Tag: M.W=100-200

36070-80-1, Adding a certain compound to certain chemical reactions, such as: 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, belongs to Pyrazines 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 36070-80-1.

Step 1: 5-chloro-N-[(lS)-2,2,2-trifluoro-l-methylethyl]pyrazine-2-carboxamideN,N-Diisopropylethylamine (1.3 mL, 7.5 mmol) was added to a mixture of 5- chloropyrazine-2-carboxylic acid (0.40 g, 2.5 mmol), N,N,N’,N’-tetramethyl-0-(7- azabenzotriazol-l-yl)uronium hexafluorophosphate (1.0 g, 2.8 mmol) and (2S)-1,1,1- trifluoropropan-2-amine (0.28 g, 2.5 mmol) (Oakwood: Cat.No.44272) in methylene chloride (10 mL). The reaction mixture was stirred at room temperatureovernight. The reaction mixture was worked up with saturated aqueous NaHCC , and extracted with ethyl acetate (3x 20 mL). The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-15%) to afford the desired product (0.64 g, 73%). LCMS (M+H) +: m/z = 253.9/255.9.

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-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; YAO, Wenqing; BURNS, David M.; ZHUO, Jincong; WO2012/177606; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 113305-94-5

4G. Benzyl-(2-{4-[(Z)-3-(5-cyano-yrazin-2-ylamino)-3-methylsulfanyl-acryloyl]-3- methoxy-henyl}-ethyl)-carbamic acid tert-butyl esterA solution of 2-amino-5-cyanopyrazine (0.12 g, 0.92 mmol) was added in portions to a stirred slurry of NaH (60% in mineral oil) (0.040 g, 0.92 mmol) in THE (3 mL) at room temperature. The mixture was stirred for 30 minutes then benzyl-{2-[4-(3,3-bis- methylsulfanyl-acryloyl)-3-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester (0.30 g, 0.62 mmol) was added and the reaction mixture was then heated to 65C for 12hours. The solution was allowed to cool to room temperature then water (10 mL) was carefully added and the mixture extracted with EtOAc (3 x 20 mL). The combined organic extracts were washed with brine (10 mL), dried (Na2SO4) and evaporated under reduced pressure to leave a residue that was purified by column chromatography on neutral silica gel (60-120 mesh) using 15-30% EtOAc/hexanes asthe eluent to give the title compound (0.17 g, 49%).

The synthetic route of 113305-94-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONCOTHYREON INC.; BOYLE, Robert, George; WALKER, David, Winter; BOYCE, Richard, Justin; PETERSON, Scott; FAROUZ, Francine; VO, Cong, Hung; WO2015/120390; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-29-5, Name is 2-Amino-5-chloropyrazine, 33332-29-5, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, 5-chloropyrazin-2-amine (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

Statistics shows that 2-Amino-5-chloropyrazine is playing an increasingly important role. we look forward to future research findings about 33332-29-5.

Reference:
Article; Zitko, Jan; Mindlova, Al?b?ta; Vala?ek, Ond?ej; Jand’ourek, Ond?ej; Paterova, Pavla; Janou?ek, Ji?i; Kone?na, Klara; Dole?al, Martin; Molecules; vol. 23; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

27398-39-6, Name is 3-Chloropyrazine-2-carboxylic acid, 27398-39-6, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Step 4: 3-chloro-N-[[1 -r3-chloro-5-r2-(trifluoromethyl)cvclopropyll-2-Pyridyllcvclopropyllmethyllpyrazine-2-carboxamide (compound A.1 1 1 )147 mg [1 -[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine (step 3) was dissolved in 3 ml of dichloromethane and 0.142 ml triethylamine was added. After cooling to 0¡ãC, 193 mg 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine hydrochloride, 84 mg 3-chloropyrazine-2-carboxylic acid and 141 mg 1- hydroxybenzotriazole were added. The mixture was stirred overnight at ambient temperature. Then water was added. The layers were separated, the organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. Crude material was obtained as an orange oil, which was purified by flash chromatography on silica gel with heptane/ethyl acetate as a solvent. Thus, 161 mg of 3-chloro-N-[[1-[3-chloro-5-[2- (trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methyl]pyrazine-2-carboxamide was obtained as a yellow sticky solid. 1H-NMR (CDCI3): 8.42 ppm (d, 1 H), 8.38 ppm (d, 1 H), 8.18 ppm (s, 1 H), 7.78 ppm (s, 1 H, broad), 7.31 ppm (s, 1 H), 3.66 ppm (d, 1 H), 2.26 ppm (m, 1 H), 1 .78 ppm (m, 1 H), 1.57 ppm (m, 1 H), 1.39 ppm (m, 1 H), 1.18 ppm (m, 4H).

Statistics shows that 3-Chloropyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 27398-39-6.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; PITTERNA, Thomas; LOISELEUR, Olivier; WORTHINGTON, Paul, Anthony; O’SULLIVAN, Anthony, Cornelius; LUKSCH, Torsten; BOBOSIK, Vladimir; WO2013/64521; (2013); 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. 123-32-0, name is 2,5-Dimethylpyrazine, A new synthetic method of this compound is introduced below., 123-32-0

Preparation of 3,6-dimethyl-2- (3-chloro) benzoyl pyrazine, comprising the steps of:(1) 2,5-dimethyl pyrazine take 0.2mmol, 3- chloro-benzoyl formate 0.4mmol, silver phosphate 0.02mmol, potassium persulfate 0.4mmol, 1.4mL was added dichloromethane, 0.6mL distilled water after the mixture was made, and the mixture was placed in a reaction tube in 5mL, placed in an oil bath at 40 heated, the reaction 24h, cooled to room temperature to obtain a reaction solution;(2) The step (1) the resulting reaction mixture was directly concentrated to give a concentrate, the concentrate with ethyl acetate / petroleum ether = 1/2 (v / v) as the developing solvent, separation by thin layer chromatography to give 37mg target The product, 74% yield.

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; Henan Agricultural University; Wu Zhiyong; Zhao Mingqin; Li Yuan; (10 pag.)CN108101856; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

98-97-5, These common heterocyclic compound, 98-97-5, name is Pyrazine-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 stirring solution of 372 mg of pyrazine-2-carboxylic acid (3 mmol), 623 mg of (S)-methyl 2-amino-2-cyclohexylacetate (3 mmol), and 2.5 mL of N,N-diisopropyl ethylamine in 25 mL of anhydrous dichloromethane, was added 760 mg of 1,4-dimethyl-2-chloroimidazolium hydrochloride (4.5 mmol) in three portions. The resulting mixture was stirred at RT for additional 30 min, then concentrated under reduced pressure. The residue was re-dissolved into 80 mL of ethyl acetate, and washed with aqueous sodium bicarbonate, brine, and dried over anhydrous sodium sulfate. After concentration, the crude product was purified by flash column chromatography, eluting with heptane/ethyl acetate (v/v 2/1), giving 897 mg of yellowish oil as desired ester.

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 98-97-5.

Reference:
Patent; Avila Therapeutics, Inc.; US2010/41674; (2010); 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., 33332-25-1

Preparation of 5-Chloropyrazine-2-carboxylic acid To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added methyl 5-chloropyrazine-2-carboxylate (1.0 eq) and tetrahydrofuran (4.92 vols) under a nitrogen atmosphere. The reaction mixture was agitated until all the solid had dissolved, then filtered into a second flask. Water (8.65 vols) was added to the reaction mixture and the mixture agitated for approximately 15 minutes. Potassium carbonate (2.1 eq) was added to the reaction mixture and the mixture agitated for 16 hours at 20-25 C. Then 32% w/w hydrochloric acid (3.76 eq) was added over 3 hours in small portions, keeping the reaction temperature 20-25 C., to a pH end point of pH2.2. The resultant slurry was heated to approximately 35-40 C. and then distilled under vacuum at this temperature distilling approximately 5.3 vols, to a final volume of approximately 9.3 vols. The mixture was then cooled to 20-25 C. over at least 2 hours, agitated for 10 hours at this temperature and then filtered. The solid was washed with water (2.8 vols), and the wet product produced dried at 35 C. in a vacuum oven. The desired product was obtained as a solid (corrected yield 91%) 1H NMR delta (400 MHz CDCl3): 7.20 (1H, bs), 8.72 (1H, s), 9.21-9.21 (1H, m); m/z 157 (M-H)+.

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; AstraZeneca AB; US2010/210621; (2010); A1;,
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

875781-43-4, 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 875781-43-4 as follows.

Step 4: Synthesis of 2-Bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine.[0285] To a solution of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine (258 mg, 1.3 mmol) inacetone (5 ml) was added Af-iodosuccinimide (324 mg, 1.44 mmol) in one portion. Thereaction mixture was stirred at room temperature for 45 minutes. The resulting precipitatewas filtered off, washed with a minimal amount of acetone, and dried in vacuum to give thetitle compound as a light brown solid ^-NMR (500 MHz, d6-DMSO) ?12.81 (s br, 1H),8.40 (s, 1H), 8.19 (d, 3.0Hz, 1H). MS: m/z 323.8/325.8 [MH+].

According to the analysis of related databases, 875781-43-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2006/15124; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common heterocyclic compound, 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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. 23611-75-8.

Add methyl 6-chloropyrazine-2-carboxylate (20. 0 g, 116 mmol) in THF (1 00 mL) to methylmagnesium bromide (3.0 mol/L) in diethyl ether (120 g, 348 mmol, 3.0 mol/L) at 0 C and the mixture is stirred at this temperature for 2 h. The reaction is quenched with 1.0HCl solution (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic layers are washed with brine (100 mL), dried over anhydrous sodium sulfate, concentrated to afford a yellow oil. The yellow oil is purified by column chromatography on silica gel eluting with 0-30% EA in PE to afford title compound (3.80 g, 18.0%) as brown oil. LCMS (m/z): 5 172.8 [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 Methyl 6-chloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; MA, Tianwei; WU, Liang; ZHANG, Xuejun; (109 pag.)WO2019/41340; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem