Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 59303-10-5, name is 2-Chloro-5-methylpyrazine, 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 59303-10-5, Product Details of 59303-10-5

To a solution of rac- I -((2S,3R,4R)-4-amino-2-ethyl-3-methyl-6-morpholino-3,4-dihydroqu inolin1(2H)-yl)ethanone (for a preparation see Intermediate 73, 50 mg, 0.158 mmol) in 1,4-dioxane (1.5 ml) was added tris(dibenzylideneacetone)dipalladium(0) (28.8 mg, 0.032 mmol), Davephos (12.40mg, 0.032 mmol), sodium tert-butoxide (30.3 mg, 0.315 mmol) and 2-chloro-5-methylpyrazine (40.5 mg, 0.315 mmol). The reaction mixture was heated under microwave conditions, using initial normal absorption setting, to 120 C for 30 mm. The sample was diluted with ethyl acetate (5 mL) and loaded onto a celite cartridge (2.5 g). The cartridge was washed with further ethyl acetate (2×10 mL), and the combined fractions dried under a stream of nitrogen. The sample was dissolved in DMSO(2×1 mL) and purified by MDAP (HpH). The solvent was blown down under a stream of nitrogen to give the required product (14 mg) as a yellow gum. LCMS (2 mm HpH): Rt = 0.87 mi [MH] = 410.

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-5-methylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, 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 109838-85-9, name: (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

Step B – Preparation of Compound Int-15b Int-15bTo a solution of (2R)-(-)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (0.61 g, 4.36 mmol) in THF (8 mL) was added n-BuLi (2.5 M in hexane, 1.8 mL, 4.58 mmol) at -78 °C. After allowed to stir for 0.3 hours, Compound Int-15a (2.75 g, 6.98 mmol) in 2 mL of THF was added and the mixture was allowed to stir at the temperature for 4 hours. The reaction was quenched by saturated aqueous H4C1 solution and the organic layers were extracted with EtOAc. The combined organic solution was washed with brine solution, dried (Na2S04), and concentrated in vacuo. The residue obtained was purified using ISCO 40 g column (gradient from 0percent to 2.5percent ether in hexane) to provide Compound Int-15b, 783 mg (44percent). 1H MR (CDC13) delta 4.05 (m, 1H), 3.96 (t, J= 3.4 Hz, 1H), 3.72 (s, 3H), 3.71 (s, 3H), 3.49 (dd, 7= 2,8, 0.4 Hz, 1H), 3.26 (dd, 7= 6, 9.4 Hz, 1H), 2.30 (m, 1H), 1.96 (m, 1H), 1.60 (m, 2H), 1.37-1.17 (m, 3H), 1.08 (d, 7= 6.9 Hz, 3H), 0.99-0.86 (m, 2H), 0.72 (d, 7= 6.6 Hz, 3H), 0.49 (dd, 7= 11.0, 14.4 Hz, 1H), 0.35 (dd, 7= 11.0, 14.2 Hz, 1H), 0.16 (s, 6H).

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; MERCK SHARP & DOHME CORP.; DWYER, Michael P; KEERTIKAR, Kartik M; COBURN, Craig A; WU, Hao; HU, Bin; ZHONG, Bin; ZHANG, Chengren; DAN, Zhigang; TONG, Ling; YU, Wensheng; WO2012/41227; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 59303-10-5, 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 59303-10-5 as follows.

A mixture of 2-chloro-5-methylpyrazine (300 mg, 1.6 mmol), (R)-tert-butyl 3-aminopyrrolidine-l- carboxylate (206 mg, 1.6 mmol), BINAP (199 mg, 0.3 mmol), Pd2(dba)3 (73 mg, 0.08 mmol) and t- BuONa (307 mg, 3.2 mmol) in toluene (10 mL) was stirred at 80C under N2 for 3 hours. The mixture was cooled to RT and concentrated. The residue was purified by reverse phase chromatography to afford (R)-tert-butyl 3-((5-methylpyrazin-2-yl)amino)pyrrolidine-l-carboxylate (240 mg, 54%) as yellow oil. [M+H] Calc?d for Ci4H22N402, 279.1; Found, 279.1.

According to the analysis of related databases, 59303-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); 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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

To a solution of (R)-2-isopropyl-3, 6-dimethoxy-2, 5-dihydropyrazine (500 mg, 2.72 mmol) and bis(chloromethyl) dimethylsilane (636 mg, 4.08 mmol) in THF (10 mL) under N2atmosphere in a dry ice/acetone bath was slowly n-BuLi (1.6 M in hexane, 2 mL, 3.2 mmol) via an injection syringe. After addition, the reaction was stirred at room temperature overnight. The reaction mixture was cooled to 0° C. and quenched by dropwise addition of water. The resulting mixture was extracted with EtOAc. The organic layer was washed by brine, dried over anhydrous Na2SO4and concentrated. The obtained crude product was purified by column chromatography on silica gel eluted with PE/EtOAc (100:1 to 30:1) to give the title compound (640 mg, 77.5percent yield); LC/MS (ESI) m/z: 305 [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; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 89123-58-0, 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. 89123-58-0 name is 5-Bromopyrazine-2,3-diamine, 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.

Example 52A 5-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrazine-2,3-diamine Under argon, 425 mg (1.20 mmol) of the compound from Example 33A were initially charged in 1,4-dioxane (11 ml), and the reaction mixture was purged with argon for 10 min. Thereafter, 0.91 ml (1.80 mmol) of hexabutylditin and 250 mg (1.32 mmol) of 2,3-diamino-5-bromopyrazine were added. Subsequently, 422 mg (0.60 mmol) of bis(triphenylphosphine)palladium(II) chloride were added and the reaction mixture was heated to reflux overnight. Thereafter, the mixture was cooled to RT and filtered through Celite, and the filtrate was concentrated. The residue was admixed with methanol, and the solids were filtered off and discarded. The filtrate was taken up in methanol-dichloromethane, absorbed onto diatomaceous earth and purified on silica gel (eluent: cyclohexane-ethyl acetate 2:1, 1:1). This gave 151 mg (31% purity, 11% of theory) of the title compound. The crude product was converted further without further purification. LC-MS (method 3): Rt=0.91 min MS (ESIpos): m/z=336 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromopyrazine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; Baerfacker, Lars; Weigand, Stefan; US2014/148433; (2014); 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H9N3

Example 32 (5,6-Dihydro-8H-imidazo[1,2-a]pyrazin-7-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone A mixture of sodium 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylate (0.3 g) and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine (0.24 g). HBTu (0.4 g), DIEA (1 mL), THF (3 mL) and DMA (3 mL) was stirred at room temperature for three hours. The reaction mixture was then partitioned between EtOAc and water, the organic layer washed with saturated NaHCO3 and water, dried over Na2SO4 and concentrated in vacuo. The residue was purified via prep. TLC (10% MeOH/DCM) to give 56 mg of (5,6-dihydro-8H-imidazo[1,2-a]pyrazin-7-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone. MS (M+H)=578.

According to the analysis of related databases, 91476-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gong, Leyi; Tan, Yun-Chou; US2011/301170; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 55557-52-3,Some common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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 13.1 (+-)-3-[(6R,8aS)[[(3-chlorophenyl)ethynyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl] pyrazine-2-carbonitrile A mixture of (+-)-(6R,8aS)-6-[(3-chlorophenyl)ethynyl]octahydropyrrolo[1,2-a]pyrazine (40 mg, 0.15 mmol), 2-chloro-3-cyanopyrazine(30 mg, 0.22 mmol), Et3N (0.1 mL) and THF (1.5 mL) was stirred at 80 C. for 4 h. The resulting mixture was concentrated and purified on silica gel column to provide product (44 mg, 81%). 1H NMR (300 MHz, CDCl3): delta (ppm) 1.62 (m, 1H), 1.85-2.25 (m, 5H), 3.02 (dd, 1H), 3.24-3.48 (m, 3H), 4.61 (dt, 2H), 7.29 (m, 3H), 7.45 (s, 1H), 8.02 (d, 1H), 8.27 (d, 1H).

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

Reference:
Patent; AstraZeneca AB; NPS PHARMACEUTICALS; US2007/37817; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 21279-62-9, name is 3-Chloropyrazine-2-carboxamide, 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. Recommanded Product: 3-Chloropyrazine-2-carboxamide

General procedure: The starting compound (1.27 mmol) was treated with 18 aliphatic amines, alicyclic amines or saturated heterocycles containing at least one nitrogen atom (2.54 mmol). Four reactions were completed by conventional heating methods. The conditions were 110 C, toluene as a solvent and pyridine (1.27 mmol) as a base. The reaction time was set to one hour. Then the reactions were completed using the microwave reactor with focused field and conditions used for syntheses were 140 C, 30 min,120 W, methanol used as a solvent and pyridine (1.27 mmol) as a base. They were set experimentally with respect to prior experience. The progress of reaction was monitored with TLC in system hexane/ethyl acetate (1:1). Then the mixture was separated by flash column chromatograph using gradient elution. Mobile phases were hexane and ethyl acetate again.

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

Reference:
Article; Jandourek, Ondrej; Dolezal, Martin; Kunes, Jiri; Kubicek, Vladimir; Paterova, Pavla; Pesko, Matus; Buchta, Vladimir; Kralova, Katarina; Zitko, Jan; Molecules; vol. 19; 7; (2014); p. 9318 – 9338;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 5521-55-1, A common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

5-Methyl-pyrazine-2-carboxylic acid (691 mg, 5 mmol) was stirred in toluene (15 mL) and treated with TEA (765 mL, 5.5 mmol) followed by diphenylphosphoryl azide (1.0 mL, 5.0 mmol). The resulting solution was stirred for 30 min, then used directly.A solution of 5-methyl-pyrazine-2-carbonyl azide (1.0 mmol) in toluene was heated at 900C for 10 min. The reaction flask was removed from the heating bath and the brown solution was treated with 2- (1,4- dimethyl-piperazin-2-ylmethoxy) -5-methyl-phenylamine EPO (0.25 g, 1.0 iranol) . The flask was returned to the heating bath and heated at 40C for 4 h. The mixture was allowed to cool, then filtered to give the product as a tan powder. 1H-NMR (400 MHz, CDCl3) delta 10.90 (s, 1, H), 8.4 (s, 1, H), 8.2 (m, 3, H), 6.8 (m, 2, H), 4.2 (dd, 1, H), 3.9 (t, 1, H),.3.1 (d, 1, H), 2.8 (br d, 1, H), 2.6 (m, 2, H), 2.5 (s, 3, H), 2.4 (m, 1, H), 2.4 (s, 3, H), 2.3 (S, 3, H), 2.25 (m, 1, H), 2.2 (s, 3, H), 2.1 (m, 1, H). LRMS (esi, positive) m/e 385.30 (M+l) .

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICOS CORPORATION; WO2006/105262; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 36070-80-1,Some common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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 of 5-chloropyrazine-2-carboxylic acid (3 g, 18.9 mmol) in dichloromethane (60 mL) was added oxalyl dichloride (2.52 g, 1.7 mL, 19.9 mmol) dropwise at 0C. Then to the mixture was added 2 drops of DMF and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was concentrated in vacuo to give 5- chloropyrazine-2-carbonyl chloride (3.4 g, 100%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloropyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; SHEN, Hong; TAN, Xuefei; WU, Jun; CHEN, Dongdong; LI, Chao; WANG, Li; (156 pag.)WO2020/53249; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem