Month: November 2020

6270-63-9, 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. 6270-63-9 name is Pyrazin-2(1H)-one, 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 5 In analogy to example 1C, (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester (example 1B) was reacted with 1-(4-amino-3-fluoro-phenyl)-1H-pyrazin-2-one (prepared from 2-fluoro-4-iodoaniline by reaction with 1H-pyrazin-2-one, Cu(I)I, N,N’-dimethylethylenediamine and cesium carbonate in dioxane at 120 C.) to give 5-chloro-thiophene-2-carboxylic acid {(1S,2S,4R)-4-[2-fluoro-4-(2-oxo-2H-pyrazin-1-yl)-phenylcarbamoyl]-2-hydroxy-cyclopentyl}-amide. Yellow solid. MS: 477.0 ([M+H]+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrazin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Zbinden, Katrin Groebke; Haap, Wolfgang; Hilpert, Hans; Panday, Narendra; Ricklin, Fabienne; US2007/49587; (2007); 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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., 1458-18-0

To a stirred mixture of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (50 mg, 0.225 nMol, 1 equiv) and DIEA (87.31 mg, 0.676 nMol, 3 equiv) in DMSO was added morpholine (39.24 mg, 0.450 nMol, 2 equiv) in portions at room temperature . The resulting mixture was stirred for overnight at room temperature . The reaction was quenched with Water at room temperature. The precipitated solids were collected by filtration and washed with water (1×100 mL) , dried under vacuum to afford methyl 3-amino-6-chloro-5- (morpholin-4-yl) pyrazine-2-carboxylate (1.8 g, 97.71%) as a yellow solid. 1H-NMR (400 MHz, Chloroform-d) delta 3.61 -3.72 (4H, m) , 3.75 -3.88 (4H , m) , 3.94 (3H, s) .

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; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-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 1458-01-1, 1458-01-1

3,5-Diamino-6-chloropyrazine-2-carboxylic acid A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 l) 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¡ã C. C5H5ClN4O2 ESI Mass spectrum: m/z=189 [M+H]+; m/z=187 [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, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KLEY, Joerg; FRATTINI, Sara; HAMPRECHT, Dieter; HECKEL, Armin; US2015/18313; (2015); 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

5049-61-6, 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. 5049-61-6 name is Pyrazin-2-amine, 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 solution of 2-aminopyrazine 4 (3.81 g, 40.1 mmol) in DMSO (80 mL) and water (2 mL) was stirred at 0 C for 10 min. NBS (16.4 g, 92.2 mmol) was added portionwise to the solution over 50 min, keeping the temperature below 15 C. The reaction mixture was warmed to rt and stirred for 16 h. The solution was poured into ice-water (250 mL) and stirred. The orange solid was collected by filtration and dried. The filtrate was extracted with ethyl acetate (200 mL). The organic layer was washed with 5% aqueous sodium carbonate (50 mL) and water (50 mL), then dried, filtered and concentrated. The combined material was recrystallised from water (200 mL) to give 5 (7.80 g, 77%) as a brown solid. (Found: C, 19.33; H, 1.10; N, 16.68; C4H3N3Br2 requires C, 19.00; H, 1.20; N, 16.62%); deltaH (250 MHz; CDCl3) 5.08 (2H, br s, NH2), 8.07 (1H, s, 6-H); deltaC (125 MHz; CDCl3) 123.7, 123.9, 143.2, 151.9; LC-MS (15 min) m/z 256, 254, 252 (MH+); HPLC tR 4.45 min; purity 98%; (HRMS found: MH+ m/z 251.8776; requires 251.8766).

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

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

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

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

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

6270-63-9, 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. 6270-63-9 name is Pyrazin-2(1H)-one, 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.

Using the same procedure described in example 1 using 1-(4-amino-3-fluoro-phenyl)-1H-pyrazin-2-one (prepared from 2-fluoro-4-iodoaniline by reaction with 1H-pyrazin-2-one, Cu(I)I, N,N’-dimethylethylenediamine and cesium carbonate in dioxane at 120 C.), the title compound was obtained as a white solid (15 mg). MS: 508.0 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrazin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer, Markus; Zbinden, Katrin Groebke; Haap, Wolfgang; Hilpert, Hans; Panday, Narendra; Ricklin, Fabienne; US2007/15812; (2007); 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. 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