Tag: M.W=100-200

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. 98-97-5, name is Pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., 98-97-5

? Charged MeOH (8.8 L) and OT-1 (1758 g) at RT. (0129) ? Charged H2S04 (69.5 g) in one portion (21-22 C exotherm). Heated to (60-65 C) and stirred at 55-65 C for 19 hours. (0130) 19 h, 96.0% OT-2 and 4.0% OT-1 by HPLC (0131) ? Reaction was cooled to 15/30 C. No precipitate formed. (0132) ? NaHC03 (180 g) was charged in lots. The solution bubbled slightly and quickly went from yellow to pink. The mixture was stirred for 5 min at 15/30 C. (0133) ? The mixture was then concentrated to 1.5-2.5 vol at (0134) ? Charged NaCl (.700 g) in water (2.5 vol). Upon stirring, solution became clear. (0135) ? Stirred for 15 min at 15/30 C. After stirring, the aqueous layer became slightly cloudy. The solids were filtered off and the layers were separated. (0136) ? The aqueous layer was extracted with DCM (3×2 vol.). TLC indicated that extraction was complete after 3rd extraction. (0137) ? Organic layers were dried over anhydrous Na2S04 (.4g/g SM) . (0138) ? Concentrated to 1.5-2.5 vol under vacuum at (0139) ? Charged heptanes (8 vol) over a minimum of 30 min. Pale white slurry. Let stir overnight. ? Stirred at -5/- 15 C for a minimum of 1 hr. Solids were filtered off and rinsed with cold heptanes (0140) ? (2×1 vol.) Pulled solids dry on filter for 10 min. Dried in vacuum oven at (0141) Color changed, but no degradation was observed . (0142) Output material: ST-601 (0143) Lot No.: 2463-24- 1 (0144) Appearance: light Brown Solids (0145) Yield: 1721 g (91.0%) (0146) HPLC purity: 98.9% (0147) 1 NMR- Conforms to structure

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; ST IP HOLDING AG; FRAMROZE, Bomi P.; (65 pag.)WO2016/207914; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19745-07-4, 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. 19745-07-4, name is 2,5-Dichloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Description 6 1,1-Dimethylethyl 7-[(5-ch loro-2-pyrazi nyl)oxy]-1,2,4,5-tetrahyd ro-3H-3-benzazepi ne- 3-carboxylate (D6); 1,1-Dimethylethyl 7-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (182 mg, 0.69 mmol: obtainable by the process described in Description 3 from WO 02/40471) was dissolved in dry dimethylformamide (3 ml), cooled in an ice bath and treated with sodium hydride (60 percent in mineral oil, 29 mg, 0.72 mmol). The mixture was allowed to warm to room temperature over 1 hour. A solution of 2,5-dichloropyrazine (D5) (112 mg, 0.76 mmol) in dimethylformamide was added and the mixture stirred at room temperature for 2 hours and left to stand overnight under argon. The mixture was diluted with water and extracted with ethyl acetate (x 2). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated. The residue was purified by Biotage column chromatography, eluting with 1: 4 ethyl acetate: pentane to afford the title compound (208 mg). MS (ES+) m/e 376 [M+H]+.

The synthetic route of 2,5-Dichloropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/123723; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 5780-66-5, name is Pyrazine-2-carbaldehyde, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 5780-66-5

Intermediate 85 Ethyl 1-phenyl-3- [ (2-pyrazinylmethyl) amino]-1 H-pyrazole-4-carboxylate To ethyl 3-amino-1-phenyl-1H-pyrazole-4-carboxylate (250 mg, 1.08 mmol) was added DCM (6 mL), pyrazine-2-carboxaldehyde (233 mg, 2.16 mmol), acetic acid (0.18 mL, 3.24 mmol) and sodium triacetoxyborohydride (0.46 g, 2.16 mmol). The reaction was stirred overnight at room temperature, partitioned between DCM and water, passed through a hydrophobic frit and the organic layer concentrated. Purified by MDAP HPLC to give the title compound. MS calcd for (C17H17N5O2+H)+ : 324 MS found (electrospray) : (M+H) + = 324

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, 5780-66-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/92863; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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. 5521-58-4

Intermediate 19: 3-[(3S)-1-Methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)-5-phenylmethoxy-benzamide 1-Chloro-N,N,2-trimethyl-prop-1-en-1-amine (0.979 mL, 7.4 mmol) was added to a solution of 3-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-5-phenylmethoxy-benzoic acid (Intermediate 20) (2.1 g, 6.2 mmol) in DCM (50 mL) and stirred at ambient temperature for 50 minutes. 5-Methylpyrazin-2-amine (CAS no. 5521-58-4) (1.35 g, 12.4 mmol) and pyridine (1.0 mL, 12 mmol) were added and the reaction stirred for a further 3 hours. The solvent was evaporated under reduced pressure and the residue taken up in ethyl acetate (50 mL), washed with water (2*10 mL), brine (10 mL), dried (MgSO4) and filtered. Evaporation under reduced pressure gave crude product which was purified by flash chromatography on silica, eluding with a gradient of 0-100% ethyl acetate in isohexane. This crystallized to afford the product (449 mg, 17%). To the filtrate was added saturated sodium bicarbonate (20 mL) and the mixture extracted with 2:1 ethyl acetate:DCM (3*45 mL), the organics were washed with brine (10 mL), dried (MgSO4), filtered and evaporated under reduced pressure to give further product (937 mg, 35%). 1H NMR delta (300 MHz, CDCl3) 2.09-2.24 (m, 1H), 2.53-2.66 (m, 4H), 2.94 (s, 3H), 3.33-3.57 (m, 2H), 4.89 (t, 1H), 5.10 (s, 2H), 6.91 (s, 1H), 7.15-7.20 (m, 2H), 7.30-7.48 (m, 5H), 8.13 (s, 1H), 8.40 (s, 1H), 9.54 (s, 1H); m/z 433 (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 5521-58-4, its application will become more common.

Reference:
Patent; AstraZeneca AB; US2008/171734; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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. 113305-94-5

Svnthesis 1-1 -B5-(4-(4~Methoxybenzylamino)-5-nitropyridin-2-ylamino)pyrazine-2-carbonitrile A mixture of palladium (II) acetate (38 mg, 0.17 mmol) and (+/-)-2,2″- bis(diphenylphosphino)-1 ,1″-binaphthalene (318 mg, 0.51 mmol) a mixture of toluene and DMF (1 :1, 10 ml_) was degassed under a stream of nitrogen gas with stirring for 30 minutes. After addition of 2-amino-5-cyanopyrazine (245 mg, 2.04 mmol), sodium tert- butoxide (196 mg, 2.04 mmol) and N-(4-methoxybenzyl)-2-bromo-5-nitropyridin-4-amine (575 mg, 1.70 mmol), the mixture was degassed for a further 5 minutes and then heated at 140C for 30 minutes in a microwave reactor. Upon cooling, the mixture was diluted with methanol and isolated by SPE using 3 x 2.5 g MP-TsOH cartridges, washing with methanol and then eluting with 2 M ammonia in methanol. The basic fractions were concentrated in vacuo to give the title compound (470 mg, 1.25 mmol, 73%) which was used without further purification. LCMS (2) Rt = 2.18min; m/z (ESI-) 376 (M-H); (ESI+) 378 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 113305-94-5, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); 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. 120984-76-1, name is 2-Bromo-3-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 120984-76-1

A solution of C39 (2.35 g, 5.78 mmol), 2-bromo-3-methylpyrazine (1.0 g, 5.8mmol), [1 ,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (634 mg, 0.866mmol), and potassium carbonate (3.2 g, 23 mmol) in a mixture of 1,4-dioxane (30 mL) and water (8 mL) was stirred at 100 C for 2 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (Eluent: ethyl acetate) to afford the product as a yellow solid. Yield:0.90 g, 2.4 mmol, 42%. 1H NMR (400 MHz, CDCI3) oe 8.46(brd, J=2 Hz, 1H), 8.41 (d, J=2.6 Hz, 1H), 7.15 (d, J=8.2 Hz, 1H), 6.60 (dd, J=8.3, 2.3 Hz, 1H), 6.54 (d, J=2.3 Hz, 1H), 3.76 (5, 3H), 2.43 (5, 3H), 1.24-1.37 (m, 3H), 1.08-1.18 (m, 18H).

The synthetic route of 120984-76-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; ZHANG, Lei; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/162515; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6863-74-7, 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. 6863-74-7 name is 6-Chloropyrazine-2-carbonitrile, 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.

Example 1F (60 mg), 6-cyano-2-chloropyrazine (26 mg), KF (1 mg) and TEA (0.07 mL) were combined in a microwave tube and dissolved in ACN (2 mL). The reaction mixture was stirred in the micro wave oven at 130 C. for 1 h. The reaction mixture was filtrated and purified by preparative HPLC to yield an off-white solid (9 mg; 12%). MS: m/z=462.3 [M+H]+.

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

Reference:
Patent; Banner, David; Grether, Uwe; Haap, Wolfgang; Kuehne, Holger; Mauser, Harald; Plancher, Jean-Marc; US2012/115843; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-25-1, A common compound: 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Methyl 5-chloropyrazine-2-carboxylate (CAS no. 33332-25-1)(345.1 g) was dissolved in DMF (1.73 l). Lithium chloride (423.9 g) was added and the mixture heated to 140 C. over one hour. The mixture was evaporated, and the residue dissolved in water (3.4 l) by continued stirring. The solution was acidified by addition of 2N HCl (900 ml) and extracted into ethyl acetate (5¡Á1.73 l). The combined organic extracts were washed with water (2¡Á900 ml), brine (900 ml), dried (MgSO4), and evaporated to give the title compound (298.1 g). 1H NMR 6 (400.132 MHz, DMSO) 8.92 (d, 1H), 9.02 (d, 1H), 13.87 (s, 1H).

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, Methyl 5-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US2008/153800; (2008); 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. 19745-07-4, name is 2,5-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., 19745-07-4

Dissolved 2,5-dichloropyrazine (50 mg, 0.336 mmol), dicaesium(l+) carbonate (436 mg, 1.34 mmol), and (3S)-l,3-dihydrospiro[indene-2,4′-piperidin]-3-amine dihydrochloride (92.3 mg, 0.336 mmol, Intermediate I) in DMF (2 mL). The reaction mixture was stirred at 80 C for 3 h. The reaction mixture was then partitioned between EtOAc and water, and the aqueous layer was extracted 3 x with EtOAc. The organic layers were combined, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by column chromatography (0-10% MeOH in DCM w/ 1% NH4OH) to give (3S)-T- (5-chloropyrazin-2-yl)-l,3-dihydrospiro[indene-2,4′-piperidin]-3-amine (52.0 mg, 49% yield). LCMS m/z [M+H]+ = 315.4.

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; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

38557-72-1, 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. 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine, A new synthetic method of this compound is introduced below.

Step 1: Synthesis of 3,5-Dimethyl-2-(dibenzofuran-4-yl)pyrazine (abbreviation: Hdm4 dbfpr) First, into a recovery flask equipped with a reflux pipe were placed 1.51 g of 2-chloro-3,5-dimethylpyrazine, 2.25 g of 4-dibenzofuranylboronic acid, 1.12 g of sodium carbonate, 0.048 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the air inside the flask was replaced with argon. Heating was performed by microwave irradiation (2.45 GHz, 100 W) of this reaction container for 10 minutes, so that reaction occurred. After that, water was added to this reaction solution, and extraction with dichloromethane was carried out. A solution of the obtained extract was washed with water and dried over magnesium sulfate. After the drying, the solution was filtered. After the solvent of this solution was distilled, the obtained residue was washed with methanol, so that the pyrazine derivative which was the object of the synthesis, Hdm4 dbfpr, was obtained (a pale orange powder in a yield of 65%). Note that a microwave synthesis system (Discover, produced by CEM Corporation) was used for the microwave irradiation. The synthesis scheme of Step 1 is illustrated in the following scheme (x-1).

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; Semiconductor Energy Laboratory Co., Ltd.; US2012/104373; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem