Month: April 2021

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. 121246-96-6, name is 3-Chloropyrazine-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Chloropyrazine-2-carbaldehyde

PREPARATION 14; EPO 4-Methyl-3,4,5,6-tetrahvdro-2H-?,2’lbipyrazinyl-3′-carbaldehvde;.S-Chloro-pyrazine^-carb-aldehyde (Turck, et al., Synthesis 1988, 881-4) (6.01 g, -40 mmol), N-methylpiperazine (6.6 mL, 59.4 mmol) and K2CO3 (8.3g, 60.0 mmol) were refluxed for 1h in dioxane (250 mL). After cooling, the mixture was filtered and concentrated to an orange oil. This was dissolved in EtOAc (500 mL) and washed with water (4×150 mL) and brine, dried (MgSO4) and concentrated. Chromatography with 5% MeOH/ CH2CI2 gave 3.34 g (40%) of PP14 as a dark red oil : NMR (CDCI3) 9.94 (s, 1 H), 8.18 (d, J= 2.1 Hz, 1 H), 8.08 (d, J = 2.1 Hz, 1 H), 3.59 (t, J= 5.2 Hz, 4H), 2.53 (t, J = 5.0 Hz, 4H), 2.32 (s, 3H).

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 121246-96-6.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2006/48727; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 2423-65-6, name is Pyrazine 1-oxide, 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. name: Pyrazine 1-oxide

General Procedure 2:; Palladium-Catalyzed Direct Arylation with Aryl Chlorides and Bromides.; To a dried flask was added the diazine N-oxide (1.0 to 3.0 equiv.), K2CO3 (2.0 equiv.), Pd(OAc)2 (5 mol %) and HP(t-Bu)3BF4 (15 mol %). If the arylhalide is a solid, it is added at this point (1.0 equiv.). The flask and its contents were then purged under nitrogen for 10 minutes. If the aryl halide is a liquid, it is added via syringe after purging, followed by the addition of degassed dioxane (to produce a reaction concentration of 0.3 M relative to the halide). The reaction mixture was then heated at 110 C. until the reaction was complete, after which the volatiles were removed under reduced pressure and the residue was purified via silica gel column chromatography.; 2-p-Tolylpyrazine N-oxide (81) Synthesised according to general procedure 2 employing the corresponding aryl bromide and chloride or 60 with the corresponding aryl iodide. Purification via silica gel column chromatography using 100% DCM then a mixture of 20% Acetone/DCM gave a white solid, 72% (from the bromide), 75% (from the chloride) and 77% (from the iodide). 1H NMR (300 MHz, CDCl3, 293K, TMS): delta 8.63 (1H, s), 8.37 (1H, s), 8.20 (1H, s), 7.72 (2H, d, J=8.1 Hz), 7.33 (2H, d, J=7.8 Hz), 2.43 (3H, s). 13C NMR (75 MHz, CDCl3, 293K, TMS): 148.2, 145.2, 144.6, 140.8, 134.2, 129.8, 129.0, 125.9, 21.5.

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

Reference:
Patent; University of Ottawa; US2008/132698; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 41270-66-0, A common heterocyclic compound, 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, molecular formula is C16H11ClN2, 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.

30 g of 2-chloro-5,6-diphenylpyrazin and 131.22 g (0.3 mol) of 4-isopropylamino-1-butanol were added into a 500 mL flask, the mixture was heated to 190 C. and reacted at this temperature for 10 hours, cooled, samples were taken for testing, HPLC purity of the product was 63.5%. The reaction solution was poured into 1 L of ice water, the mixture was extracted with ether 200 mL¡Á3, the organic phases were combined and the solvent was concentrated to dryness, then the residue was purified by column chromatography, and 22.96 g of 4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]-1-butanol was obtained, HPLC purity was 97.2%, the molar yield was 56%. (0083) 1H-NMR data: 1H-NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 7.46 (d, 2H, J=7.6 Hz), 7.36 (d, 2H, J=7.2 Hz), 7.28-7.22 (m, 6H), 4.80-4.78 (m, 1H), 3.71 (t, 2H, J=6.4 Hz), 3.45 (t, 2H, J=7.6 Hz), 1.77-1.74 (m, 2H), 1.66-1.64 (m, 2H), 1.29 (d, 6H, J=6.8 Hz).

The synthetic route of 41270-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Seasons Biotechnology (Taizhou) Co., Ltd.; TANG, Fanghui; MA, Chi; JIA, Qiang; (11 pag.)US2018/29998; (2018); 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5-iodopyrazine

Step 1: N-1-(5-Iodo-pyrazin-2-yl)-2-methyl-propane-1,2-diamine To a solution of 2-bromo-5-iodopyrazine (CAS 622392-04-5) (250 mg, 878 mmol) in 0.7 ml of pyridine, was added 2-methylpropane-1,2-diamine (116 mg, 138 mul, 1.32 mmol, 1.5 equiv.) at room temperature. The colorless solution was stirred for 16 hours at 100 C. The reaction mixture was cooled and concentrated in vacuo. The crude material was used directly in the next step.

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; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, 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. Recommanded Product: 33332-25-1

A mixture of 4-aminotetrahydropyran (500 mg, 4.94 mmol) and methyl 2-chloropyrazine-5-carboxylate (770 mg, 4.46 mmol) in DMF (5 mL) containing N,N-diisopropylethylamine (1.0 mL, 5.7 mmol) was stirred at 55 C. for 17 hrs. The reaction mixture was concentrated and the residue was partitioned between ether (25 mL) and hydrochloric acid (1N, 25 mL). The aqueous layer was further extracted with ether (25 mL). The resulting aqueous layer was first treated with sodium chloride (10 g) and then extracted with methylene chloride (3¡Á50 mL). The organic layer was washed with brine and dried over sodium sulfate. Solvents were evaporated to give an oil which slowly crystallized as methyl 2-(N-tetrahydropyran-4-yl)-aminopyrazine-5-carboxylate (900 mg, 85%). MS calcd for C11H15N3O3 (m/e) 237, obsd 238.1 (M+H).

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolin, David Robert; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Hamilton, Matthew Michael; Li, Shiming; McDermott, Lee Apostle; Qian, Yimin; Yun, Weiya; US2007/123504; (2007); 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 5521-58-4 as follows. Recommanded Product: 5-Methylpyrazin-2-amine

Oxalyl chloride (1.9 mL, 22.2 mmol) and DMF (1 drop) were added to a solution of 3- [(phenylmethyl)oxy]-5-[(3^-tetrahydrofuran-3-yloxy]benzoic acid (5.8 g, 18.5 mmol) in DCM (100 mL) and the mixture stirred at RT for 16 hours. The mixture was evaporated in vacuo to a residue which was redissolved in DCM (25 mL) and added to a stirred mixture of 2-amino-5-methylpyrazine (2.22 g, 20.35 mmol) and pyridine (1.81 mL, 22.2 mmol) in DCM (100 mL) at 50C – 1O0C. The mixture was stirred at RT for 18 hours, the DCM evaporated in vacuo to give a residue which was partitioned between water (50 mL) and ethyl acetate (125 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 60% ethyl acetate in isohexane, to give the desired material (5.1 g). 1H NMR delta (CDCl3): 2.1 – 2.2 (m, 2H), 2.5 (s, 3H), 3.8 – 3.95 (m, 4H), 4.9 (m, IH), 5.0 (s, 2H), 6.6 (s, IH), 6.95 (s, IH), 7.05 (s, IH), 7.35 (m, 5H), 8.05 (s, IH), 8.3 (s, IH), 9.5 (s, IH); m/z 406 (M+H)+.

According to the analysis of related databases, 5521-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125972; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, 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. Computed Properties of C4H3ClN2

In a sealed tube, 2-chloropyrazine (1.0 g, 8.7 mmol, 1 equiv) was heated withethanolic methylamine (33% w/w; 4.0 g, 43.6 mmol, 5 equiv) at 95 C for 1 h.Solvent and excess of methylamine were then removed under reduced pressure. Theresidue was then dissolved in dichloromethane and washed three times with water.The organic phase was then evaporated under reduced pressure and the crude productwas further purified by flash chromatography on silica gel (EtOAc/Et2O= 1:6 to 1:4).The product S2 was obtained as a colorless oil (0.73 g, 6.7 mmol, 77% yield), whichsolidified as a light brown solid. The spectra are in agreement with the literaturereport.1

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

Reference:
Article; Huang, Qi; Qin, Ling; Zard, Samir Z.; Tetrahedron; vol. 74; 40; (2018); p. 5804 – 5817;,
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. 19847-12-2, name is Pyrazinecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Pyrazinecarbonitrile

To a solution of pyrazine-2-carbonitrile (1.0 g, 9.52 mmol) in methanol (20 mL) was addedNaOCH3 (0.10 g, 1.90 mmol). The resulting mixture was heated with stirring at rt for 12 hrs. Tothe reaction mixture was added NH4C1 (0.51 g, 9.52 mmol). After being heated under reflux for 3 hrs, the resulting reaction mixture was concentrated in vacuo. The residue was suspended in ethanol (30 mL). The suspension was heated under reflux for 1 hr, then cooled to rt and filtered. The filtrate was concentrated in vacuo to give pyrazine-2-carboxamidine hydrochloride (1.2 g),which was used in the next step without further purification.

According to the analysis of related databases, 19847-12-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 136927-64-5,Some common heterocyclic compound, 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, molecular formula is C7H5ClN2, 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.

Compound C21 (500 mg, 2.22 mmol), 1-chloropyrrolo[1,2-a]pyrazine (339 mg, 2.22 mmol), cesium carbonate (796 mg, 2.44 mmol), and palladium(ll) acetate (53 mg,0.22 mmol) were combined in 1,4-dioxane (15 mL), and the solution was degassed with nitrogen for 15 minutes. Di-tert-butyl[3,4, 5,6-tetramethyl-2?, 4?,6?-tri(propan-2-yl) bi phenyl2-yl]phosphane (214 mg, 0.444 mmol) was added to the reaction mixture, which wasthen degassed for an additional 2 minutes. The reaction mixture was heated to 100 00 in a microwave reactor for 6 hours, whereupon it was cooled to room temperature andfiltered through diatomaceous earth. The filter cake was washed with ethyl acetate, andthe combined filtrates were concentrated in vacuo. Silica gel chromatography (Gradient:20% to 80% ethyl acetate in heptane) was followed by three triturations with heptane;the resulting material was purified again using silica gel chromatography (Gradient:50% to 70% ethyl acetate in heptane) to provide the product as a pale yellow solid.Yield: 361 mg, 1.06 mmol, 48%. LCMS m/z 342.1 [M+H]. 1H NMR (400 MHz, ODd3) oe9.05 (5, 1H), 7.82 (d, J=2.5 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 7.68-7.66 (m, 1H), 7.50(dd, J=2.5, 1.4 Hz, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.09 (d, J=4.9 Hz, 1H), 7.01-6.98 (m,1H), 6.89 (dd, J=2.5, 4.1 Hz, 1H), 2.36 (5, 6H).

The synthetic route of 136927-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 939412-86-9, name: (3-Chloropyrazin-2-yl)methanamine hydrochloride

(g) N-((3-chloropyrazin-2-yl)methyl)-1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxamide To a solution of 1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxylic acid (3.13 g, 15.7 mmol) in THF (100 mL) was added (3-chloropyrazin-2-yl)methanamine hydrochloride (2.8 g, 15.7 mmol), TEA (4.8 g, 47.2 mmol) and HATU (6 g, 15.7 mmol). The mixture was stirred at room temperature for 2 h. The reaction was complete detected by LCMS. The reaction mixture was treated with DCM and water, the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with DCM/THF=5/1 to give N-((3-chloropyrazin-2-yl)methyl)-1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxamide (4.7 g, 92%). 1H-NMR (CDCl3, 400 MHz) delta 1.40-1.49 (m, 1H), 1.71-1.92 (m, 3H), 2.04-2.26 (m, 2H), 2.43-2.57 (m, 1H), 2.81-2.97 (m, 1H), 3.31-3.42 (m, 1H), 4.13-4.27 (m, 2H), 4.46-4.56 (m, 1H), 4.64 (d, J=4.70 Hz, 2H), 8.29 (d, J=2.35 Hz, 1H), 8.44 (d, J=2.35 Hz, 1H).

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; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem