Tag: M.W=200-300

Electric Literature of 87486-34-8, A common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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.

Example 17 A solution of the aminopyrazole (0.28 g, 2.5 mmol) and the dibromopyrazinone (0.74 g, 1.1 equiv) were heated to 120° C. in isopropanol for 1 h. The reaction mixture was cooled to RT, and the product was isolated by filtration (0.43 g, 57percent).

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2010/4231; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1379338-74-5, These common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]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.

Intermediate 18: 1,1-Dimethylethyl (3S)-3-{r(7-chloropyridor3,4-6lpyrazin-5- yl)oxy1methyl)-1-piperidinecarboxylate; 1 , 1-Dimethylethyl (3S)-3-(hydroxymethyl)-1-piperidinecarboxylate (129mg, 0.600mmol) (Apollo Scientific Limited) was taken up in N,N-dimethylformamide (DMF) (3ml), treated with sodium hydride (23.99mg, 0.600mmol) and allowed to stir at room temperature for 20min, a yellow solution resulted. 5,7-dichloropyrido[3,4- £>]pyrazine (100mg, 0.500mmol) was added and the reaction was allowed to stir at room temperature for a further 1 h. The reaction was partitioned between EtOAc (50ml) and NH4CI (50ml). The organic layer was dried using a hydrophobic frit and concentrated to give a brown oil. This oil was purified on silica (25g) using a 0-40% EtOAc/cyclohexane gradient. The appropriate fractions were summed and concentrated to give the title compound as a yellow gum (91 mg).LCMS (Method B): Rt = 1.26min, MH+ = 378.88

Statistics shows that 5,7-Dichloropyrido[3,4-b]pyrazine is playing an increasingly important role. we look forward to future research findings about 1379338-74-5.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (2012); A1;,
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Pyrazine | C4H4N2 – PubChem

Application of 369638-68-6,Some common heterocyclic compound, 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, molecular formula is C10H15N3O2, 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. 5-methylpyrazin-2-amine; To a solution tert-butyl 5-methylpyrazin-2-ylcarbamate (1.5 g, 7.17 mmol) in CH2CI2 (20 ml) was added TFA (2.6 mL, 35.86 mmol). The reaction mixture was stirred for 4 hours at room temperature after which, it was concentrated under reduced pressure. The reaction mixture was diluted with CH2CI2 and neutralized with sai.NaHCOs solution. The organic layer was separated and the aqueous layer was extracted with CH2CI2. The combined organic extracts were washed with brine, dried over MgS04, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (30% to 50% Ethyl acetate/Hexane) as a solvent to afford title compound (580 mg, 74% yield). MS m/z : 110 [M+l] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (5-methylpyrazin-2-yl)carbamate, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; WO2011/90738; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 24241-18-7, The chemical industry reduces the impact on the environment during synthesis 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, I believe this compound will play a more active role in future production and life.

(a) Add 2-amino-3,5-dibromopyrazine (10 g, 39.54 mmol, 1 eq) to a 100 mL autoclaveAnd ammonia (50 mL, commercially available),Raise the temperature to 130 C under nitrogen protection conditions and carry out the reaction overnight (10 to 12 hours);Cooling, suction filtration,The obtained solid was vacuum dried to give 5.0 g of Compound II.

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, 2-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Suzhou Derivative Biological Technology Co., Ltd.; Liu Ke; (6 pag.)CN108395436; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1379338-74-5, A common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, molecular formula is C7H3Cl2N3, 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.

The mixture of (9H-fluoren-9-yl)methyl hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate (100 mg, 0.5 mmol) and 5,7-dichloropyrido[4,3-b]pyrazine (600 mg, 1.8 mmol) in dioxane was stirred at 0 C. for 30 minutes and then at room temperature for 4 hours. The mixture was concentrated, and the residue was purified by chromatography to give the title compound. MS (m/z): 498 (M+H)+.

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; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 3,6-dibromopyrazine-2-carboxylate

To a solution of methyl 2,5-dibromo pyrazine carboxylate (40g, 135mmol) in toluene (300ml) were dropwise added K2CO3 (28g, 202mmol) and N-ethyl-N- cyclohexylamine (35g, 270mmol). The reaction mixture was refluxed at 120C for 3 with stirring, and then cooled to room temperature. After extraction with ethyl acetate, the organic layer thus formed was washed with 2N HCI and further with water. Then, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to afford the title compound (46g, 99%). 1H NMR (400MHz, CDCI3) 8.15 (s, 1 H), 3.92 (s, 3H), 3.50 (, 3H), 1.81 (m, 4H), 1.66 (m, 2H), 1.57 (m, 2H), 1.28 (m 2H), 1.12 (t, 3H).

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; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 221136-66-9, 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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

Example 8 r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acid ethyl ester(3-Bromo-6-methyl-2-oxo-2H-pyrazin-1 -yl)-acetic acid ethyl ester was reacted with 2,2-difluoro-2-phenyl-ethylamine in the presence of a base, at elevated temperature, to yield the title compound as shown in the Scheme above. Table 5 below lists the reagent amounts, base and temperature combinations applied to this reaction, as well as yield.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6966-01-4, name is Methyl 3-amino-6-bromopyrazine-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. Safety of Methyl 3-amino-6-bromopyrazine-2-carboxylate

Step 1 : 3-amino-6-bromo-N-methylpyrazine-2-carboxamide[00261] Methyl 3-amino-6-bromo-pyrazine-2-carboxylate (7.5 g, 32.32 mmol) was suspended in 40% aqueous methylamine and the resulting mixture stirred vigorously at RT for 4 hours. The resultant precipitate was collected, washed with water and dried to give the desired product(6.73g, 90% Yield). IH NMR (400.0MHz, DMSO) d 2.76 (s, 3H), 7.75 (br s, 2H), 8.34 (s, IH),8.58 (b rs, IH) ppm; MS (ES+) 232.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1196152-38-1, A common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, molecular formula is C5H2BrF3N2, 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.

Example 81N- (3,4-Dif [uoropheny[)-3-methy[-5-{[5- (trif[uoromethy[)pyrazin-2-y[]amino- 1 ,2-thiazo[e-4-carboxamide A mixture of 5-amino-N-(3,4-dif[uoropheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide [Intermediate 3] (100 mg, 0.37 mmo[, 1.0 eq), 2-bromo-5-(trif[uoromethy[)- pyrazine [CAS-RN: 1196152-38-1] (105 mg, 0.45 mmo[, 1.2 eq) and cesiumcarbonate (242 mg, 0.74 mmo[, 2.0 eq) in 4.0 mL dioxane/DMF (7/1) was p[aced ina microwave via[ that was f[ushed with argon. Then, pa[[adium(II) acetate (8 mg,0.04 mmo[, 0.1 eq) and Xantphos (21 mg, 0.04 mmo[, 0.1 eq) were added.Afterwards, the via[ was sea[ed and the reaction mixture was stirred at anenvironmenta[ temperature of 110 C for 4 h. On coo[ing, the reaction mixture was partitioned between ethy[ acetate and water. The organic phase was washed with brine and the phases were separated by the use of a Whatman fi[ter. The vo[ati[e components of the organic phase were removed in vacuo. Purification was conducted via preparative HPLC (Method A) to give 36 mg (22 % yie[d of theory) ofthe tit[e compound.UPLC-MS (Method 1): Rt = 1.36 mm; MS (ESIneg) m/z = 414 [M-H].1HNMR (400 MHz, DMSO-d6): oe [ppm] = 2.46 (s, 3H), 7.34-7.54 (m, 2H), 7.95 (dd, 1H), 8.82 (s, 1H), 8.91 (s, 1H), 10.53 (s, 1H), 11.46 (s, 1H).

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3, A common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, molecular formula is C4H3BrClN3, 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.

3-Bromo-5-chloropyrazin-2-amine (200 mg, 0.96 mmol),Triethylamine (290 mg, 2.88 mmol), cuprous iodide(5mg, 0.33mmol)And bis(triphenylphosphine)palladium dichloride (13 mg, 0.02 mmol) was dissolved in tetrahydrofuran (5 mL).The reaction solution was stirred at room temperature.Then trimethylethynyl silicon (0.15 mL, 1.06 mmol)Slowly adding dropwise to the above reaction solution,After completion of the dropwise addition, the resulting reaction solution was heated to 55 C to continue the reaction for 1 hour.After the reaction system is cooled to room temperature,The reaction solution was diluted with ethyl acetate (50 mL).Filter and concentrate the filtrate under reduced pressure.The residue obtained was purified by silica gel column chromatography (PE/EA (v/v) = 30/1).The title compound was obtained as a pale yellow solid ( 208 g, 96%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; Nie Biao; Xu Juan; Yan Huan; Chen Jianping; (90 pag.)CN108727369; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem