Month: July 2021

25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, 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 2,3-Dichloropyrido[2,3-b]pyrazine

To a solution of 2,3-dichloro-pyrido [2,3-b] pyrazine (0. 5G) in methanol was added 0.3N solution of sodium methoxide (6. 5ML). The resulting mixture was heated to reflux for 4 hours allowed to cool and used in example (7b)

The synthetic route of 25710-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/21513; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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. Application In Synthesis of 3,5-Dichloropyrazine-2-carbonitrile

To a solution of 44 3,5-dichloropyrazine-2-carbonitrile (3) (120mg, 0.69mmol) in 45 formamide (5.3g, 120mmol) were added 46 H2SO4 (37muL, 0.69mmol), FeSO4·7H2O (190mg, 0.69mmol) in 47 H2O (700muL) and 48 H2O2 (230muL, 2.1mmol) in H2O (700muL) dropwise at 0C, and the mixture was stirred at the same temperature for 30min. The reaction mixture was quenched with 49 ice water and extracted with EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water, saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to give 7 4 (99mg, 66%) as a pale yellow solid. 1H NMR (DMSO-d6) delta ppm 8.18 (1H, br s), 8.28 (1H, br s); MS (ESI) m/z 197, 199 [M-HCl+H2O]-

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 313339-92-3, its application will become more common.

Reference:
Article; Kunikawa, Shigeki; Tanaka, Akira; Takasuna, Yuji; Tasaki, Mamoru; Chida, Noboru; Bioorganic and Medicinal Chemistry; vol. 26; 20; (2018); p. 5499 – 5509;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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 313339-92-3, Recommanded Product: 3,5-Dichloropyrazine-2-carbonitrile

Example 34 5-(1-carbamoylcyclobutylamino)-3-(quinolin-6-ylamino)pyrazine-2-carboxamide A solution of 3,5-dichloropyrazine-2-carbonitrile (100 mg, 0.574 mmol), 1-aminocyclobutanecarboxamide hydrochloride (108 mg, 0.717 mmol) and DIEA (0.350 mL, 2.01 mmol) in DMF (4 mL) was stirred at room temperature for 70 h. Water and EtOAc were added. Organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 1-(6-chloro-5-cyanopyrazin-2-ylamino)cyclobutanecarboxamide (22 mg).

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; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 4774-14-5 as follows. Recommanded Product: 4774-14-5

EXAMPLE 5 2-amino-6-chloropyrazine 120 ml of water, 20.8 ml (0.31 mol, 4.6 eq) of an aqueous 28% ammonia solution and 10 g (0.067 mol, 1 eq) of 2,6-dichloropyrazine were successively added to an autoclave reactor. The autoclave was sealed and the mixture heated at 140 C. for 3 h, then left at room temperature for 60 h. The mixture was filtered, the precipitate washed with water, then vacuum dried. The reaction produced 5.4 g of a fine powder (yield: 63%). 1H NMR (CDCl3) delta (ppm): 7.88 (s, 1H, CH); 7.84 (s, 1H, CH); 4.68 (m, 2H, NH2). HPLC: t=1.07 min MS: 130 (MH+) HPLC purity: 100%

According to the analysis of related databases, 4774-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Maillet, Magali; Saniere, Laurent; Nicolai, Eric; Potin, Dominique; Langlois, Michel; US2005/267126; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(2R,5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-(hydroxymethyl) morpholine-4-carboxylate (2g, 4.12 mmol) was dissolved in 100 mL CH2Cl2and cooled to 0 C. TEMPO(0.13 g, 0.82 mmol) was added, followed by (diacetoxyiodo)benzene (2.65 g, 8.24 mmol). The ice bath was removed, and the reaction was allowed to warm to room temperature and stirred overnight. The mixture was diluted with 200 mL ethyl acetate and washed with 10% Na2S203, aq. satd. NaHC03, and brine. The organic phase was dried with Na2S04, filtered and concentrated to give (2R,5R)-4-(tert- butoxycarbonyl)-5 -(((tert-butyl diphenylsilyl)oxy)methyl)morpholine-2-carboxylic acid (1.36g, 66%). LCMS: [M-H]+:498.23 Ret. time= 1.33 min, LC-MS method E). Used as such for the next step without any further purification. (2R,5R)-4-(tert-butoxycarbonyl)-5-(((tert- butyldiphenylsilyl)oxy)methyl)morpholine-2-carboxylic acid (1.5g, 3.0 mmol) and (3- chloropyrazin-2-yl)methanamine. HC1 salt (0.54g, 3.0 mmol) were dissolved in DMF 100 mL. To the reaction mixture was added Et3N (0.76g, 6.0 mmol) followed by slow addition of HATU (1.37g, 3.6 mmol) at 0 C. The reaction was stirred at rt for 1 day under a stream of nitrogen and then quenched with sat. NaHC03 (100 mL) and extracted with EtOAc(2xl50 mL). The combined organic layer was washed with water(200 mL) , brine(200mL), dried over anhydrous Na2S04, filtered, and evaporated. The crude residue was subjected to column purification using 20-50%) EtO Ac/Hex. to give (2R,5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy) methyl)-2-(((3-chloropyrazin- 2-yl)methyl)carbamoyl)morpholine-4-carboxylate (0.86g, 46%). LCMS: [M-Boc +H]+:525.25 Ret. time= 2.74 min, LC-MS method E).

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, (3-Chloropyrazin-2-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

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

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. 41110-33-2, name is Methyl 5-methylpyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 5-methylpyrazine-2-carboxylate

5-Methyl-pyrazine-2-carboxylic acid methyl ester (1.60 g, 10.5 mmol; Macdonald, S. J. F. et al. J.Med.Chem. 2002, 45(18):3878-3890.), N-bromosuccinimide (5.62 g, 31.6 mmol), and dibenzoyl peroxide (0.255 g, 1.05 mmol) were dissolved in CCl4 (80 mL). The mixture was heated at reflux for 18 h. The reaction mixture was cooled and washed with 10% aq. Na2SO3 (2×20 mL) and H2O (1×30 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to yield a brown oily crude material (2.41 g). The crude product was purified (SiO2: 0-20% ethyl acetate/hexanes) to give the title compound (1.00 g, 31%).

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 41110-33-2.

Reference:
Patent; Carruthers, Nicholas I.; Shah, Chandravadan R.; Swanson, Devin M.; US2005/222151; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 313340-08-8, 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. 313340-08-8 name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, 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.

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (200 mg), 3-chloro-4-methylsulfonylaniline (374 mg) and NMP (1 mL) was stirred at 230 C. for 1 hour using a microwave reaction system. Thereafter, trans-4-aminocyclohexanol (524 mg) was added to the reaction liquid and stirred at 190 C. for 30 minutes using a microwave reaction system. After cooling, the reaction liquid was partitioned using ethyl acetate and water, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; chloroform_methanol=10:0 to 30:1) to give a crude product. This product was heated with ethanol and washed to give a light yellow solid. To the light yellow solid, ethyl acetate was added and heated, and insoluble materials were separated by filtration and the filtrate was concentrated. After the filtrate was concentrated, the residue was heated and washed with ethanol to give 3-{[3-chloro-4-(methylsulfonyl)phenyl]amino}-6-ethyl-5-[(trans-4-hydroxycyclohexyl)amino]pyrazine-2-carboxamide (39 mg) as a light yellow solid.

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

Reference:
Patent; Waters Technologies Corporation; US2012/40968; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 870787-06-7,Some common heterocyclic compound, 870787-06-7, name is 3-(Trifluoromethyl)pyrazine-2-carboxylic acid, molecular formula is C6H3F3N2O2, 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 compound (2 mmol) represented by the formula (2-1) was added to a 100 mL round bottom flask.EDCI (2.4 mmol), HOBt (2.4 mmol) and 10 mL of DMF were reacted at 25 C for 1 h.Then, the compound represented by formula (2-21) or formula (2-22)(2.4 mmol) was added to the above solution,Reaction at 25 C for 24 h,After removing the solvent, column chromatography gave the desired product (yield of the desired product as a one-step yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)pyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; Central China Normal University; Yang Guangfu; Li Hua; Xiong Li; (10 pag.)CN109666004; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 36070-79-8, 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. 36070-79-8, name is 6-Chloropyrazine-2-carboxamide belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 6-chloropyrazine-2-carboxamide (75 mg, 0.47 mmol) and (2- (methylthio)benzo[djthiazol-6-yl)methanamine (50 mg, 0.24 mmol) in DMA (475 .il) was added DIEA (46 pi, 0.26 mmol) and the resulting mixture was stirred at 120 C for 2 h. The mixture was concentrated. The residue was purified via silica gel chromatography (0 – 10 % MeOH in DCM with 0.2% NH4OH) to give the title compound (43 mg, 55%) as a tan solid. MS (ES+) C,4H,3N5052 requires: 331, found: 332 [M+Hf?. ?H NMR (500 MHz, DMSO-d6)oe 8.22 (s, 1H), 8.13 (s, 1H), 8.02 (s, 1H), 7.94 – 7.89 (m, 2H), 7.80 (d, J= 8.4 Hz, 1H), 7.61 (s, 1H), 7.48 (d, J= 9.5 Hz, 1H), 4.72 (d, J 5.8 Hz, 2H), 2.78 (s, 3H)

The synthetic route of 6-Chloropyrazine-2-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TESARO, INC.; JONES, Philip; CZAKO, Barbara; BURKE, Jason P.; CROSS, Jason; LEONARD, Paul Graham; (208 pag.)WO2018/81276; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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. SDS of cas: 313339-92-3

(4-tert-Butoxycarbonyl-aminophenyl)boronic acid pinacol ester (8.26 g) was added to a reaction vessel containing a magnetic stirring bar together with 3,5-dichloro- pyrazine-2-carbonitrile (5.0 g), 1,1 ?-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (1.68 g) and cesium carbonate (28.1 g), followed by 100 ml dioxane and 10 ml water, and the mixture heated to 100 00 under stirring. After 1 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (100 ml) and extracted with EtOAc (3 x 200 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated to afford the crude product as a brown oil which was purified by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent. The obtained product was recrystallized from methyl tert-butyl ether to afford [4-(6-chloro-5-cyano-pyrazin-2-yl)-phenyl]-carbamic acid tert-butyl ester as a pale yellow solid after drying under vacuum. Yield: 6.92 g (73%).

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; NAZARE, Marc; HALLAND, Nis; SCHMIDT, Friedemann; WEISS, Tilo; DIETZ, Uwe; HOFMEISTER, Armin; WO2013/41502; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem