (750 mL). The resulting mixture is washed twice with water (200 + 100 mL), sat. aq. sodium hydrogencarbonate (200 mL), brine (200 mL) and dried with sodium sulfate. The resulting clear solution is concentrated under reduced volume and MTBE is added (100 mL). The precipitated white solid is filtered off, washed with MTBE (200 mL) and dried under reduced pressure to yield 38.8 g (79 % yield) of NTPT as white powder.

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; LEK Pharmaceuticals d.d.; EP2392575; (2011); 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 58139-04-1 as follows. Recommanded Product: 2-Iodo-3-methoxypyrazine

Intermediate 25 (0.15 g, 0.622 mmol) was dissolved in 1,4-dioxane (6 mL). 2-Iodo-3- methoxypyrazine (0.12 g, 0.508 mmol), cesium carbonate (0.405 g, 1.244 mmol, Iota, – bis(diphenylphosphino)ferrocene (0.052 g, 0.093 mmol) and tris(dibenzylideneacetone) dipalladium(0) (0.028 g, 0.031 mmol) were added. The reaction tube was sealed and the mixture was stirred at 160 C for 1 hour under microwave irradiation. After cooling, the reaction mixture was diluted with DCM and filtered over dicalite. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel; eluent: 7 M solution of ammonia in methanol/DCM 0/100 to 5/95). The desired fractions were collected and concentrated. This crude was further purified by preparative HPLC on (Chiralpal Diacel AS 20x250mm). Mobile phase (C02, MeOH with 0.2% iPrNH2) to yield compound 8 (0.010 g, 5% yield).

According to the analysis of related databases, 58139-04-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GIJSEN, Henricus, Jacobus, Maria; VAN BRANDT, Sven, Franciscus, Anna; WO2013/83556; (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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H8ClF3N4

General procedure: To the stirred reaction mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazine hydrochloride(11) (300 mg, 1.32 mmol), TEA (0.55 mL, 3.95 mmol)and toluene (10 mL), substituted cyanates 12(a-e)/isocyanates12(f-j) (1.32 mmol) were added at ambient temperature.The reaction mass was agitated at 75-80 C until thecompletion of the reaction that was monitored by TLC. Thereaction mass was allowed to cool at ambient temperatureand it was washed sequentially with 3% aqueous HCl(5.0 mL) and then water (5.0 mL). The organic fraction wasconcentrated under vacuum at 50-55 C to obtain crudeproduct. It was purified by column chromatography using10-50% of EtOAc:hexane mixture as a mobile phase.

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 762240-92-6.

Reference:
Article; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem