Month: January 2021

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. category: Pyrazines

A solution of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (1.2 g, 5.92 mmol, 1.00 equiv) and 2-bromo-1,1-dimethoxyethane (2 g, 11.83 mmol, 2.00 equiv) in acetonitrile (20 mL) was irradiated with microwave for 40 min at 120¡ã C. After completion the resulting solution was concentrated under vacuum and the residue was purified by a silica gel column eluting with dichloromethane/methanol (10:1) to give the title compound (300 mg, 22percent) as a yellow solid. LC-MS (ES, m/z): 227 [M+H]+.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Tert-butyl 3-bromo-5l6-dihydro-[1 l2,4]tria2thetalo[4l3-a]pyrazine-7(8H)- carboxylate (202) (0.12 g, 0.4 mmol), m-fluorophenylboronic acid (70 mg, 0.5 mmol), Pd(PPh3)2CI2 (20 mg), K2CO3 (110 mg, 0.8 mmol) were mixed in a microwave reaction vial. The vial was capped and air was removed by vacuum through a needle, and back-filled with nitrogen (3 times). CH3CN (3 mL) and water (0.6 mL) was introduced via syringe. The mixture was then heated to 90 C for 10 h then diluted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated. The crude product was purified by flash chromatography to give compound 203 which was treated with 4 N HCl in dioxane at r.t. for 2 h to give the HCl salt.

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 723286-80-4.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline C.; ASLANIAN, Robert G.; CAO, Jianhua; CAPLEN, Mary Ann; CHAN, Tin-Yau; KIM, Hyunjin; KIM, Jae-Hun; KUANG, Rongze; LEE, Joe F.; WU, Heping; WO2010/59611; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 36070-80-1,Some common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

Oxalyl chloride (1.7 mL, 19 mmol) was added to a suspension of 5-chloropyrazine-2- carboxylic acid (CAS no. 36070-80-1) (2.53 g, 16.0 mmol) in dichloromethane (25 mL) and DMF (4 drops) at RT and under argon. The mixture was allowed to stir for 1.5h, concentrated in vacuo to and the residue was re-dissolved in dichloromethane (25 mL). Dimethylamine (2M in THF, 8.77 mL, 17.6 mmol) was then added dropwise followed by triethylamine (4.9 mL, 35 mmol) and allowed to stir for a further 5.5 hours. The reaction mixture was concentrated in vacuo and the residue was re-dissolved in dichloromethane and filtered. The filtrate was chromatographed on silica, eluting with a gradient of 50- 100% ethyl acetate in isohexanes to give the desired compound (1.88 g).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/50117; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

HATU (15.91 g, 41.8 mmol) was added to a stirred, cooled 0 C mixture of (6R,8aS)-3-oxooctahydroindolizine-6-carboxylic acid (7.3 g, 39.8 mmol), (3- chloropyrazin-2-yl)methanamine hydrochloride (7.89 g, 43.8 mmol) and DIPEA (10.44 ml, 59.8 mmol) in CH2C12 (25 ml) and the mixture was stirred at room temperature for 1 h. and then concentrated. The residue was purified by column chromatography on silica gel (Isco 240 g silica gel), eluting with CH2Cl2/MeOH (50/1) to give (6R,8aS)-N- ((3-chloropyrazin-2-yl)methyl)-3-oxooctahydroindolizine -6-carboxamide (11.15g, 36.1 mmol, 91 % yield) as a white solid. LC-MS: Ret. time 1.09 min; m/z 309.11 (M+H)+; 1HNMR (CDCI3, 500 Hz): 8.38 (1H, d, J = 2 Hz), 8.25 (1H, d, J = 2 Hz), 7.37 (1H, dd, J = 4 and 4.5 Hz), 4.56-4.72 (2H, m,l), 4.29 (1H, dd, J = 13 and 4.5 Hz),3.42-3.47 (m,l), 2.81 (1H, t, J = 13 Hz), 2.35 (2H, t, J = 8 Hz), 2.17-2.23 (1H, m), 2.04 (1H, d, J = 13.5 Hz), 1.94-1.96 (1H, m), 1.74-1.82 (1H, m), 1.55-1.62 (1H, m), 1.16-1.24 (1H, m).

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; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 345311-03-7, name is tert-Butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-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 345311-03-7, Product Details of 345311-03-7

7-Bromo-N-(3-ethyl-l-((6-methylpyridin-2-yl)methyl)-lH-indazol-4- yl)imidazo[l,2-a]pyridine-3-carboxamide (prepared as in Example 127, Step A; 50 mg, 0.10 mmol) in DMF (4 mL) was added tert-butyl 5,6-dihydroimidazo[l,2-a]pyrazine-7(8H)- carboxylate (68 mg, 0.31 mmol), Pd(PPh3) 4 (12 mg, 0.01 mmol), palladium diacetate (2.3 mg, 0.010 mmol) and K2C03 (42 mg, 0.31 mmol). The reaction mixture was purged with argon and the reaction vial was sealed and the mixture was heated to 140 C for 3 hours. The mixture was cooled to ambient temperature and diluted with DCM (20 mL). The solution was washed with H20, dried (Na2S04) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10: 1 :0.1) to provide the final product (14 mg). MS (ES+APCI) m/z = 532 (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, tert-Butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BRADLEY, Michael; DELISLE, Robert Kirk; HENNINGS, D. David; KENNEDY, April L.; MARMSATER, Fredrik P.; MEDINA, Matthew; MUNSON, Mark C.; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2011/79076; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 54013-07-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 54013-07-9 as follows.

Methyl 6-chloro-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate (26 mg, 0.084 mmol, prepared as described in Synthesis 62 and 63), 5-methoxypyrazin-2-amine (16 mg, 0.127 mmol), cesium carbonate (55 mg, 0.169 mmol), 4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene (3.9 mg, 7 mol%), and tris(dibenzylideneacetone)dipalladium chloroform complex (3.5 mg, 3.5 mol%) were added to a vial which was flushed with nitrogen and sealed. Anhydrous toluene (0.3 mL) and DMF (0.1 mL) were added and nitrogen was bubbled through the stirred solution for 10 minutes. The mixture was heated by microwave irradiation at 1300C for 30 minutes. The cooled solution was diluted with methanol and adsorbed onto an lsolute SCX-II column. The column was washed with methanol, then with 2M ammonia in methanol. The basic fractions concentrated. Preparative TLC, eluting with ethyl acetate – methanol – concentrated ammonia 10:1:0.2, gave methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3- ylamino)nicotinate (5 mg, 15%) as an oil.1H NMR (500 MHz, MeOH) delta 8.56 (1 H, s), 8.43 (1 H, s), 7.93 (1 H, s), 7.00 (1 H, s), 3.95 (3H, s), 3.84 (3H, s), 3.62-3.70 (2H, m), 2.60 (3H, s), 2.20-2.38 (4H, m), 2.00-2.10 (3H, m), 1.73-1.84 (2H, m). LCMS (3) Rt 1.70 min; m/z (ESI+) 399 (MH+).

According to the analysis of related databases, 54013-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 14508-49-7, 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. 14508-49-7 name is 2-Chloropyrazine, 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.

Step 1 To a solution of chloropyrazine (11.5 g, 0.1 mmol) in absolute ethanol (50 ml) was added anhydrous hydrazine (16 ml, 0.5 mmol) and the reaction mixture was refluxed for 3 h. The organics were removed in vacuo and the residue was extracted with benzene to give hydrazinopyrazine (4.2 g).

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

Reference:
Patent; Syntex (U.S.A.) LLC; US6316464; (2001); B1;,
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. 22047-25-2, name is Acetylpyrazine, A new synthetic method of this compound is introduced below., name: Acetylpyrazine

General procedure: Ketone (20 mmol) (2-acetylpyridine, 2-acetylthiazole or 2-acetylpyrazine)was added to a solution of aldehyde (10 mmol) (4-methoxybenzaldehyde,4-methoxy-1-naphthaldehyde or 6-methoxy-2-naphthaldehyde) in EtOH (75 mL). KOH (1.54 g, 27.5 mmol) and NH3(aq)(35 mL) were then added. The solution was stirred at room temp. for 24 h. The solid was collected by filtration and washed with H2O. Recrystallization from ethanol (L1,L4, L7) or toluene (L2, L3, L5, L6, L8,L9) afforded a crystalline solid.

The synthetic route of 22047-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Klemens, Tomasz; ?witlicka, Anna; Machura, Barbara; Kula, S?awomir; Krompiec, Stanis?aw; ?aba, Katarzyna; Korzec, Mateusz; Siwy, Mariola; Janeczek, Henryk; Schab-Balcerzak, Ewa; Szalkowski, Marcin; Grzelak, Justyna; Ma?kowski, Sebastian; Dyes and Pigments; vol. 163; (2019); p. 86 – 101;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 136927-64-5, name is 1-Chloropyrrolo[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 136927-64-5, Computed Properties of C7H5ClN2

Compound C4 (63.0 mg, 0.294 mmol), 1-chloropyrrolo[1,2-a]pyrazine (32.5 mg,0.21 mmol), and cesium carbonate (208 mg, 0.64 mmol) were combined in dimethylsulfoxide (1.0 mL), and the mixture was degassed with nitrogen for 5 minutes. After the reaction mixture had been heated to 120 C for 72 hours, it was cooled to room temperature, diluted with ethyl acetate, and filtered through diatomaceous earth. The filter pad was rinsed with ethyl acetate, and the combined filtrates were washed with 1:1water I saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered,and concentrated in vacuo. Purification using silica gel chromatography (Gradient: 0%to 5% methanol in dichloromethane) afforded the product as a white solid. Yield: 34 mg,0.10 mmol, 48%. LCMS m/z 331.1 [M+H]. 1H NMR (400 MHz, CDCI3) oe 9.00 (5, 1H),7.62 (d, J=4.8 Hz, 1H), 7.47-7.45 (m, 1H), 7.28-7.22 (m, 2H), 7.11-7.09 (m, 2H), 6.99-6.98 (m, 1H), 6.86-6.85 (m, 1H), 2.29 (5, 6H), 2.05 (5, 3H).

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; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
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. 274-45-3, name is Pyrrolo[1,2-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Pyrrolo[1,2-a]pyrazine

PREPARATION EXAMPLE 13 Preparation of 6-and 8-chloropyrrolo-[1,2-a]pyrazine 3.6 g of pyrrolo[1,2-a]pyrazine prepared in Preparation Example 1 was dissolved in a mixture of 20 ml of dimethyl sulfoxide and 20 ml of ethyl acetate; and 4.8 g of N-chloro succinimide was added thereto. The reaction mixture was stirred at 60 C. for 6 hours, poured into ice-water, extracted with ethyl acetate(100 ml*3), and then concentrated under a reduced pressure. The residue was chromatographed over silica gel to obtain 0.6 g of 6-chloropyrrolo[1,2-a]pyrazine and 0.4 g of 8-chloropyrrolo[1,2-a]pyrazine, respectively.

The synthetic route of 274-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yuhan Corporation; US5593984; (1997); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem