Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, 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 36070-75-4, Recommanded Product: 5-Chloropyrazine-2-carbonitrile

Step 1: Synthesis of 5-(4-fluoro-lH-pyrazol-l-yl)pyrazine-2-carbonitrile. (0362) To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-lH-pyrazole (170 mg, 2.0 mmol) and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at 100 C for 4 hours, then cooled to 20 C, poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and purified by column chromatography (hexane: ethyl acetate = 5: 1) to give 5-(4-fluoro-lH- pyrazol-l-yl)pyrazine-2-carbonitrile (310 mg, 82%). The structure was confirmed by LC-MS.

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Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; KIM, Joseph, L.; WILSON, Kevin, J.; WILSON, Douglas; DIPIETRO, Lucian, V.; (84 pag.)WO2017/79140; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 54608-52-5, These common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, 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: To a vigorously stirred mixture of alpha-bromonitroalkane (0.50 mmol), heteroaryl hydrazine (0.60 mmol, 1.2 equiv), potassium iodide (1.0 mmol, 2.0 equiv) and potassium carbonate (1.0 mmol, 2.0 equiv) in 1,2-dimethoxyethane (5.0 mL) was added a solution of urea hydrogen peroxide in 1,2-dimethoxyethane/water (4:1) (0.50 M solution, 1.0 mL, 0.50 mmol, 1.0 equiv) over 2 h via syringe pump at r.t. After the addition was complete, the mixture was stirred for an additional 4 h. Aqueous sodium thiosulfate was then added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography to give pure fused triazole.

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tokumaru, Kazuyuki; Bera, Kalisankar; Johnston, Jeffrey N.; Synthesis; vol. 49; 20; (2017); p. 4670 – 4675;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 16298-03-6,Some common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, molecular formula is C6H7N3O2, 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 3a: methyl 3-amino-6-iodopyrazine-2-carboxylate 1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65 C for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65C for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10% sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88%) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid. LCMS (EI, m/z): (M+l) 280 1H NMR: deltaEta ppm (400 MHz, DMSO): 8.50 (1H, s, CHarom), 7.50 (2H, bs, NH2), 3.20 (3H, s, CH3).

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

Reference:
Patent; PIERRE FABRE MEDICAMENT; SOKOLOFF, Pierre; CACHOUX, Frederic; WO2014/16433; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6164-79-0, The chemical industry reduces the impact on the environment during synthesis 6164-79-0, name is Methyl 2-pyrazinecarboxylate, I believe this compound will play a more active role in future production and life.

Synthesis of pyrazin-2-ylmethanol:To a stirred solution of methyl pyrazine-2-carboxylate (0.5 g, 3.62 mmol) in H20 (10 mL) was added NaBH4 (685 g, 18.02 mmol) portion wise at 0 C, and the reaction mixture was allowed to warm to RT and stirred for 30 min under inert atmosphere. To this saturated K2C03 (10 mL) and EtOH (5 mL) was added and stirring was continued for another 1 h at RT. The progress of the reaction was monitored by TLC; the reaction mixture was extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to afford crude pyrazin-2-ylmethanol (0.3 g). LC-MS: 99.91%; 111.9 (M++l) (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 0.72 min. 0.1% TFA in water: ACN; 0.8 ml/min); TLC: 100% EtOAc (Rf: 0.2).

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, Methyl 2-pyrazinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4430-75-5, The chemical industry reduces the impact on the environment during synthesis 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

To 3-(chlorosulfonyl)benzoyl chloride (0.36 g 1.5 mmol) in anhydrous dichloromethane (50 mL) was added octahydro-lH-pyrido[l,2-alpha]pyrazine (0.21 g, 1.5 mmol) in dichloromethane (4 mL) slowly over 10 minutes at room temperature. Then sodium carbonate (0.32 g, 3 mmol) was added. The mixture was stirred at room temperature for 5 hours. Then 3 -(trifluoromethyl)aniline (2.9 g, 18 mmol) was added. The mixture was stirred at room temperature for 5 days, then sodium carbonate(0.32 g, 3 mmol) and methanol (5 mL) were added, the mixture was stirred for 20 minutes, then filtered, and concentrated. The residue was purified by chromatography on silica gel (methanol/ethyl acetate = 1 : 10) to give the titled compound: 1U NMR (400 MHz, DMSO-J6) delta ppm 1.00-1.27 (m, 3H), 1.42-2.10 (m, 7H), 2.70-3.40 (m, 4H), 4.25-4.40 (m, IH), 7.40 (m, 3H), 7.50 (m, IH), 7.70 (m, 3H), 7.85 (m, IH), 10.80 (br s, IH); MS (ESI) m/z 468 (M+H)+.

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, Octahydro-2H-pyrido[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; ZHANG, Qingwei; STEWART, Andrew, O.; XIA, Zhiren; WO2010/83264; (2010); 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. 56423-63-3, name is 2-Bromopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Bromopyrazine

Intermediates 2(R)-N-((l S,2S)-l-(3-bromopyrazin-2-yl)-2-(2,3-difluorophenyl)hex-5- enyl)-2-methylpropane-2-sulfinamide. In an oven-dried 250 mL round-bottomed flask was dissolved diisopropylamine (1.7 mL, 12 mmol) in tetrahydrofuran (40 mL) to give a colorless solution under nitrogen. After cooling to -30C, n-BuLi (4.3 mL, 11 mmol) was added, and the mixture was briefly warmed up to rt for 3 min. After cooling down to -78C, 2-bromopyrazine (0.98 mL, 10.7 mmol) was added dropwise via syringe. The resulting yellow solution was stirred at -78C for 5 min. (R,E)-N- ((S)-2-(2,3-difluorophenyl)hex-5-enylidene)-2-methylpropane-2-sulfinamide (2.089 g, 6.67 mmol) in 4 mL anhydrous tetrahydrofuran (plus 3 mL rinse) was added via canuula, and the mixture was stirred for 2 h at -75C. The reaction was quenched with saturated sodium bicarbonate solution and diluted with ethyl acetate. The layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, and concentrated to give a tan oil. Flash column chromatography up to 80% ethyl acetate/hexane afforded the desired product (1.964 g, 62%) as a dense tan oil: XH NMR (400 MHz, CHLOROFORM-d) delta ppm 8.33 (d, J=2.26 Hz, 1 H) 8.26 (d, J=2.26 Hz, 1 H) 6.99 – 7.22 (m, 3 H) 5.74 (d, J=6.53 Hz, 1 H) 5.18 (dd, J=9.29, 5.27 Hz, 1 H) 4.85 – 4.99 (m, 2 H) 4.30 (d, J=9.54 Hz, 1 H) 3.66 – 3.77 (m, 1 H) 2.17 (br. s., 1 H) 1.80 – 2.04 (m, 3 H) 1.05 (s, 9 H); 19F NMR (376 MHz, CHLOROFORM-d) delta ppm -138.41 (d, J=15.61 Hz, 1 F) -144.20 – – 143.20 (m, 1 F); 13C NMR (101 MHz, CHLOROFORM-d) delta ppm 155.19 (s, 1 C) 151.32 – 149.72 (dd, J=13.87 and 249.47 Hz, 1 C) 150.24 – 147.67 (dd, J=12.72 and 246.95 Hz, 1 C) 142.89 (s, 1 C) 141.44 (br. s., 1 C) 140.47 (s, 1 C) 136.93 (d, J=10.02 Hz, 1 C) 127.54 (d, J=10.79 Hz, 1 C) 124.12 – 124.96 (m, 1 C) 123.41 – 123.97 (m, 1 C) 115.23 – 1 15.83 (m, 1 C) 1 15.09 (s, 1 C) 59.93 – 60.56 (m, 1 C) 56.10 – 56.69 (m, 1 C) 40.72 – 41.81 (m, 1 C) 30.81 (s, 1 C) 30.34 (br. s., 1 C) 21.94 (q, J=6.17 Hz, 3 C).

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; DUBOWCHIK, Gene M.; MACOR, John E.; CHEN, Ling; WO2012/154354; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63286-28-2, The chemical industry reduces the impact on the environment during synthesis 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, I believe this compound will play a more active role in future production and life.

Reference Example 23-2 Preparation of N’-(3-chloropyrazin-2-yl)-2-ethylpiperidine-1-carbohydrazide racemate To a 100 mL eggplant flask were added 2-ethylpiperidine-1-carbonylchloride (509 mg) prepared in the Reference Example 23-3, diisopropylethylamine (1.11 g), acetonitrile (10 mL), and 2-chloro-3-hydrazinylpyrazine (947 mg) under argon gas flow at room temperature, and the resulting mixture was stirred at 80 C. for 1 hour. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography (hexane:ethyl acetate) using YAMAZEN medium pressure preparative (Silica L (40 g)), the fractions comprising the target compound (Rf value=0.70 (ethyl acetate)) were collected, and concentrated under reduced pressure to give the title compound (332 mg) (yield 36%) as a yellow foam. MS(CI) m/z: 284/286 [M+H]+

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, 2-Chloro-3-hydrazinylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; UBE INDUSTRIES, LTD.; NAKAJIMA, Tatsuo; HAYASHI, Norimitsu; ISHIZAWA, Kouhei; TSUZAKI, Yasunori; IWAMURA, Ryo; TSUBOIKE, Kazunari; US2019/185479; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 89123-58-0, 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. 89123-58-0, name is 5-Bromopyrazine-2,3-diamine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(b)Add Compound II (7.8 g, 41.3 mmol, 1 eq) to a 250 mL vial and add 80 mL of DMF (ie N,N-dimethylformamide) under constant stirring to dissolve Compound II and add the original Triethyl formate (7.34 g, 49.5 mmol, 1.2 eq) and 20 ml formic acid (about 1 drop/sec)Heating under reflux for 24 h under nitrogen protection(At this time, the TLC test is basically free of raw materials); the solvent is spun off, and methanol is dissolved.Purification by silica gel column chromatography gave 5 g of compound III.

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

Reference:
Patent; Suzhou Derivative Biological Technology Co., Ltd.; Liu Ke; (7 pag.)CN108707150; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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 875781-43-4, category: Pyrazines

Step 1-Preparation of 3,5-dimethyl-4-(5H-pyrrolo[2,3-b]pyrazin-2-yl)isoxazole (22): To 2-bromo-5H-pyrrolo[2,3-b]pyrazine (21, 1.36 g, 6.87 mmol) in acetonitrile (51 ml) was added 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (1.87 g, 8.39 mmol), 1M potassium carbonate in water (17 ml), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.2 g, 0.26 mmol) under nitrogen. The reaction was heated at 160 C. in a microwave for 20 minutes. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 0% to 60% ethyl acetate in hexane to give product 22 (1.11 8g, 76%).

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, 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Plexxikon Inc.; Shi, Songyuan; Spevak, Wayne; Zhang, Jiazhong; (84 pag.)US2016/75712; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 68774-77-6, 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 68774-77-6 as follows.

General procedure: A mixture of chloro compound (50 mg) and amine derivative (2 equiv.) in PEG 400 (2 mL) wasstirred at 120 C for 5 min. After completion the reaction was then cooled to room temperature. DCM and water were added and the phases were separated. The aqueous phase was extracted withDCM and the organic phase was dried and filtered. The removal of solvent gave the product as solid.

According to the analysis of related databases, 68774-77-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Campos, Joana F.; Loubidi, Mohammed; Scherrmann, Marie-Christine; Berteina-Raboin, Sabine; Molecules; vol. 23; 3; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem