Tag: M.W=200-300

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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H8ClF3N4

Into a 50 mL round-bottom flask was added 20 mL dichloromethane, followed by the addition of phenyl-butyric acid derivative (3.73 g, 0.01 mol) and triazolopyrazine hydrochloride (228 g, 0.01 mol). The temperature of the reaction mixture was cooled down to 0 C. in an ice-salt bath. 1-Hydroxylbenzotriazole (1.62 g, 0.012 mol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.29 g, 0.012 mol) were further added. 3 g Triethylamine was then added dropwise and the mixture was stirred at room temperature for 24 h. The reaction solution was washed with 3×20 mL distilled water. The obtained organic layers were collected and dried over anhydrous magnesium sulfate for 1 h. Then, the desiccant was filtered off and the resulting reactant was concentrated to 4.64 g. The yield was 85%.

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 762240-92-6.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, molecular formula is C10H15N3O2, 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. category: Pyrazines

Step 2: 5-Methyl-2-aminopyrazine. To a stirred solution of (5-methyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (2.1 g, 10 mmol) in 30 mL CH2Cl2 at 0 C. under nitrogen was added trifluoroace (30 mL). The solution was allowed to warm to RT overnight. The solution was rotary evaporated to remove TFA and the residue was redissolved in 200 mL CH2Cl2 and stirred with 100 mL 10% Na2CO3. The organics were isolated and the aqueous solution extracted 3*100 mL with CH2Cl2. The organics were combined, dried (MgSO4), filtered and concentrated to an orange solid (1 g, 92%). 1H-NMR (400 MHz, CDCl3) delta8.46 (s, 1H), 7.70 (s, 1H), 2.49 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 369638-68-6, its application will become more common.

Reference:
Patent; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 76537-18-3, 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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

A 40 mL vial was charged with 3-bromo-5-chloropyrazin-2-amine (150 mg, 0.72 mmol, Ark Pharm), cesium fluoride (328 mg, 2.16 mmol), 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (178 mg, 0.79 mmol, Combi-blocks), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (13 mg, 0.018 mmol), l-butanol (3 mL), and water (0.75 mL). The mixture was sparged with N2 for 5 min, then heated to 60 C for 1H. The reaction mixture was partitioned between water and EtOAc, and the layers were separated. The organic layer was washed with brine, dried over MgSCL, filtered, and concentrated. The residue was purified by flash chromatography (0-100% EtO Ac/hexanes) to afford the title compound as a tan solid (140 mg, 86%). LCMS calculated for CXFLC1N4S (M+H)+: m/z = 227.0, found: 227.0.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-chloropyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; SHVARTSBART, Artem; COMBS, Andrew, P.; FALAHATPISHEH, Nikoo; POLAM, Padmaja; SHAO, Lixin; SHEPARD, Stacey; (170 pag.)WO2019/126505; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 622392-04-5,Some common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, 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.

2-bromo-5-iodopyrazine (503 mg, 1.77 mmol) and tert-butyl piperazine-1-carboxylate (355 mg, 1.91 mmol) were taken up in tBuOH (8 mL). iPr2NEt (400 muL, 2.3 mmol) was added and the stirred reaction mixture was heated to 100 C. After 66 h, the reaction mixture was cooled and was partitioned between EtOAc, water and brine. The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (10-30% EtOAc in hexanes) to afford tert-butyl 4-(5-iodopyrazin-2-yl)piperazine-1-carboxylate 7.11.

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

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3,Some common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, molecular formula is C4H3BrClN3, 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.

Into a three-neck flask equipped with a reflux pipe were put 2.48 g of 3-bromo-5-chloropyrazin-2-amine, 2.19 g of 5-chloro-2-methoxyphenylboronic acid, 2.26 g of potassium fluoride, and 43 mL of tetrahydrofuran, and the air in the flask was replaced with nitrogen. The mixture in the flask was degassed by being stirred under reduced pressure, and then 0.44 g of tris(dibenzylideneacetone)dipalladium(0) and 4.0 mL of tri-t-butyl phosphine were added thereto. The mixture was reacted by being stirred at 80 C for 42 hours. After a predetermined time elapsed, the obtained mixture was suction-filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography using a developing solvent (toluene: ethyl acetate = 10: 1), whereby 1.00 g of 2,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3- )]pyrazine, which was a target substance, was obtained in a yield of 31 %. A synthesis scheme of Step 1 is shown in (b-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-5-chloropyrazin-2-amine, its application will become more common.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; YAMAGUCHI, Tomoya; YOSHIZUMI, Hideko; KIDO, Hiromitsu; TAKAHASHI, Tatsuyoshi; SEO, Satoshi; (162 pag.)WO2018/122664; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 23229-25-6, These common heterocyclic compound, 23229-25-6, name is 2,6-Dibromopyrazine, 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.

19a) 4- (6-BROMO-PYRAZIN-2-YI)-MORPHOLINE PBr3 (11 g, 36.9 mmol, 5.5 eq) is added to 2, 6-dichloro-pyrazine (1.0 g, 6.7 mmol, 1 eq) at rt and heated to 150 °C for 24 h. This solution is dried in vacuum and the residue is dissolved in CH2CI2 (50 mL). The organics are washed with H20, brine and dried. Morpholine is added to this solution dropwise at 0 °C and warmed to rt in 5 h. The solution is washed with H20 and brine. Chromatography (SiO2, 10-60percent EtOAc-hexanes gradient elution) provides product 4-(6-BROMO-PYRAZIN-2-YL)-MORPHOLINE (0.5 g, 31 percent). MS/ESI, M+1 = 246.01, H NMR (400 MHz, CDCI3) 8 7.99 (s, 1 H), 7.95 (s, 1 H), 3.82 (t, J = 4.0 Hz, 4H), 3.58 (t, J = 4.0 Hz, 4H).

Statistics shows that 2,6-Dibromopyrazine is playing an increasingly important role. we look forward to future research findings about 23229-25-6.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/28444; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 21943-17-9, name is 5-Bromo-3-chloropyrazin-2(1H)-one, 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 21943-17-9, Recommanded Product: 21943-17-9

General procedure: A solution of 56 (1.50 g, 7.16 mmol), the appropriate secondary amine (8.59 mmol, 1.20 equiv) and diisopropylethylamine (1.50 mL, 8.59 mmol) in n-butanol (15 mL)was heated in a microwave reactor using variable wattage to 140 C for 1 h. The mixture was concentrated and purified by flash column chromatography on silica, eluting with 9:1 dichloromethane/methanol, to give gave 58-63.

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, 5-Bromo-3-chloropyrazin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728,16;; ; Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728;,
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. 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl (5-methylpyrazin-2-yl)carbamate

Example 76; (3R)-1-{2-[(5-Methylpyrazin-2-yl)amino]-2-oxoethyl}-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide (Isomer 1); a) 2-Bromo-N-(5-methylpyrazin-2-yl)acetamide; tert-Butyl 5-methylpyrazin-2-ylcarbamate (2.4 g) was heated in hydrochloric acid (50 mL) at 50 C. for 30 min. The brown solution was cooled to RT and made basic by addition of solid sodium carbonate. The products were then extracted with ethyl acetate (2×100 mL) and dried over magnesium sulfate. Concentration of the extracts gave a crude solid. The solid was dissolved in dry DMF (30 mL) and cesium carbonate (11.21 g) added. To the stirred mixture was added bromoacetylbromide and the mixture stirred at RT for 2 h. Water (200 mL) was added, and the mixture extracted with ethyl acetate (2×100 mL). Concentration of the extract to 50 mL and addition of isohexane (100 mL) gave the subtitled compound as a solid (1.640 g).1H NMR (400 MHz, DMSO) delta 11.06 (1H, s), 9.17 (1H, s), 8.31 (1H, d), 4.16 (2H, s), 2.46 (3H, s).

The synthetic route of 369638-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ford, Rhonan; Mete, Antonio; Millichip, Ian; Teobald, Barry; US2010/113510; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1458-18-0, A common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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 2- (tributylstannyl) pyridine (1658.12 mg, 5.05 nMol, 2.00 equiv) , methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (500 mg, 2.525 nMol, 1 equiv) , Pd (PPh 3) 2Cl 2 (158.06 mg, 0.226 nMol, 0.1 equiv) and LiCl (190.94 mg, 5.05 nMol, 2 equiv) in 1, 4-dioxane (20 mL) was stirred for 16 hours at 90 under nitrogen atmosphere. This reaction was purification together with another batch E02189-006. The mixture was through a quick silica gel column chromatography, eluted with CH 2Cl 2 /MeOH (1: 1) to afford crude product. The resulting mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (CH 2Cl 2 /MeOH 30: 1) to afford methyl 3-amino-6-chloro-5- (pyridin-2-yl) pyrazine-2-carboxylate (180 mg, 30.20%) as a yellow solid. LCMS: m/z (ESI) , [M+H] + = 265.2. 1H NMR (300 MHz, DMSO-d 6) delta 3.9 (3H, s) , 7.5 (1H, ddd) , 7.6 -7.7 (2H, m) , 7.8 (1H, dt) , 8.0 (1H, td) , 8.7 (1H, ddd)

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, 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. Application In Synthesis of tert-Butyl (5-methylpyrazin-2-yl)carbamate

Step 2: 5-Methyl-2-aminopyrazine. To a stirred solution of (5-methyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (2.1 g, 10 mmol) in 30 mL CH2Cl2 at 0 C. under nitrogen was added trifluoroace (30 mL). The solution was allowed to warm to RT overnight. The solution was rotary evaporated to remove TFA and the residue was redissolved in 200 mL CH2Cl2 and stirred with 100 mL 10% Na2CO3. The organics were isolated and the aqueous solution extracted 3*100 mL with CH2Cl2. The organics were combined, dried (MgSO4), filtered and concentrated to an orange solid (1 g, 92%). 1H-NMR (400 MHz, CDCl3) delta8.46 (s, 1H), 7.70 (s, 1H), 2.49 (s, 3H).

The synthetic route of 369638-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem