Tag: M.W=200-300

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

116] Step 1. 2-(1.1.2.2.3.3.4.4-dR-4-((5.6-Diphenylpyrazin-2-viyperdeutero-propan-2- yl)amino)butan-l-ol (12a). To a solution of commercially available 5-chloro-2,3- diphenylpyrazine (10) (0.56 g, 2.10 mmol) in NMP (2.1 mL) was added dis-aminoalcohol 11a (0.46 g, 3.15 mmol, 1.5 equiv, prepared as described in Example 8). The reaction vessel was sealed and heated to 190 0C for 15 hours, then cooled to ambient temperature. The mixture was diluted with ice water and extracted with Et2O (3 x 20 mL). The combined organic layers were washed successively with water and brine. The resulting organic layer was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 30-50% EtO Ac/heptane) to afford 12a (0.13 g, 16%). MS (M+H): 377.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41270-66-0, its application will become more common.

Reference:
Patent; CONCERT PHARMACEUTICALS, INC.; HARBESON, Scott L.; MASSE, Craig E.; LIU, Julie F.; WO2011/17612; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 344940-70-1, 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. 344940-70-1 name is 5-Bromo-3-phenylpyrazin-2-amine, 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.

Into a flask, purged with an inert atmosphere of nitrogen, was placed 5-bromo-3-phenylpyrazin-2-amine (300 mg, 1.20 mmol) in EtOH (5.22 mL). 2-Bromo-l,l-diethoxyethane (372 mu, 2.40 mmol) and HBr in water (950 mu, 8.40 mmol) were added. The mixture was warmed at 85C. After 2.5 h, the reaction was cooled to ambient temperature and diluted with EtOAc. The mixture was further cooled to 0C and slowly quenched with saturated aqueous NaHC03 until the pH was adjusted to 9. The resulting solution was extracted with EtOAc (3X). The organic layers were combined and dried over anhydrous sodium sulfate. The solid was filtered and the filtrate was concentrated in vacuo to dryness. The residue was purified by silica gel chromatography with EtOAc:hexanes (0-70%) to afford the title compound.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; CAMPBELL, Brian, T.; DONG, Guizhen; GARFUNKLE, Joie; KIM, Alexander; ORNOSKI, Olga; PARKER, Dann, L., Jr.; RAGHAVAN, Subharekha; XU, Libo; YANG, Zhiqiang; (191 pag.)WO2015/187470; (2015); 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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., category: Pyrazines

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

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:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, A new synthetic method of this compound is introduced below., Formula: C4H3Br2N3

(a)To a 100 mL autoclave was added 2-amino-3,5-dibromopyrazine (10 g, 39.54 mmol, 1 eq) and aqueous ammonia (50 mL, commercially available).The temperature was raised to 130 C under nitrogen atmosphere to carry out the reaction overnight (10 to 12 hours); the temperature was lowered, suction filtration, and the obtained solid was vacuum dried to obtain 5.0 g of compound II.

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Derivative Biological Technology Co., Ltd.; Liu Ke; (7 pag.)CN108707150; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, 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 63744-22-9, Product Details of 63744-22-9

To a solution of 4-(4- (oxetan-3-yl)piperazin- l-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)aniline XXIV (619 mg, 2.17 mmol) and 6,8-dibromoimidazo[l,2-a]pyrazine (601 mg, 2.2 mmol) in IPA (15 mL) was added N,N-Diisopropylethylamine (0.95 ml, 5.43 mmol). The mixture was stirred at 110 C for 16 h. After this time, DCM (10 mL) and sat aqueous NaHC03 (15 mL) were added. The aqueous layer was separated and extracted with DCM (2 x 10 mL). The combined organic extracts were washed with brine (10 mL) and dried over sodium sulfate. The resulting residue was purified by column chromatography ISCO Rf (24 g column) eluting with a gradient of 100% DCM – 60:35:5 DCM : Et20 : MeOH to provide 6-bromo-N- (4-(4-(oxetan-3-yl)piperazin-l-yl)-3-(2-((tetrahydro-2H-pyran-2- yl) oxy)ethoxy)phenyl)imidazo [ 1 ,2- a] pyrazin- 8 -amine XXV .

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, 6,8-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KROPF, Jeffrey E.; LEE, Seung H.; LO, Jennifer R.; MITCHELL, Scott A.; SCHMITT, Aaron C.; XIONG, Jin-Ming; XU, Jiangjun; ZHAO, Zhongdong; WO2015/100217; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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 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 dichloromethane (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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6,8-Dibromoimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; Incyte Corporation; Douty, Brent; Burns, David M.; Combs, Andrew P.; Jia, Zhongjiang; Levy, Daniel; Yue, Eddy W.; US2020/71335; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 957344-74-0, These common heterocyclic compound, 957344-74-0, name is 5,8-Dibromoimidazo[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.

Step 3 (5-Bromo-imidazo[l,2-a]pyrazin-8-yl)-[4-(4-isopropyl-piperazin-l-yl)-phenyl] -amine[00395] A solution of 5,8-dibromo-imidazo[l,2-a]pyrazme (0 134g, 0 48mmol), 4-(4-isopropyl- piperazm-l-yl)-phenylamine (0 118g, 0 54mmol) and dnsopropylethylamme (0 093mL, 0 54mmol) is stirred at 9O0C for 18 hours The reaction mixture is concentrated in vacuo and partitioned between DCM and sat NaHCO3 The organic layer is washed with brine, d?ed over MgSO4, filtered and concentrated The residue is pu?fied by silica gel column chromatography eluting with 98 2 DCM MeOH to afford the title compound (0 086 g, 43%)

The synthetic route of 957344-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 193966-70-0, 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. 193966-70-0, name is Methyl 5-(bromomethyl)pyrazine-2-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Part B. Methyl 5-[(1-Pyrrolidinyl)methyl]pyrazine-2-carboxylate. STR471 By essentially following the procedure used to prepare Example 137, Part B, the title compound was prepared from methyl 5-(bromomethyl)pyrazine-2-carboxylate (Part A) and pyrrolidine in 85% yield as a pale yellow oil. The mixture was subjected to flash chromatography on silica gel, eluding with a gradient of EtOAc(100-95%)/Et3 N(0-5%). 1 H NMR (CDCl3) delta 9.23 (s, 1H), 8.78 (s, 1H), 4.03 (s, 3H), 3.90 (s, 2H), 2.59 (br s, 4H), 1.82 (br s, 4H).

The synthetic route of Methyl 5-(bromomethyl)pyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6025382; (2000); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1379338-74-5, 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. 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(E) ie/t-buty. 3-((7-chioropyrido[4.3-??]pyrazi n-5-ylami no)methyl)-4- hydroxypiperidi ne-1 -carboxylate.5,7-dichloropyrido[4,3-?>]pyrazine (3.6 g, 18 mmol) and DIPEA (2.8 g, 21 .6 mmol) was added to a solution of ferf-buty. terf-buty. 3-(aminomethyi)-4-{terf~butyldimethyisiiyioxy)piperidine-1 -carboxylate (6.2 g, 18 mmol) in THF (20 mL) and the mixture was refluxed overnight. The volatile components were evaporated and the residue was extracted with ethyl acetate. Ethyl acetate was washed with brine and dried. The solvent was removed and the residue was re-dissolved in THF (16 mL) and TBAF was added in. The reaction mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate, washed with brine, then dried, filtered, and concentrated in vacuo. The crude residue was purified by flashchromatography to give the title compound (3.35 g, 47% yield). MS (m/z): 394(M+H)+.

The synthetic route of 5,7-Dichloropyrido[3,4-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; JI, Jianguo; WO2012/167423; (2012); 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