Tag: M.W=100-200

Reference of 54013-07-9, 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. 54013-07-9 name is 5-Methoxypyrazin-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.

Example 1AX; Preparation of 2-ethyl-N-(5-methoxypyrazin-2-yl)-4-f4- (methylsulfonyl)phenoxyl-2H-indazole-6-carboxamide (1AX): To a solution of 5-methoxypyrazin-2-annine (167 mg, 1.34 mmol) in dry dichloroethane (2.0 ml_) was added dimethylaluminum chloride (2.67 ml_, 2.67 mmol) slowly at O0C under nitrogen. After addition, the mixture was stirred for 1 hour at room temperature and then added methyl 2-ethyl-4-(4- (methylsulfonyl)phenoxy)-2H-indazole-6-carboxylate (1-1 f-7,100.0 mg, 0.267 mmol). Then the mixture was heated to 60-700C overnight. The reaction mixture was cooled to room temperature, poured into potassium sodium tartrate (aq., 10 ml_), and extracted with ethyl acetate (10 ml_ 3 times). The combined organic layers were dried and concentrated under reduced pressure and purified by preparative HPLC to afford the title compound (1AX, 20.0 mg, yield: 16%) as a white solid.1H NMR (400 MHz, DMSO-d6): delta 1.46-1.49 (t, 3H), 3.15 (s, 3H), 3.88 (s, 3H), 4.43-4.49 (q, 2H), 7.20 (s, 1 H), 7.17-7.31 (d, 2H), 7.91 -7.93(d, 2H), 8.15(s, 1 H), 8.32(s, 1 H), 8.44 (s, 1 H), 8.88 (s, 1 H), 10.97 (s, 1 H). MS (M+1 ): 468.2.

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

Reference:
Patent; PFIZER INC.; CORBETT, Jeffrey Wayne; GUZMAN-PEREZ, Angel; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/103438; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 36070-79-8,Some common heterocyclic compound, 36070-79-8, name is 6-Chloropyrazine-2-carboxamide, molecular formula is C5H4ClN3O, 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: 150 mg (0.952 mmol) of 5-Cl-PZA (1) or 6-Cl-PZA (2) was dissolved in ethanol together with triethylamine (1 eq., 96 mg, 0.952 mmol). Three equivalents of corresponding alkylamine were added to the reaction mixture and refluxed in ethanol generally for 6 hours. The completion of the reaction was checked by TLC chromatography (eluent: hexane/ethyl acetate, 1:2). The crude product was absorbed on silica by solvent evaporation and purified by flash chromatography (hexane/ethyl acetate gradient elution).

The synthetic route of 36070-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Servusova, Barbora; Paterova, Pavla; Mandikova, Jana; Kubicek, Vladimir; Kucera, Radim; Kunes, Jiri; Dolezal, Martin; Zitko, Jan; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 450 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 36070-80-1, 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

5-chloropyrazine-2-carboxylic acid (15.0g) and ethyl acetate (200 ml) solution which is prepared by mixing, is reacted with a thionyl chloride (30 ml) and N,N-dimethylformamide (0.28 ml), was stirred at 55 C to 60 C for 1 hour. Concentrated within a pressure reduced to reaction mixture, by the addition of toluene concentrating operation was performed 2 times. 4-[4-methoxy-3-(trifluoromethyl)phenyl]-1,3-thiazole-2-amine (19.96g) and cyclopentylmethyl ether (200 ml) were mixed, to this mixture the residue obtained above in cyclopentylmethyl ether (40 ml) was added dropwise at 10 C or lower, and the reaction mixture was warmed to room temperature and stirred for 5 hours. And round the leucorrhea reaction mixture, water (600 ml) for 15 C hereinafter in the dropped at room temperature the laststraw stirring section. Taking out a solid filtering, drying the adhesive after cleaning the front and back methyl ethyl ketone 5-chloro-N-{4-[4-methoxy-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}pyrazine-2-carboxamide (29g) obtained as solid.

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

Reference:
Patent; Astellas Pharma Co. Ltd.; Takahashi, Daisuke; Maeda, Jun; Inakaki, Yusuke; Nekoro, Genji; Tanaka, Hiroaki; Yokoyama, Katsuhiro; Takamitsu, Hajime; Koike, Takanori; Tsukamoto, Itsei; (153 pag.)KR2015/120516; (2015); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 22047-25-2, The chemical industry reduces the impact on the environment during synthesis 22047-25-2, name is Acetylpyrazine, I believe this compound will play a more active role in future production and life.

(1) the isoniazid (1.64g, 12mmol), 2 – acetyl pyrazine (1.46g, 12mmol), 1.0 ml of formic acid is dissolved in 60 ml ethanol, reflux reaction 4h, cooling to room temperature, the generating precipitation filtering, cold washing with ethanol, to obtain white solid isoniazid compression acetyl pyrazine 2.75g, yield: 95%

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, Acetylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qin, Jie; Ren, Qingling; Zhao, Shanshan; Liu, Yaping; Liu, Yanfei; Zhang, Keke; Zhu, Hailiang; (9 pag.)CN105061475; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 14508-49-7, 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 14508-49-7 as follows.

General procedure: 2,6-dichloropyrazine (10.49 g, 70.38 mmol) was dissolved in 150 mL of ethanol. After stirring for 5 min, 80% hydrazine hydrate (7.05 g, 0.147 mol) was added. The reaction was heated to 80 C and refluxed for 10 h until the solution became clear. The resulting mixture was cooled to room temperature, and a yellow solid was precipitated. The suspension was filtered, and the filtrate was concentrated under reduced pressure to afford a yellow solid 9.1 g.

According to the analysis of related databases, 14508-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Weijie; Li, Jiao; He, Kai; Huang, Fangfang; Ma, Yi; Li, Yuxin; Li, Qingshan; Xu, Fengbo; Chinese Chemical Letters; (2019); p. 417 – 420;,
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 22047-25-2 as follows. Recommanded Product: 22047-25-2

The synthetic procedure used in this preparation is outlined below in Scheme D. To a solution of 1-pyrazin-2-yl-ethanone (2.0 g, 15.85 mmol) and ammonium acetate (19.337 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 11.1 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH=13. The aqueous solution was extracted with dicholromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 14.62 g of 1-pyrazin-2-yl-ethylamine, yield: 75%. MS (M+H)=124.

According to the analysis of related databases, 22047-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Broka, Chris Allen; Hawley, Ronald Charles; US2010/324056; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, 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. SDS of cas: 68774-77-6

A mixutire of (0.070 g, 0.13 mmol), 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (0.020 g, 0.13 mmol) and sodium carbonate monohydrate (0.016 g, 0.13 mmol) in ethanol (2 mL) and dimethylformamide (2 mL) was heated at 45 C. for 4 days. The mixture was brought to RT, concentrated, and the residue was dissolved in ethyl acetate. The organic phase was washed with water, brine, dried over MgSO4, filtered, concentrated, and purified by HPLC to afford (2R,3,S)-3-([1,2,4]triazolo[4,3-a]pyrazin-8-ylamino)-4-(3,5-difluorophenyl)-1-((R)-2,2-spirocyclobutane-6-neopentyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine-4-ylamino)butan-2-ol as a light yellow solid. MS m/z: 577.8 (M+1).

The synthetic route of 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US2010/120774; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33332-25-1, name is Methyl 5-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 33332-25-1, Product Details of 33332-25-1

Intermediate 33: 5-Chloropyrazine-2-carboxylic acid To a solution of methyl-5-chloropyrazine-2-carboxylate (120 mg, 0.70 mmol) in a mixture of acetonitrile (2 mL) and DMF (1 mL) was added lithium chloride (295 mg, 6.95 mmol). The suspension was heated to 160 C. for 5 minutes in a microwave after which time the reaction was diluted with water (10 mL). Saturated sodium bicarbonate solution (20 mL) was added and the aqueous layered extracted with ethyl acetate (2*30 mL). The organic extracts were discarded and the aqueous layer adjusted to pH 4 with 1N hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate (20 mL) and the combined organics washed with water (2*20 mL) and brine (10 mL) and dried (MgSO4). The volatiles were removed under reduced pressure to afford the product (68 mg). 1H NMR delta (400 MHZ, CDCl3): 7.20 (1H, br s), 8.72 (1H, s), 9.21-9.21 (1H, m); m/z 157 (M-H)+.

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

Electric Literature of 4745-93-1, The chemical industry reduces the impact on the environment during synthesis 4745-93-1, name is 5H-Pyrrolo[2,3-b]pyrazine, I believe this compound will play a more active role in future production and life.

Example 4; Synthesis of propane-1-sulfonic acid [2,4-difluoro-3-(5H-pyrrolo[2,3-b]pyrazine-7-carbonyl)-phenyl]-amide P-0001; Propane-1-sulfonic acid [2,4-difluoro-3-(5H-pyrrolo[2,3-b]-pyrazine-7-carbonyl)-phenyl]-amide P-0001 was prepared in two steps from 5H-pyrrolo[2,3-b]pyrazine 3 as shown in Scheme 2.; Step 1-Preparation of propane-1-sulfonic acid 2,4-difluoro-3-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-phenyl-amide (9); To 5H-pyrrolo[2,3-b]pyrazine (3, 0.150 g, 1.26 mmol) and propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (8, 0.388 g, 1.47 mmol), 2.2 mL of methanol was added. This suspension was allowed to stir for 10 minutes, followed by the addition of potassium hydroxide (0.230 g, 4.10 mmol). The reaction was allowed to stir at room temperature for 7 hours, then poured into 5 mL of water and 5 mL of saturated ammonium chloride and extracted with 5 mL of ethyl acetate. The organic layer was separated and concentrated under vacuum, and the resulting residue was purified by silica gel column chromatography eluting with a gradient of 10 to 100% ethyl acetate in hexanes. Appropriate fractions were combined and concentrated under vacuum to give the desired compound (9, 243 mg). MS (ESI)[(M-18)+H+]+=365.1.

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, 5H-Pyrrolo[2,3-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ibrahim, Prabha N.; Spevak, Wayne; Cho, Hanna; US2009/306087; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-25-1, 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of methyl 5-chloropyrazine-2-carboxylate (8.00 g, 46.40 mmol) in THF (100 mL) was added NaBH4 (3.51 g, 93.00 mmol) under nitrogen atmosphere and the reaction mixture was stirred at 0 C for 5 h. The reaction was quenched with water (200 mL) and extracted with ethyl acetate ( 3 x 200 mL). The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Redisep-40 g, 30-40% EtOAc/n-hexane) to obtain Intermediate 112A (2.00 g, 29.80%) as a yellow solid.1H NMR (300 MHz, DMSO-d6) delta ppm 4.64 (d, J = 5.67 Hz, 2 H), 5.68 (t, J = 5.85 Hz, 1 H), 8.53 (s, 1 H), 8.72 (d, J = 1.13 Hz, 1 H). LCMS (Method-H ): retention time 0.476 min, [M+H] 145.2.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem