Tag: M.W=100-200

Adding some certain compound to certain chemical reactions, such as: 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine, 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 38557-72-1. 38557-72-1

General procedure: l-Boc-3-hydroxypiperidine (CAS 85175-45-2, 0.41 g, 2.05 mmol) was stirred in DMF (1.65 mL), at rt, and then a 60% NaH dispersion in mineral oil (0.082 g, 2.05 mmol) was added. Then 4-chloro-2,6-dimethylpyridine (CAS 3512-75-2, 0.26 mL, 2.05 mmol) in DMF (0.64 mL) was added dropwise at rt. The mixture was stirred overnight at 60 C. The mixture was evaporated diluted with FLO and was extracted with EtOAc. The organic layer was separated, dried (Na2S04), filtered and evaporated, in vacuo. The residue was purified by flash column chromatography (silica; EtOAc in heptane 0/100 to 30/70). The desired fractions were collected and concentrated in vacuo to yield intermediate 22 (0.32 g, 51%) as a colorless oil(0656) Intermediate 129 was prepared following an analogous procedure to the one described for the synthesis of intermediate 22 using 2-chloro-3,5-dimethylpyrazine (CAS 38557- 72-1) as starting material and THF as solvent.

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 2-Chloro-3,5-dimethylpyrazine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; DE LUCAS OLIVARES, Ana Isabel; VEGA RAMIRO, Juan, Antonio; (224 pag.)WO2019/243531; (2019); 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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., 4858-85-9

A. Preparation of the intermediate compounds; Example Al; a) Preparation of intermediate compound 1; Reaction in microwave oven. A mixture of 2-phenoxyethanamine (0.010 mol), 2,3- dichloropyrazine (0.012 mol) and l,8-diazabicyclo(5.4.0.)undec-7-ene (DBU) (0.012 mol) in CH3CN (20 ml) was heated for 20 minutes at 180 0C. The solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2). The product fractions were collected and the solvent was evaporated. Yield: 2.5 g of intermediate compound 1 (quantitative yield; used in next reaction step, without further purification).

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; JANSSEN PHARMACEUTICA N.V.; WO2007/71646; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19838-08-5, Name is 3-Methylpyrazin-2-amine, 19838-08-5, 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.

(iii) A solution of bromine (0.26 ml) in chloroform (40 ml) was added dropwise to a stirred solution of 2-amino-3-methylpyrazine (0.453 g) and pyridine (0.4 ml) in chloroform (100 ml) with shielding from sunlight, over a period of 1 hour. The reaction mixture was stirred for a further 30 minutes and then water (25 ml) was added. The organic layer was separated, dried (MgSO4) and evaporated to afford a brown oil. The oil was purified by chromatography on silica gel, eluding with dichloromethane, to give 2-amino-5-bromo-3-methylpyrazine as a white solid (0.312 g, 28%), m.p. 51-52 C.; mass spectrum (+ve CI): 188 (M+H)+.

Statistics shows that 3-Methylpyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 19838-08-5.

Reference:
Patent; Zeneca Limited; US5861401; (1999); A;,
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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., 55557-52-3

To a solution of 3-chloropyrazine-2-carbonitrile (15.0 g, 108 mmol) in AcOH (200 mL) was added Raney Ni (3 g, in water), and the mixture was stirred for 48 h under an atmosphere of hydrogen with a balloon at rt. The mixture was filtered and the filtrate was concentrated in vacuo to give a crude product, which was dissolved in 250 mL of aqueous HC1 (2M) and extracted with EtOAc (200 mL x 2). The aqueous layer was concentrated under vacuo to give 14.5 g of (3-chloropyrazin-2-yl)methanamine hydrochloride as a brown solid which was used in the next step without further purification.

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; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David; OWENS, Timothy D.; (121 pag.)WO2016/210165; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-29-5, 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. 33332-29-5, name is 2-Amino-5-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 22 5-Methoxypyrazin-2-amine [0242] To a solution of 5-chloropyrazin-2-amine (0.2 g, 1.54 mmol) in MeOH (3 mL) was added Cu powder (0.13 g, 2.07 mmol), followed by a solution of sodium methoxide in MeOH (0.38 mL, 1.75 mmol). The reaction mixture was stirred at 150 C. in a sealed tube for 24 h. The reaction mixture was then filtered through Celite, and the filtrate was concentrated in vacuo. The crude product obtained was purified by column chromatography (silica: 100-200 mesh, MeOH: DCM 2-3%) to afford the title compound (0.13 g, 67%). LCMS (ES+) 126 (M+H)+, RT 1.06 minutes (method 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; Brookings, Daniel Christopher; Ford, Daniel James; Franklin, Richard Jeremy; Ghawalkar, Anant Ramrao; Kulisa, Claire Louise; Neuss, Judi Charlotte; Reuberson, James Thomas; US2014/315885; (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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., 486460-21-3

Comparative Example 1: Preparation of Compound of formula 2 wherein R is Boc, according to the method disclosed in U.S. Patent No. 6,699,871, Example 7, STEP A [42] (R)-3-Boc-amino-4-(2,4,5-trifluorophenyl)-butanoic acid (50.1mg, 0.15mmol) was dissolved in dichloromethane (2.5ml) and 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-alpha]pyrazine (39.2mg, 0.20mmol) was added thereto. While maintaining a temperature of 0 to 5C, HOBT (17.2mg, 0.21mmol) was added to the mixture, followed by reaction for 10 minutes. Thereafter, EDC (48.3mg, 0.25mmol) was added at 0C, and the reaction mixture was warmed to room temperature and stirred for 14 hours. After the reaction was completed, the reaction liquid was concentrated under reduced pressure and a desired compound was purified by column chromatography eluting with 100% ethyl acetate to afford 29mg (yield: 47.5%) of the title compound as a solid.

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; ST PHARM CO., LTD.; LIM, Geun Gho; CHANG, Sun Ki; BYEON, Chang Ho; WO2012/99381; (2012); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

27398-39-6, A common heterocyclic compound, 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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 solution of ethyl 5-(piperazin-1-yl) benzofuran-2-carboxylate (1 mmol) in dry dichloromethane (3 mL) was added triethylamine (2 mmol) and corresponding acid (1 mmol) at 0¡ãC. Propylphosphonic anhydride solution (50 wtpercent in ethyl acetate; 2.5 mmol) was then added drop wise to the reaction mixture and was stirred at rt for 6 h (monitored by TLC & LCMS for completion). The reaction mixture was then washed with water (2 mL), brine (2 mL), and dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was then recyrstallised from diethyl ether.

The synthetic route of 27398-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Renuka, Janupally; Reddy, Kummetha Indrasena; Srihari, Konduri; Jeankumar, Variam Ullas; Shravan, Morla; Sridevi, Jonnalagadda Padma; Yogeeswari, Perumal; Babu, Kondra Sudhakar; Sriram, Dharmarajan; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4924 – 4934;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 33332-25-1

To a solution of methyl 5-chloropyrazine-2-carboxylate (601 mg, 3.48 mmol) in THF (11.6 mL) was added 1-cyclohexene-l-yl-boronic acid (656 mg, 5.21 mmol), K3PO4 (1.47 g, 6.91 mmol), Pd(OAc)2 (39.2 mg, 0.175 mmol), SPhos (144 mg, 0.350 mmol) and H2O (0.13 mL, 7.2 mmol) at room temperature. After stirring for 15 h at 40 C, the reaction was quenched by adding water. The crude products were extracted with EtOAc (3X), and the combined organic extracts were washed with brine, dried (MgS04), and concentrated in vacuo. The residue was purified by flash column chromatography (hexane/EtOAc = 9/1 to 4/1) to afford methyl 5-(cyclohex-l-en-l-yl)pyrazine-2-carboxylate (736 mg, 97%) as a pale yellow solid. NMR (300 MHz, CDCh) delta 9.21 (d, J= 1.2 Hz, 1H), 8.81 (d, J= 1.2 Hz, 1H), 6.98-7.01 (m, 1H), 4.05 (s, 3H), 2.55-2.60 (m, 2H), 2.34-2.38 (m, 2H), 1.81-1.89 (m, 2H), 1.70-1.77 (m, 2H).

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, 33332-25-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

55557-52-3, 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below.

Preparation 228N-(3-Cyanopyrazin-2-yl)-N-methylbenzenesulfonamide10721] To a solution of 2-chloro-3-cyanopyrazine (5 g,35.94 mmol) and Cs2CO3 (16.27 g, 50 mmol) in acetonitrile(75 mE) was added N-methylbenzenesulfonamide (7.37 g, 43mmol) and the reaction heated to 80 C. for 3 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between water and EtOAc. The organic layer was collected, dried, concentrated in vacuo and purified by silica gel column chromatography eluting with 50% EtOAc in hexanes to afford the title compound (7.2 g, 73%). ?H NMR (400 MHz, DMSO-d5): oe ppm 3.12 (s, 3H), 7.64 (m, 4H), 7.76 (m, 1H), 8.80 (d, 1H), 8.85 (d, 1H).

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; Pfizer Inc.; Coe, Jotham Wadsworth; Dehnhardt, Christoph Martin; Jones, Peter; Sabnis, Yogesh Anil; Strohbach, Joseph Walter; Wakenhut, Florian Michel; Whitlock, Gavin Alistair; (180 pag.)US2015/329542; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, 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. 4858-85-9

To a 1.0 M solution of LiHMDS in toluene (14.8 mL, 14.8 mmol) under nitrogen at 0 C was added 2,3-dichloropyrazine (0.699 mL, 6.71 mmol) and ethyl acetate (0.725 mL, 7.38 mmol). The mixture was stirred overnight for 18 hours, allowing the ice bath to warm to room temperature. The mixture was poured into saturated ammonium chloride (100 mL), and extracted with diethyl ether (3×100 mL). The combined ether extracts were washed with brine, dried (sodium sulphate) and evaporated. The residue was chromatographed (40 g silica cartridge, 0-25% ethyl acetate/petroleum benzine 40-60 C) to give the title compound (199) (0.414 g, 31 % yield) as a pale yellow oil; 1 H NMR (400 MHz, CDCI3) delta 8.46 (d, J = 2.5 Hz, 1 H), 8.31 (d, J = 2.5 Hz, 1 H), 4.22 (q, J = 7.1 Hz, 2H), 4.03 (s, 2H), 1.27 (t, J = 7.1 Hz, 3H). LCMS Method C: rt 5.16 min.

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 4858-85-9.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem