Pyrazines

Reference of 6270-63-9, 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. 6270-63-9, name is Pyrazin-2(1H)-one belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A solution of N-((3-chloro-lH-indol-5-yl)methyl)-5-(4-(chloromethyl)benzyl)nicotinamide (90 mg, 0.21 mmol, 1.0 eq), pyrazin-2(lH)-one (41 mg, 0.42 mmol, 2.0 eq) and K2C03 (58 mg, 0.42 mmol, 2.0 eq) in MeCN (10 mL) was stirred at 80 C for 2 h and allowed to cool. The mixture was concentrated. The residue was purified by flash chromatography (MeCN/l hO = 1/2 to 19/1) to afford N-((3-chloro-lH-indol-5- yl)methyl)-5-(4-((2-oxopyrazin-l(2H)-yl)methyl)benzyl)nicotinamide as a white solid (6.3 mg, 6%). LRMS (M+H+) m/z calculated 484.1, found 484.1. NMR (DMSO-ifc, 400 MHz) delta 8.72 (s, 1 H), 8.44 (s, 1 H), 7.97 (s, 1 H), 7.95 (d, 1 H), 7.47 (d, 1 H), 7.40 (s, 1 H), 7.26-7.20 (m, 4 H), 7.16-7.10 (m, 3 H), 7.10-7.08 (m, 1 H), 5.00 (s, 2 H), 4.55 (s, 2 H), 3.96 (s, 2 H).

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

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, molecular formula is C6H3BrClN3, 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. SDS of cas: 143591-61-1

[00274] 3-(Trifluoromethyl)phenol (1.57 mL, 12.95 mmol) was added to a suspension of sodium hydride (706 mg, 17.65 mmol – 60% in mineral oil) in anhydrous DMF (30 mL) and the resulting mixture was stirred for 40 minutes. A solution of 3-bromo-8-chloroimidazo[l,2- ajpyrazine (2.731 g, 11.75 mmol) in anhydrous DMF (30 mL) was added to the reaction mixture and stirred overnight at room temperature. The reaction mixture was diluted with water and the resulting precipitate was filtered off and washed with water and then hexane to give 3-bromo-8-(3-(trifluoromethyl)phenoxy)imidazo[l,2-a]pyrazine (3.4g, 81%) as a white solid. LCMS MH+ 359.8. 1H NMR (d6-DMSO): 8.20 (IH, d, J 4.7), 7.96 (IH, s), 7.64-7.77 (4H, m), 7.52 (IH, d, J4.7).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 143591-61-1, its application will become more common.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
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Pyrazine | C4H4N2 – PubChem

Reference of 91476-80-1, These common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]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.

(1855) [00533] To a solution of 2-(4-bromophenethyl)isoindoline-l,3-dione (prepared according to the procedure described in Francis et al : Journal of Medicinal Chemistry (1991), 34(8), 2570- 2579; 0.2 M in anhydrous 1,4-dioxane; 150 muEpsilon, 30 mumol), was added 5,6,7,8- tetrah droimidazo[ 1 ,2- Jpyrazine (0,2 M in anhydrous 1 ,4-dioxane; 180 muTau, 36 muetaiotaomicron), RuPhos solution (0.02 M in anhydrous 1,4-dioxane/EtOAc; 75 uL, 1.5 mumo), RuPhos-Pd 2nd generation catalyst (0,02 M in anhydrous 1,4-dioxane, 75 mu., 1 ,5 muetaiotaomicron) and sodium fert-butoxide (2 M in THF; 150 mu^, 300 muthetaIota). The resulting mixture was heated at 100 C overnight. The reaction mixture was cooled to RT and used directly in Step 2 without further workup or i solation.

Statistics shows that 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 91476-80-1.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
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Pyrazine | C4H4N2 – PubChem

54608-52-5, name is 2-Hydrazinopyrazine, 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. Formula: C4H6N4

2) 6.0 g (55 mmol) of 2-hydrazinopyrazine was added250 mL of three-necked flask,Ice water cooled to 0 C,Under the magnetic stirring, 28.6 g was slowly added dropwise(136 mmol) of trifluoroacetic anhydride,Then rose to room temperature for 2 hours,Add 35 ml of diluted polyphosphoric acid(Diluted 10 grams of water per 100 grams of polyphosphoric acid)Heated to 80 C for 10 hours,After cooling to room temperature,To the residue was added 30 ml of ice water,Slowly drop the sodium hydroxide solution to adjust the pH value of 7-8,Ethyl acetate extraction,Combined organic layer,The organic phase is saturatedSodium chloride aqueous solution,Dried over anhydrous sodium sulfate,Condensed organic layer,To give 6.7 g of a pale yellow solid,Yield 65.1%.

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

Reference:
Patent; Nankai University; Wang, Baolei; Li, Zhengming; Zhang, Yan; (13 pag.)CN106749262; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

At room temperature,(3-(Aminomethyl)cyclobutyl)methyl benzoate (0.3 g, 5 mmol)And triethylamine (0.2 mL, 12 mmol)Add to 3-chloropyrazine-2-carbonitrile (0.5 g, 6 mmol) in THF (10 mL)The reaction solution was reacted at 25 C for two hours.After the reaction is completed,Concentrated under reduced pressure,The residue was purified by silica gel column chromatography (eluent: EtOAc (V/V) = 5/1)The title compound (0.32 g, 54%)

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Liu Xinchang; Tang Changhua; Zhang Jiancun; Zhang Yingjun; (30 pag.)CN104402833; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 110223-15-9, A common heterocyclic compound, 110223-15-9, name is 2-Amino-3-benzyloxypyrazine, molecular formula is C11H11N3O, 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.

2-Bromo-3-oxo-butyric acid ethyl ester (15.6 g, 74.6 mmol) was added to a solution of 2-amino-3-benzyloxypyrazine (Compound m in Scheme 1, 5 g, 24.9 mmol) in ethanol (20 mL). The reaction mixture was refluxed for 5 h. The reaction mixture was allowed to cool to r. t. and an off- white coloured solid precipitated out. The solid was collected and washed with ice-cold ethanol to give a white solid (1.08 g, 66%). 1H-NMR (DMSO-d6) No. 11.6 (br s, 1H), 7.97 (d, J5.7 Hz, 1H), 7.00 (t, J 5. 8-Hz, 1H), 4.35 (q, J 7.1 Hz, 2H), 2.52 (s, 3H), 1.34 (t, J 7.1 Hz, 3H); MS (ESI) 222.0 ([M+H])

The synthetic route of 110223-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CARDIOME PHARMA CORPORATION; WO2005/34837; (2005); A2;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 1458-18-0

To a stirred mixture of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (600 mg, 2.702 nMol, 1 equiv) and phenylboronic acid (336.09 mg, 2.756 nMol, 1.02 equiv) in dioxane (20 mL) were added K 3PO 4 (1147.23 mg, 5.405 nMol, 2 equiv) and Pd (dppf) Cl 2 (395.46 mg, 0.540 nMol, 0.2 equiv) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 3 h at 70 under nitrogen atmosphere. The resulting mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (PE/EtOAc 1: 1) to afford methyl 3-amino-6-chloro-5-phenylpyrazine-2-carboxylate (400 mg, 56.14%) as a yellow solid. LCMS: m/z (ESI) , [M+H] + = 264.3. 1H NMR (400 MHz, DMSO-d 6) delta 3.89 (3H, s) , 7.53 (3H, dd) , 7.61 (2H, s) , 7.71 -7.78 (2H, m)

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Formula: C6H3Br2N3

To a solution of 6,8-dibromoimidazo[1,2-a]pyrazine (0.50 g, 1.8 mmol) (Combi-Blocks, OR-7964) in DMF (12 mL) was added N-iodosuccinimide (0.45 g, 2.0 mmol). The reaction mixture was then heated at 60 C. for 15.5 h. The reaction mixture was concentrated in vacuo. The resulting solid was taken up into DCM. The organic layer was washed sequentially with water and sat. Na2S2O3 (aq). The organic layer was then dried over Na2SO4, filtered, and concentrated to afford the title compound as a light yellow solid (0.64 g, 88%). LCMS for C6H3Br2IN3 (M+H)+: calculated m/z=401.8, 403.8, 405.8; found 401.8, 403.7, 405.6.

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; Incyte Corporation; Buesking, Andrew W.; Sparks, Richard B.; Combs, Andrew P.; Douty, Brent; Falahatpisheh, Nikoo; Shao, Lixin; Shepard, Stacey; Yue, Eddy W.; (269 pag.)US2018/9816; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5780-66-5,Some common heterocyclic compound, 5780-66-5, name is Pyrazine-2-carbaldehyde, molecular formula is C5H4N2O, 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.

Method 54; Pvrazine-2-carboxaldehyde oxime A IN solution of lithium aluminium hydride in THF (73. 8ml, 73.8mmol) was added to a suspension of methyl pyrazine-2-carboxylate (20g, 145mmol) in anhydrous THF (300. 0ml) at-78°C keeping the reaction temperature below-72°C. On completion of addition the reaction mixture was left to stir at-78°C for a further 20 minutes and then quenched with glacial acetic acid (20. 0ml). The resulting mixture was warmed to room temperature and the volatiles removed by evaporation. The residue was dissolved in 3N hydrochloric acid (116ml) and extracted with DCM. The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution and the solvent evaporated. The residue was purified by chromatography on silica gel eluting with DCM/diethylether (100: 0 then 80: 20 and then 0: 100) to give pyrazine-2-carboxaldehyde (15.67g, 100percent). This was immediately dissolved in chloroform (200ml) cooled to 0°C and hydroxylamine mono-hydrochloride (11. 02g, 159. 5mmol) and triethylamine (24. 2ml, 117. 4mmol) were added. The reaction mixture was then stirred at ambient temperature for 0.5 hour, and the solvent removed by evaporation. The residue suspended in diethylether (500ml) and the insolubles removed by filtration. The filtrate was evaporated and the residue purified by chromatography eluting with DCM/diethylether (100: 0 then 80: 20 and then 0: 100) to give the title compound (5. 5g, 31percent) as a solid. NMR (DMSO-d6) : 8.15 (s, 1H), 8.62 (dd, 2H), 8. 99 (s, 1H).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/40159; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 14508-49-7, 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. 14508-49-7, name is 2-Chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2-Aminoethanethiol hydrochloride (1.1-1.2 equiv) was suspended in dry HMPA (1-4 mL). NaH (dry, 95%) (2.4-2.6 equiv) was added portion-wise over 10-20 min while the reaction mixture was cooled in an ice-cold water bath under a nitrogen atmosphere. The mixture was stirred for 10 min at ambient temperature before portion-wise addition of the desired halogenated heterocycle (1.22-17.5 mmol, 1 equiv) over 10 min. The reaction mixture was stirred at ambient temperature for 2 h-2 days. Water was added slowly to quench the reaction then the aqueous layer was extracted with CH2Cl2, and the combined organic extract dried (MgSO4), filtered and solvent removed in vacuo to give the crude product. TLC on silica using CH2Cl2/MeOH/NH3 in MeOH, 9:0.8:0.2 showed the products with Rf values in the range 0.15-0.20.

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

Reference:
Article; Mountford, Simon J.; Campi, Eva M.; Robinson, Andrea J.; Hearn, Milton T.W.; Tetrahedron; vol. 67; 2; (2011); p. 471 – 485;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem