Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 486424-37-7, name is 3-Amino-6-bromopyrazine-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 486424-37-7, name: 3-Amino-6-bromopyrazine-2-carboxylic acid

Example 5 : 3-Amino-6-(3-hydroxy-3-methyl-but-l-ynyl)-N-phenyl-pyrazine-2- carboxamide (Compound 11-81)SCHEME VSteps 1 to 2Compound 11-81METHOD E:Step 1: 3-Amino-6-bromo-N-phenylpyrazine-2-carboxamide[00151] A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (3.5 g, 16.05 mmol), l,l’-carbonyldiimidazole (5.205 g, 32.10 mmol), DIPEA (2.282 g, 3.075 mL, 17.66 mmol) and DMAP (98.04 mg, 0.8025 mmol) were combined in DMSO (131 mL) and stirred for 30 min. Aniline (1.495 g, 1.463 mL, 16.05 mmol) was then added and the resulting solution stirred at ambient tempaerture for 18 hours. After this time water was added and the product collected by filtration to give a brown powder (3.5 g, 74% Yield).1H NMR (400.0MHz, DMSO) delta 7.04 (1H, m), 7.29 (2H, m), 7.72 (4H, m), 8.36 (1H, s), 10.22 (NH2) ppm; MS (ES+) 295.

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; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 36070-84-5, name is 5-Bromopyrazine-2-carboxamide, molecular formula is C5H4BrN3O, 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. Safety of 5-Bromopyrazine-2-carboxamide

Step 2: [6-(5-Carbamoyl-pyrazin-2-yloxy)-l-hydroxy-4-methyl-l, 3-dhydro- benzo[c] [ 1 ,2] oxaborol-3-yl] -acetic acid ethyl ester[0615] A suspension of (1 ,6-dihydroxy-4-methoxymethyl-l ,3-dihydro- benzo[c][l,2]oxaborol-3-yl)-acetic acid ethyl ester (150 mg, 0.600 mmol) and CS2CO3 (430 mg, 1.32 mmol) in DMF (4 mL) was treated with 5-bromo-pyrazine-2- carboxylic acid amide (158 mg, 0.780 mmol) at room temperature and the reaction was heated to 80 0C for 2 h. The reaction mixture was concentrated to dryness. The residue was diluted with water and adjusted to pH 2 with IN HCl. The aqueous phase was extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate = 1 :2 to DCM/MeOH = 10: 1) to afford the title compound as a white solid (110 mg). 1H NMR (300 MHz, CD3OD) delta 8.90 (s, IH), 8.34 (s, IH), 7.48 (s, IH), 7.35 (s, IH), 7.08 (s, IH), 5.70 (s, IH), 5.69-5.66 (m, IH), 4.21 (q, 2H), 3.14-3.12 (m, IH), 2.49-2.41 (m, IH), 2.37 (s, 3H), 1.26 (t, IH). MS found: (M+H)+ : 372.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36070-84-5, its application will become more common.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; GLAXOSMITHKINE LLC; XIA, Yi; ALLEY, Michael, Richard Kevin; ZHOU, Yasheen; SINGH, Rajeshwar; DING, Charles; CAO, Kathy; PLATTNER, Jacob, J.; OU, Ligong; JIA, Guofeng; SARASWAT, Neerja; RAMACHANDRAN, Sreekanth; ZHOU, Ding; WO2011/17125; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 32111-21-0, A common heterocyclic compound, 32111-21-0, name is 2-Iodopyrazine, molecular formula is C4H3IN2, 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.

Example 47; S-fS^-Chloro-phenyl^-oxo–^-pyrazin-?-yl-pheny?^.S-dihvdro-pyrazolorB^-dipyrimidin- 1 -yll-benzonitrile; [00175] A solution of 3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4 ,4,5,5-tetramethyl-[l ,3,2]- dioxaborolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-l-yl}-benzonitrile (prepared as described in example 28, 3.6 g, 6.54 mmol) in N,N-dimethylformamide (70 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (2.0 g, 9.82 mmol), cesium carbonate (4.2 g, 13.09 mmol), Pd(dppf)2Cl2 (0.53 g, 0.654 mmol) is added and the resulted mixture is degassed with argon for 0.5 h The reaction mixture is then heated at 100 0C for 1.5 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3 x). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by column chromatography to afford 3-[5-(4-chloro-phenyl)-4-oxo-6-(4-pyrazin-2- yl-phenyl)-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-l-yl]-benzonitrile. 1H NMR (DMSO-dbeta, 400 MHz) delta 9.25 (s, IH), 8.71 (m, IH), 8.62 (m, 2H), 8.51 (m, 2H), 8.08 (d, 2H), 7.90 (m, IH), 7.88 (m, IH), 7.60 (d, 2H), 7.44 (m, 4H); LC-MS calculated for C28H16ClN7O (M+H+) 502.1, found 502.0.

The synthetic route of 32111-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 143591-61-1,Some common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, molecular formula is C6H3BrClN3, 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.

Example 13 – N-fS-fS-fCvclohexylamino^midazop^-alpyrazin-S-ypphenvpacetamide (Compound 165)[00260] 3-Bromo-8-bromo/chloroimidazo[l,2-a]pyrazine (200 mg, 0.86 mmol) was combined with JV,iV-diisopropylethylamine (750 uL, 4.3 mmol), cyclohexylamine (1.97 mL, 17.2 mmol) and THF (4 mL) and the mixture heated in a sealed tube at 7O C for 16 hours. In a separate reaction, 3-bromo-8-chloroimidazo[l,2-a]pyrazine (200 mg, 0.86 mmol) was combined with N,N-diisopropylethylamine (750 uL, 4.3 mmol), cyclohexylamine (0.49 mL, 4.3 mmol) and THF (4 mL) and the mixture heated in a sealed tube at 7O C for 16 hours. The reactions were worked up separately. Upon cooling, the reaction mixtures were partitioned between DCM and water and the orgranic extract washed with water and brine, dried over MgSO4, and concentrated in vacuo. The crude products were then combined and purified by column chromatography (EtO Ac/petroleum ether) to give 3-bromo-N-cyclohexylimidazo [l,2-a]pyrazin-8-amine (372 mg, 73%). LCMS RT= 1.66min, MH+ 296.9. 1U NMR (d6- DMSO): 7.45-7.47 (2H, m), 7.38 (IH, d, J4.8), 5.85-7.87 (IH, m), 4.10 (IH, m), 2.10-2.16 (2H, m), 1.77-1.84 (2H, m), 1.62-1.72 (IH, m), 1.26-1.52 (5H, m).

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-8-chloroimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); 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: 5-Bromo-3-chloropyrazin-2(1H)-one

4.3.20 3,5-Bis-(4-methoxyphenyl)-1H-pyrazin-2-one 57 A solution of 56 (50.6 mg, 0.242 mmol), sodium carbonate (35.6 mg, 0.336 mmol), 4-methoxyphenylboronic acid (182 mg, 1.20 mmol) and tetrakis(triphenylphosphine)palladium (0) (17 mg, 0.015 mmol) in water (0.7 mL) and acetonitrile (2.7 mL) was heated in a microwave reactor using variable wattage to 150 C for 20 min. The mixture was partitioned between ethyl acetate (50 mL) and water (40 mL). The organic layer was filtered through a plug of silica gel (6 g). The filtrate was concentrated and purified by flash column chromatography on silica, eluting with ethyl acetate to give 57 (73 mg, 47%). Mp >300 C; Rf (EtOAc) 0.16; numax (thin film/cm-1) 3019 (Ar CH), 1653 (C=O), 972 (C-O), 929 (C–O); deltaH (500 MHz; CD3OD) 3.85 (3H, s, OCH3), 3.88 (3H, s, OCH3), 7.01 (2H, d, J 8.0 Hz, ArH), 7.02 (2H, d, J 9.0 Hz, ArH), 7.66 (1H, s, 6-H), 7.86 (2H, d, J 8.0 Hz, ArH), 8.46 (2H, d, J 9.0 Hz, ArH); LC-MS (6 min) m/z 309 (MH+); HPLC tR 4.11 min; purity 99%; HRMS (found: m/z 309.1243; C18H17N2O3 requires 309.1234).

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

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. Computed Properties of C7H3Cl2N3

(D) (S)-1 -(1 -(7-chloropyrido[4,3-ib]pyrazi n-5-yl)pyrrolidi n-3-yl)ethanol .[01 60] (S)-teri-butyl 3-(1 -hydroxyethyl)pyrrolidine-1 -carboxylate was treated with HCI solution (in EtOAc, 5 mL) at room temperature for 2 hours . The volatiles were removed under reduced pressure, and the residue was dissolved in anhydrous THF (10 mL). To the resulted THF solution, DIPEA (570 mg, 4.4 mmol) and 5,7- dichloropyrido[4,3-?>]pyrazine (400 mg, 2.0 mmol) were added, and the reaction was stirred at room temperature overnight. The volatiles were removed under reduced pressure, and the residue was dissolved in ethyl acetate, washed with brine and dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography to afford the title compound. MS (m/z): 279 (M+H)+.

The synthetic route of 1379338-74-5 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. 32111-21-0, name is 2-Iodopyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H3IN2

Example 59; 3-fl-f4-Chloro-phenyl’)-6-oxo-2-(‘4-pyrazin-2-yl-phenv?-.6-dihvdro-purin-9-yll-benzene sulfonamide; [00194] A solution of 3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-l-yl}-benzene sulfonamide (prepared as described in example 25, 0.500 g, 0.82 mmol) in N,N- dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.250 g, 1.24 mmol), cesium carbonate (0.530 g, 1.65 mmol), Pd(dppf)2Cl2 (0.06 g, 0.08 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 50 0C for 12 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3*). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and’ purified by column chromatography over silica gel (60 – 120 mesh) to afford 3-[l-(4-chloro-phenyl)-6-oxo-2-(4-pyrazin-2-yl-phenyl)-l,6-dihydro-purin- 9-yl]-benzene sulfonamide. 1H NMR (DMSO-dbeta, 400 MHz) delta 9.24 (m, IH), 8.69 (m, IH), 8.63 (m, IH), 8.30 (m, IH), 8.02-8.08 (m, 2H), 7.94 (m, IH), 7.82 (m, IH), 7.43-7.58 (m, 8H), 7.15 (br, 2H); LC-MS calculated for C27H18ClN7O3S (MH-H+) 556.1, found 555.9.

The synthetic route of 32111-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 21943-17-9,Some common heterocyclic compound, 21943-17-9, name is 5-Bromo-3-chloropyrazin-2(1H)-one, molecular formula is C4H2BrClN2O, 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: 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-3-chloropyrazin-2(1H)-one, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)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 1196152-38-1, Safety of 2-Bromo-5-(trifluoromethyl)pyrazine

To a solution of ethyl 2-hydroxyacetate (0.167 mL, 1.762 mmol) in tetrahydrofuran (4 mL) at room temperature was added potassium teri-butoxide (1.850 mL, 1.850 mmol). After 10 minutes, 2-bromo-5-(trifluoromethyl)pyrazine (0.2g, 0.881 mmol) in tetrahydrofuran (4 mL) was added. The mixture was stirred at room temperature overnight. The reaction mixture was quenched by addition of water (10 mL), and extracted with ethyl acetate (3 x 30 mL). The organic phase was dried with MgSO/t, filtered and concentrated under reduced pressure. The residue was used in the next step without further purification (215 mg, 0.859 mmol, 98% yield).JH NMR (400 MHz, DMSO-19F NMR (376 MHz, DMSO- 6) delta ppm -65.37 MS (ESI+) m/z 251 (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-Bromo-5-(trifluoromethyl)pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486424-37-7, name is 3-Amino-6-bromopyrazine-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 486424-37-7, Recommanded Product: 3-Amino-6-bromopyrazine-2-carboxylic acid

HATU (3.54 g, 9.36 mmol) was added to a solution containing 1.64 g (7.5 mmol) of 3-amino-6-bromopyrazine-2-carboxylic acid in 25 mL of DMF. The reaction was stirred for 5 minutes before adding 2.5 mL (22.5 mmol) of N-methylmorpholine and 1.68 g (9.36 mmol) of 4-morpholinopyridin-3-amine. The reaction mixture was stirred for 16 h then quenched with 10 mL of saturated NH4C1 solution and then 10 mL of water. The mixture was extracted with EtOAc three times; the combined organics were washed with brine and then dried over Na2S04. The solvent was then evaporated and the residue was chromatographed (0% to 20% CH3OH / dichloro methane) to afford compound Int lB-1 as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Amino-6-bromopyrazine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SILVERBACK THERAPEUTICS, INC.; THOMPSON, Peter Armstrong; EDRIS, Badreddin; COBURN, Craig Alan; BAUM, Peter Robert; ODEGARD, Valerie; (277 pag.)WO2018/227018; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem