Tag: M.W=100-200

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. 4774-14-5, name is 2,6-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H2Cl2N2

To a solution of fert-butyl azetidin-3-ylcarbamate hydrochloride (LXIII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXIV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous NaaSO/t, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1 : 1) to yield fert-butyl (l -(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17CIN4O2 mlz 285.1 (M+H).

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 4774-14-5.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (247 pag.)WO2017/24004; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-80-1, 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 36070-80-1 as follows.

General procedure: The corresponding substituted salicylanilide 2 (1 mmol) and 5-chloropyrazine-2-carboxylic acid 1 (1 mmol) were dissolved in dryDMF (8 mL), the solution was cooled to 10 C and DCC (1.2 mmol)was added in three portions during 1 h. The mixture was stirred foradditional 3 h at the same temperature and then stored at 4 C for20 h. The precipitate of N,N0-dicyclohexylurea was removed byfiltration and the solvent was evaporated in vacuo till dryness. Thecrude products 3 were purified by one or repeated crystallizationfrom ethyl acetateehexane mixture.

According to the analysis of related databases, 36070-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Baranyai, Zsuzsa; Kratky, Martin; Vin?ova, Jarmila; Szabo, Nora; Senoner, Zsuzsanna; Horvati, Kata; Stola?ikova, Ji?ina; David, Sandor; Bosze, Szilvia; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 692 – 704;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 15707-23-0, name is 2-Ethyl-3-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 15707-23-0, Computed Properties of C7H10N2

A mixture of 2-methyl-3-ethylpyrazine (22.35g, 183mmol), selenium dioxide (30g, 270mmol), and diatomaceous earth (30g) in dioxane (250ml) was heated at reflux for 18 hours. The mixture was allowed to cool and the solid material removed by filtration through diatomaceous earth. The filter pad was washed with methanol several times and the volatiles removed from the combined filtrate by evaporation. The residue was purified by chromatography on silica gel eluting eluting with EtOAC/hexanes (0:100 increasing in polarity tol5:85) to give 3-ethylpyrazine-2-carboxaldehyde (3.Og, 12%); NMR Spectrum 1.22 (t, 3H), 3.19 (q, 2H), 8.78 (s, IH), 8.80 (s, IH), 10.10 (s, IH).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106307; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 27398-39-6, name is 3-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 27398-39-6, Safety of 3-Chloropyrazine-2-carboxylic acid

To a solution of 3-chloropyrazine-2-carboxylic acid (100 mg, 0.63 mmol) in DCM/MeOH (2 mL: 0.2 mL) was added TMSCHN2 (0.47 mL, 0.95 mmol) at RT and the resulting mixture stirred at RT for 2 h. Acetic acid (0.2 mL) was added and the mixture diluted with water (2 mL) and extracted with DCM (4 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to give the title compound as an oil. LRMS m/z (M+H) 173.0 found, 173.0 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Douglas; LUO, Yunfu; MENG, Na; YU, Tingting; (114 pag.)WO2016/65585; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4858-85-9, name is 2,3-Dichloropyrazine, 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 4858-85-9, category: Pyrazines

A mixture of 2,3-dichloropyrazine (5.0 g, 34 mmol), N-methylpiperazine (5.1 g, 51 mmol) and potassium carbonate (7.0 g, 51 mmol) in acetonitrile (100 mL) was stirred at ambient temperature for 2 h. Addition of hexane, followed by filtration and concentration of the filtrate gave 7.3 g of the crude product as an orange liquid. Purification by filtration through silica using heptane/EtOAc (3: 1) followed by EtOAc/acetone (1: 1) gave 4.1 g (57%) of the title compound as a yellow oil which solidified upon cooling. HPLC purity: 100%. MS m/z 213 (M+H) +. *Reported in WO 00/76984, Example 169, Step 1.

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; BIOVITRUM AB; WO2004/9586; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-75-4, These common heterocyclic compound, 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, 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.

A solution of tert-butyl 4-((2S,3R,4R)- I -acetyl-4-amino-2,3-dimethyl- I ,2,3,4-tetrahydroq uinolin-6- yl)piperazine-1-carboxylate (for a preparation see Intermediate 213, 69 mg, 0.151 mmol) in NMP (1.5 mL) was treated with 5-chloropyrazine-2-carbonitrile (22 mg, 0.158 mmol) and DIPEA (0.079mL, 0.453 mmol) then the mixture was heated at 200 C for 30 mm using a microwave reactor. The residue was purified by MDAP (Formic). The desired fractions were combined and evaporated in vacuo to afford the desired product as a white solid (17 mg).LCMS (2 mm Formic): Rt = 0.82 mi [MH] = 407.

The synthetic route of 36070-75-4 has been constantly updated, and we look forward to future research findings.

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

Application of 160252-31-3, 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. 160252-31-3 name is 1-(5-Chloropyrazin-2-yl)ethanone, 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.

A mixture of (4-(3-(cyclopropylmethoxy)phenoxy)-2,6-difluorophenyl)methanol (60 mg), 1-(5-chloropyrazin-2-yl)ethanone (33.7 mg), sodium hydride (60% in oil, 11.75 mg) and THF (1 ml) was stirred at room temperature for 10 min, and then stirred under microwave irradiation at 135C for 1 hr. To the mixture was added water at 0C, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by HPLC (acetonitrile/water, addition of 0.1% TFA) to give the title compound (20 mg). 1H NMR (300 MHz, CDCl3) delta 0.31-0.42 (2H, m), 0.61-0.70 (2H, m), 1.22-1.30 (1H, m), 2.66 (3H, s), 3.79 (2H, d, J = 7.0 Hz), 5.47 (2H, s), 6.53-6.68 (4H, m), 6.76 (1H, ddd, J = 8.3, 2.4, 0.8 Hz), 7.27-7.34 (1H, m), 8.18-8.23 (1H, m), 8.81-8.88 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(5-Chloropyrazin-2-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIZOJIRI, Ryo; ASANO, Moriteru; TOMITA, Daisuke; BANNO, Hiroshi; TAWADA, Michiko; NII, Noriyuki; GIPSON, Krista E.; MAEZAKI, Hironobu; TSUCHIYA, Shuntaro; IMAI, Mayumi; AMANO, Yuichiro; (100 pag.)EP3279183; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 98-97-5, 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. 98-97-5, name is Pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Figure ID shows a table of products produced by using a catalytic redox system comprising 20 mol % organocatalyst lg and 10 mol % CuI2(NMI)4 in MeCN under dry air (4 A molecular sieves) at 50 C, a variety of amides were constructed from 1.0 equiv of a carboxylic acid, 1.2 equiv of an amine, and 1.5 equiv of triethyl phosphite. For workup and isolation, the MeCN was filtered, and the solids were washed with CH2C12. The solvents were evaporated, and the products were obtained by Si02 chromatography. The entries span 1 and 2 amines, aliphatic and aromatic amines, amino acids and amino alcohols/phenols. The method is compatible with oxidation-prone substrates such as alkenes, boron derivatives, and furans and indoles as well as with electron-deficient heterocycles and benzene derivatives, and it works well for amines with a significant range of piH), chiral amine partners, chiral acid partners, and others. No racemization of stereocenters was observed for those substrates studied. The synthesis of peptide 3a shown in was carried out on a 5 g scale and delivered the product in 91% yield after 24 h at 50 C.

The chemical industry reduces the impact on the environment during synthesis Pyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EMORY UNIVERSITY; LIEBESKIND, Lanny Steven; GANGIREDDY, Pavan Kumar Reddy; AKONDI, Sri Rama Murthy; (97 pag.)WO2017/70157; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 681249-57-0, 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. 681249-57-0 name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, 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.

5.119 3-(1-OXO-4-((3-((2-(TRIFLUOROMETHYL)-5,6-DIHYDRO-[1,2,4]TRIAZOLO[1,5-A]PYRAZIN-7(8H)-YL)METHYL) BENZYL)OXY)ISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE To the stirred solution of 3-(4-(3-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (500 mg, 1.13 mmol) in DCM (10 mL) was added 2-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (238 mg, 1.24 mmol) and DIPEA (0.59 mL, 3.38 mmol). The resulting solution was stirred at 40 C. for 27 hrs. The reaction mixture was added by DCM (30 mL) and brine (20 mL). The mixture was extracted and organic layer was dried by MgSO4 and concentrated. The residue was purified by give a glass like solid. The solid was stirred in EtOAc (5 mL) and stirred in diethyl ether (40 mL) to give 3-(1-oxo-4-((3-((2-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)methyl)benzyl)oxy)isoindolin-2-yl)piperidine-2,6-dione as a white solid (391 mg, 62% yield); HPLC: Waters Symmetry C-18, 3.9*150 mm, 5 mum, 1 mL/min, 240 nm, 50/50, (CH3CN/0.1% H3PO4), 3.25 min (95.7%); mp: 213-215 C.; 1H NMR (DMSO-d6) delta 1.92-2.06 (m, 1H, CHH), 2.34-2.47 (m, 1H, CHH), 2.53-2.64 (m, 1H, CHH), 2.82-3.07 (m, 3H, CHH, CH2), 3.81 (s, 4H, CH2, CH2), 4.17-4.49 (m, 4H, CHH, CHH, CH2), 5.05-5.16 (m, 1H, CHH), 5.27 (s, 2H, CH2), 7.28-7.54 (m, 7H, Ar), 10.97 (s, 1H, NH); 13C NMR (DMSO-d6) delta 22.33, 31.16, 45.09, 46.52, 47.73, 49.14, 51.58, 59.55, 69.55, 115.13, 115.28, 126.72, 128.06, 128.44, 128.59, 129.77, 129.96, 133.30, 136.81, 137.47, 152.82, 153.45, 167.96, 170.95, 172.78; LCMS MH=555; Anal. Calcd for C27H25F3N6O4: C, 58.48; H, 4.54; N, 15.16; Found: C, 58.53; H, 4.21; N, 14.89.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-28-4, 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 33332-28-4 as follows.

6-Pyridin-3-ylpyrazin-2-amine An oven dried resealable Schlenk tube was charged with 6-chloropyrazin-2-amine (0.73 g, 5.71 mmol), 3-pyridineboronic acid (0.91 g, 7.42 mmol), dioxane (50 mL) and a 2M aqueous solution of cesium carbonate (8.5 mL, 17.13 mmol). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1 ,1′- bis(diphenylphosphino)ferrocene-palladium(ll) dichloride dichloromethane complex (290mg, 0.35 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 9O0C oil bath. After 16h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel flash chromatography (95:5 dichloromethane/methanol) to give the title compound (845 mg, 86percent) as a solid. delta 1H-NMR (CDCI3): 9.18 (s, 1H), 8.67 (d, 1H), 8.38 (s, 1H), 8.25 (m, 1H), 7.99 (s, 1 H), 7.41 (m, 1 H), 4.77 (s, 2H). ESI/MS (m/e, percent): 172 [(M+1)\ C9H8N4].

According to the analysis of related databases, 33332-28-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL PRODESFARMA, S.A.; WO2007/17096; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem