Tag: M.W=200-300

The chemical industry reduces the impact on the environment during synthesis 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life. 1458-01-1

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 I) and NaOH (6 mol/l in water; 240 mL; 1 .44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 mL). Water (200 mL) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60¡ãC. Yield: 99.6 g (107percent of theory). C5H5ClN4O2. ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [M-H]-.

The chemical industry reduces the impact on the environment during synthesis 1458-01-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; BLUM, Andreas; HAMPRECHT, Dieter; KLEY, Joerg; WO2013/92674; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

13301-04-7,Some common heterocyclic compound, 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, molecular formula is C6H4Br2N2O2, 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 LiOH (121 mg, 5.07 mmol) in water (1 mL) was slowly added to a solution the pyrazine ester (500 mg, 1.67 mmol) in 1:1 THF/water (8 mL) at 0 C. After stirring at 0 C. for 45 min. The solvent was removed under reduced pressure. The residue was dissolved in a mixture of DCM and 1N aq. HCl. The organic layer was separated and the aqueous extracted twice with DCM. The combined organic extracts were dried (Na2SO4), filtered and concentrated to afford 350 mg (74%) of a cream colored solid. MS m/z (ES): 282 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,6-dibromopyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; de Vicente Fidalgo, Javier; Hermann, Johannes Cornelius; Lemoine, Remy; Li, Hongju; Lovey, Allen John; Sjogren, Eric Brian; Soth, Michael; US2011/59118; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1458-18-0, 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. 1458-18-0 name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, 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.

round bottomed flask was charged with methyl 6-amino 2,3-dichloro pyrazine 5-carboxylate (Aldrich, 25 g, 112.6 mmol), 2-S-ethyl piperazine (prepared as per Williams et al J. Med. Chem 1996, 39, 1345, 83% active, 15.7 g, 112.7 mmol), cesium carbonate (100 g, 300 mmol) and 1 ,4 dioxane (400 mL). The flask was equipped with a reflux condenser and heated to 8O0C. After 12hours the reaction was cooled, diluted with CH2CI2 (~ 200 mL), and filtered through celite. The filtrate was washed once with water and then concentrated to an oil. The crude product was purified by silica gel column chromatography (3% to 10% MeOH in CH2CI2) to afford compound A3 (30.8 g. 91 %). MS: M+H = 300

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/88836; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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. 1458-01-1.

Intermediate A. l : 3,5-Diamino-6-chloropyrazine-2-carboxylic acidA mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 1) and NaOH (6 mol/1 in water; 240 ml; 1.44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/1 in water; approx. 240 riiL). Water (200 ml) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60¡ãC.C5H5CIN4O2ESI Mass spectrum: m z = 189 [M+H]+; m z = 187 [M-H]~

The synthetic route of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KLEY, Joerg; HAMPRECHT, Dieter; HECKEL, Armin; (67 pag.)WO2016/113169; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life. 1458-18-0

To a suspension of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (IVa) (5.55 g, 25.0 mmol) in 2-propanol (50 mL) was added hexamethyleneimine (2.73 g, 3.1 0 mL, 27.5 mmol) and the mixture was stirred at room temperature. Diisopropyethylamine (3.55 g, 4.79 mL, 27.5 mmol) was then added and the reaction mixture was heated at reflux. After 2 h the reaction was allowed to cool to room temperature, which caused the product to crystallize. The solid product was collected by vacuum filtration and washed with cold 2-propanol followed by diethyl ether. After drying, the desired product (Ilia) was obtained as pink crystals (5.91 g, 83%).

The chemical industry reduces the impact on the environment during synthesis 1458-18-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY OF WOLLONGONG; KELSO, Michael; RANSON, Marie; BUCKLEY, Benjamin; ABOELELA, Ashraf; (103 pag.)WO2018/81863; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

32111-21-0, name is 2-Iodopyrazine, 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. 32111-21-0

2- (5- [1, 3] Dioxolan-2-yl-2, 4-dimethoxy-phenyl)-4, 4,5, 5-tetramethyl- [1, 3,2] dioxaborolane (Ex-12B, 2.22 g, 6.60 mmol, containing borolane impurity) was dissolved in DME (60 mL) and 2-iodopyrazine (0.59 mL, 6.0 mmol) was added. 2M aqueous NA2CO3 (17.8 ML, 35.6 mmol) was added and the mixture was purged with nitrogen for 20 min. Tetrakis (triphenylphosphine) palladium (0) (0.69 g, 0.60 mmol) was added and the mixture was heated at reflux for 2.5 h. After cooling, water (50 mL) was added and the mixture was extracted with CH2CI2 (2X30 mL). The organic phase was washed with brine (1X20 ML), dried over sodium sulfate, filtered, and concentrated. Purification of the resulting yellow-orange solids via silica chromatography (50-80% EtOAc/hexanes) provided 1.02 g OF 2- (5- [1, 3] dioxolan-2- yl-2, 4-dimethoxy-phenyl)-pyrazine as a yellow solid (59% YIELD).’H-NMR (CDCIS) 8 9.10 (d, J = 2 Hz, IH), 8.61 (m, 1H), 8.39 (d, J = 3 Hz, I H), 8.07 (s, I H), 6.57 (s, IH), 6.14 (s, 1H), 4.13-4. 18 (m, 2H), 4.01-4. 05 (m, 2H), 3.95 (s, 3H), 3.93 (s, 3H).

Statistics shows that 32111-21-0 is playing an increasingly important role. we look forward to future research findings about 2-Iodopyrazine.

Reference:
Patent; ATHEROGENICS, INC.; WO2004/56727; (2004); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

32111-21-0, The chemical industry reduces the impact on the environment during synthesis 32111-21-0, name is 2-Iodopyrazine, I believe this compound will play a more active role in future production and life.

Preparation 124: 2,4-Dimethoxy-5-pyrazin-2-yl-pyrimidine (Prep124); 2,4-Dimethoxy-pyrimidine-5-boronic acid (1.33 g, 7.27 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-iodo-pyrazine (1.0 g, 4.85 mmol), Na2CO3 (1.02 g, 9.70 mmol), PPh3 (127 mg, 0.48 mmol) and Pd(OAc)2 (54 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH- NH4OH (99-1-0.1 ) to give 481 mg of the title compound (45% yield).MS (ES) (mlz): 219.1 [M+H]*.

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

Reference:
Patent; Glaxo Group Limited; WO2007/113232; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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: 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 synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

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

1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, 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. 1458-01-1

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (40.0 g, 197 mmol), 2- [(E)-2-ethoxyethenyl]-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (84 ml, 400 mmol), SPhos (8.11 g, 19.7 mmol), palladium(ll) acetate (2.22 g, 9.87 mmol) and K3P04 (83.8 g, 395 mmol) in water:MeCN (2:3, 350 ml) was stirred at 80 ¡ãC for 2 h then allowed to cool to RT. The solid was collected by filtration then washed with EtOAc (100 ml) and water (100 ml) then dried in vacuo to afford the product as a brown solid (36.7 g, 76percent). 1 H NMR (500 MHz, DMSO-cfe) delta 7.15 (d, J = 12.2 Hz, 1 H), 6.79 (s, 4H), 5.97 (d, J = 12.2 Hz, 1 H), 3.91 (q, J = 7.0 Hz, 2H), 3.72 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H). LC/MS (System A): m/z (ESI+) = 239 [MH+], Rt = 0.88 min, UV purity = 98percent.

Statistics shows that 1458-01-1 is playing an increasingly important role. we look forward to future research findings about Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 1458-01-1 name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, 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. 1458-01-1

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 I) and NaOH (6 mol/l in water; 240 mL; 1 .44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 mL). Water (200 mL) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60¡ãC. Yield: 99.6 g (107percent of theory) ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [M-H]”

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HAMPRECHT, Dieter; HECKEL, Armin; KLEY, Joerg; WO2013/174757; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem