Tag: M.W=100-200

Electric Literature of 4774-14-5, 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. 4774-14-5, name is 2,6-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Example B-10: Preparation of (2S)-1-(4-(1-isopropyl-3-(5-methyl-5H-pyrrolo[3,2-b]pyrazin-2-yl)-1H- pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-10) cr Et3NB-10-1 B-10-2 B-10-3Preparation of 6-chloropyrazin-2-amine (B-10-2). B-10-1 B-10-2A mixture of 2,6-dichloropyrazine (300 g, 2 mol) and 28% aq. NH3 (8 L) was stirred at 14O0C in a sealed system for 14 hours. TLC (petroleum ether/EtOAc 3:1 ) indicated complete consumption of starting material. The reaction mixture was extracted with EtOAc (3 L x 3). The combined organic layers were washed with saturated aqueous NaCI (3 L), dried over Na2SO4 and concentrated in vacuo to give crude compound B-10-2, which was purified by column chromatography (silica gel, petroleum ether/EtOAc 2:1) to yield pure compound B-10-2 (410 g, yield: 59.7%) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichloropyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 23611-75-8,Some common heterocyclic compound, 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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 stirring solution of methyl 6-chloropyrazine-2-carboxylate (2.50 g, 14.49 mmol) in THF (50 mL) was added methylmagnesium bromide 3M in diethyl ether (12.07 mL, 36.2 mmol) at 0 C. The resulting mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with saturated NH4Cl (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (Redisep-24 g, 0.40 % EtOAc/n-hexane) to obtain Intermediate 105A (0.70 g, 28.00%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.44 (s, 6 H), 5.58 (br,s 1 H), 8.66 (s, 1 H), 8.86 (s, 1 H). LCMS: The compound did not ionize well.

The synthetic route of 23611-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

[0336] To 5-bromo-pyrazin-2-ylamine (0.46 g, 2.6 mmol), NaCN (1.3 g, 26 mmol) and CuCN (2.74g, 26 mmol) in a nitrogen-purged vial was added DMF (10 mL). The resulting mixture was heated at 12O0C over the weekend. After cooling down to room temperature, DMF was removed under high vacuum. The residue was partitioned between EtOAc and water. The organic extracts were combined, dried and concentrated to give the crude product as a yellow solid (0.296 g, 93%), which was used in the subsequent reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromopyrazine, its application will become more common.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); 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. 4774-14-5, name is 2,6-Dichloropyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2,6-Dichloropyrazine

To a mixture of 2,6-dichloropyrazine (12.5 g, 83.91 mmol), 4-methylbenzenesulfonic acid hydrate (32 g, 168.2 mmol), NaI (120 g, 800.6 mmol) and 1,4,7,10,13- pentaoxacyclopentadecane (10 mL, 50.35 mmol) was added thiolane 1 ,1 -dioxide (200 mL) and the mixture heated to 150 0C and stirred for 3 hrs. The mixture was allowed to cool and added water 150 ml and neutralized with solid NaHCtheta3 It was then extracted into ether (3x300ml), washed with Sat. NaHCO3, brine then dried (MgSO4) and concentrated to give an orange solid. The product was washed with water and dried under high vacuum to give 2,6-diiodopyrazine as an orange solid (8.6 g, 31%). ES+ 332. IHNMR (CDCl3) 8.73 (2H, s).

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; VERTEX PHARMACEUTICALS INCORPORATED; JIMENEZ, Juan-Miguel; STUDLEY, John; WO2010/11772; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-28-4, A common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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.

To a mixture of compound 9 (312.0 g, 2.4 mol) and K2CO3 (664.0 g, 4.8 mol) in MeOH (1.0 L) was dropwise added IC1 (704.0 g, 4.3 mol in 1.0 L of DCM) over 2 hours at 0C. Then the reaction mixture was stirred at room temperature overnight. The reaction was quenched with NaiSC aqueous solution (2M, 1.5 L). The mixture was extracted with DCM (1.0 L x 3). The combined organic phases were dried over anhydrous Na2S04, filtered and concentrated. The crude product was purified by column chromatography on silica gel (PE/EA = 10/1 to 4/1) to afford compound 10 (460 g, 75% yield) as a solid. 1HNMR (400 MHz, DMSO- 6): delta 7.68 (s, 1H), 7.07 (s, 2H). MS Calcd.: 255 MS Found: 256 ([M+H]+).

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IMARA, INC.; H. LUNDBECK A/S; SVENSTRUP, Niels; PARACHIKOVA, Anna I.; MCARTHUR, James; (133 pag.)WO2018/9424; (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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., COA of Formula: C5H7Cl2N3

To a solution of (3-chloropyrazin-2-yl)methanamine hydrochloride 22 1 a (3.1 g, 21.7 mmol), 23 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (7.1 g, 22 mmol) and 24 N,N-diisopropylethylamine (9.3 g, 72 mmol) in 25 dichloromethane (100 mL) at room temperature, 26 (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid (4.5 g, 18 mmol) was added in several batches. The resulting mixture was stirred at room temperature for 16 h. The reaction was quenched with 27 water (30 mL) and the organic phase was separated. The aqueous phase was extracted with dichloromethane (50 mL¡Á2), the combined organic phase was washed with saturated brine (50 mL¡Á2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was purified by flash column chromatography (dichloromethane/methanol 20:1) to provide 28 benzyl-(S)-3-(((3-chloropyrazin-2-yl)methyl)carbamoyl) pyrrolidine-1-carboxylate 1b(4.85 g, 13.0 mmol, yellow oil). Yield: 72%1H NMR (400 MHz, CDCl3) delta8.43 (d, J=2.4 Hz, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.37-7.26 (m, 5H), 6.92-6.85 (bs, 1H), 5.14 (s, 2H), 4.71 (d, J=4.4 Hz, 2H), 3.88-3.51 (m, 3H), 3.22-3.05 (m, 2H), 2.31-2.07 (m, 2H).

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; GUANGZHOU INNOCARE PHARMA TECH CO., LTD.; KONG, Norman Xianglong; ZHOU, Chao; CHEN, Xiangyang; US2019/177333; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6705-33-5, These common heterocyclic compound, 6705-33-5, name is Pyrazin-2-ylmethanol, 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.

To a mixture of (4-Hydroxy-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1- yl) -methanone (0.57 g, 2.0 mmol), pyrazin-2-yl-methanol [CAS 6705-33-5] (0.25 g, 2.3 mmol), and triphenylphosphine (0.57 g, 2.2 mmol) in THF (20 mL) is added DEAD (0.36 mL, 2.3 mmol). The mixture is stirred at room temperature overnight and partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2x), and the combined organic phase is dried (Na2S04) and concentrated. -The crude material is purified by SCX chromatography followed by silica gel chromatography eluting with 20% (10% 2M MeOH/CH2Cl2) /80% CH2Cl2 to 70% (10% 2M MeOH/CH2Cl2)/30% CH2C12 to yield 12 mg of the title compound. MS (ES+) 367.3

Statistics shows that Pyrazin-2-ylmethanol is playing an increasingly important role. we look forward to future research findings about 6705-33-5.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/121080; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 77112-52-8, name is Ethyl imidazo[1,2-a]pyrazine-2-carboxylate, 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 77112-52-8, Recommanded Product: Ethyl imidazo[1,2-a]pyrazine-2-carboxylate

Step 2: 5, 6,7, 8-Tetrahydroimidazo [1, 2-a] pyrazine-2-carboxylic acid ethyl ester, Hydrochloride : 0.46 M HCI EtOH (169 mL) and 10% Pd-C (50% wet) (1.37 g) were added to the EtOH (546 mL) solution of imidazo [1,2-a] pyrazine-2-carboxylic acid ethyl ester (13.7 g). The mixture was hydrogenated under H2 at 40 psi at room temperature for 15 h. The reaction mixture was filtered and Pd-C was washed with EtOH. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with CHCis-MeOH (9/1-2/1). The titled compound was obtained as brown crystals Yield : 10.4 g, 63%. ‘H NMR (CDCI3) d 1.38 (t, 3H, J = 7.1 Hz), 3.90 (t, 2H, J = 5.7 Hz), 4.40 (q, 2H, J = 7.1 Hz), 4.59 (t, 2H, J = 5.7 Hz), 4.80 (s, 2H), 8.20 (s, 1 H).

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; WYETH; WO2003/93277; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 356783-15-8, 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. 356783-15-8, name is 3,6-Dichloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

(b) In 2.0 mL of methylene chloride was suspended 0.2 g of 3,6-dichloro-2-pyrazinecarboxylic acid. Then, 0.001 mL of N,N-dimethylformamide and 0.14 mL of oxalyl chloride were successively added at an ice-cooled temperature, and the mixture thus formed was stirred at room temperature for 40 minutes. The reaction mixture was concentrated to dryness under reduced pressure and then dissolved in 3.0 mL of acetonitrile. Then, 0.3 g of potassium fluoride and 0.056 g of 18-crown-6-ether were added and the mixture thus formed was stirred at 60 C. for 2.5 hours in an atmosphere of nitrogen gas. The reaction mixture was poured into 3.0 mL of methanol, the insoluble matter was filtered off, and then the filtrate was concentrated to dryness under reduced pressure. The residue was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate-9:1] to obtain 0.15 g of methyl 3,6-difluoro-2-pyrazinecarboxylate as a colorless oily product.

The chemical industry reduces the impact on the environment during synthesis 3,6-Dichloropyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 19745-07-4, The chemical industry reduces the impact on the environment during synthesis 19745-07-4, name is 2,5-Dichloropyrazine, I believe this compound will play a more active role in future production and life.

To a stirred solution of cesium carbonate (492 g, 1510 mmol) in DMF (1000 mL) was added (S)-(2, 2-dimethyl-l, 3-dioxolan-4-yl) methanol (133 g, 1007 mmol) at 0 C. The resulting reaction mixture was stirred at room temperature for 30 min. Then a solution of 2, 5-dichloropyrazine (150 g, 1007 mmol) in DMF (500 mL) was added at 0 C and the resulted reaction mixture was stirred at 100 C for 4 h. (TLC System: 20% Ethyl acetate in Petether, R 0.5, UV active). The reaction mixture was diluted with ice cold water (500 mL), extracted with EtOAc (3 x 300 mL). The combined organic layer was washed with water (2 x 200 mL) and brine solution (100 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to obtain crude compound. The crude compound was purified by flash column chromatography (silica gel: 100-200 mesh, eluent: 10 % EtOAc in Hexane) to afford the desired product (,S)-2-chloro-5-((2, 2-dimethyl-l, 3- dioxolan-4-yl) methoxy) pyrazine (200 g, 768 mmol, 76 % yield) as a yellow liquid. LCMS (m/z): 245.1 [M+H]+.

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, 2,5-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem