Tag: M.W=100-200

Synthetic Route of 16298-03-6,Some common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, molecular formula is C6H7N3O2, 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 1 : 5-Amino-6-(6-methyl-lH-benzimidazol-2-yl)-N-(tetrahydrofuran-2- ylmethyl)pyrazine-2-carboxamide (Compound 11-52)SCHEME IMETHOD A:Step 1: Methyl 3-amino-6-bromopyrazine-2-carboxylate[00139] A mixture of methyl 3-aminopyrazine-2-carboxylate (8.35 g, 54.53 mmol) and N- bromo-succinimide (9.705 g, 54.53 mmol) was stirred in MeCN (100 mL) at ambient temperature overnight. The resultant precipitate was filtered, washed with MeCN and dried to give the desired product as a yellow solid (1 1.68 g, 92percent Yield)XH NMR (400.0 MHz, DMSO) delta 3.85 (s, 3H), 7.55 (br s, 2H) and 8.42 (s, 1H) ppm; MS (ES+) 233.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-aminopyrazine-3-carboxylate, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); A1;,
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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. 6294-70-8, name is 5,6-Dimethylpyrazin-2-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 6294-70-8

At room temperature,Potassium tert-butoxide (5.60 g, 50 mmol)To a solution of 5,6-dimethylpyrazin-2-amine (1.23 g, 10 mmol)In 250 ml of dry THF.After stirring for 15 minutes,2-Nitrothiazole-4-carbonyl chloride (2.10 g, 11 mmol)In 50 ml of dry THF.The reaction mixture was stirred for 4 hours at room temperature,Then poured into saturated aqueous NaHCO 3 solution and extracted with EtOAc.The organic phase was washed with saturated aqueous NaCl solution,Dry over anhydrous Na2SO4 and concentrate to dryness.After purification by silica gel flash chromatography (cyclohexane / EtOAc: 90/10 to 50/50)Obtained as a white solid1.69 g of N- (5,6-dimethylpyrazin-2-yl) -2-nitrothiazole-4-amide(Yield: 61.0%).

The synthetic route of 6294-70-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mudanjiang Medical School; Liu Shijuan; Hou Jiafu; Li Xuemei; Zhou Xue; Wu Yiyan; Zhao Cong; Tong Lei; Zhang Chaoli; Liu Jiawei; Cui Xinyu; (11 pag.)CN107056819; (2017); A;,
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Pyrazine | C4H4N2 – PubChem

Related Products of 1320266-90-7,Some common heterocyclic compound, 1320266-90-7, name is 8-Chloro-3-isopropylimidazo[1,5-a]pyrazine, molecular formula is C9H10ClN3, 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.

To a stirred solution of 8-chloro-3-isopropylimidazo[i,5-ajpyrazine (31 g, 158.5 mmol) indry THF (300 mL) at -78 C under nitrogen was added n-butyllithium (2.5 M in hexanes,82.4 mL, 206 mmol), keeping the internal temperature below -65 C. After stirring for 30 mma solution of iodine (56.3 g, 221.8 mmol) in THF (50 mL) was added dropwise over 10 mmkeeping the internal temperature below -65 C during addition. The resulting suspension wasstirred for 1 hour whilst warming to -10 C then the reaction mixture was quenched by theaddition of saturated aqueous NH4C1 and extracted with 2-methyltetrahydrofuran (x3). The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by passage through a silica-gel pad, eluting with 0-20% EtOAc in DCM to give an orange solid, which was triturated with Et20 to givethe title compound 5B as a yellow solid (41.2 g, 81%). LC-MS: Rt = 1.29 mm, m/z = 322.0[M+Hj +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Chloro-3-isopropylimidazo[1,5-a]pyrazine, its application will become more common.

Reference:
Patent; OPTIKIRA LLC; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; KEENAN, Richard M.; BACKES, Bradley J.; MALY, Dustin J.; REYNOLDS, Charles; WHITTAKER, Ben; KNIGHT, Jamie; SUTTON, Jon; HYND, George; PAPA, Feroz, R.; OAKES, Scott, A.; (147 pag.)WO2019/46711; (2019); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 914452-71-4, 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 914452-71-4 as follows.

To a solution of 2-chloro-4-phenoxypyrrolo[2,1-J][1,2,4]triazine (100 mg, 0.407 mmol), 2-bromo-6-methylpyrazine (70.4 mg, 0.407 mmol) and hexamethylditin (0.084mL, 0.407 mmol) in 1,4-dioxane (7 mL) was added tetrakis(triphenylphosphine)palladium(0) (47.0 mg, 0.041 mmol). The reaction mixture was degassed with argon and was stirred at 100 C for 18 h. The solvent was removed under reduced pressure to get a brown solid. The crude residue was purified by silica gel chromatography (ethyl acetate:Petroleum ether, 10/90) to obtain 2-(6-methylpyrazin-2-yl)-4-phenoxypyrrolo[2,1-J][1,2,4]triazine (85 mg, 0.280 mmol, 68.8 % yield). LCMS m/z 304.4 (M+H); rt 1.45 mm; Conditions B.

According to the analysis of related databases, 914452-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; RAHAMAN, Hasibur; WARRIER, Jayakumar Sankara; SESHADRI, Balaji; (411 pag.)WO2017/15425; (2017); 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. 54013-07-9, name is 5-Methoxypyrazin-2-amine, A new synthetic method of this compound is introduced below., name: 5-Methoxypyrazin-2-amine

2-Amino-5-methoxypyrazine (1.5 g, 12.0 mmol; CASNo. 54013-07-9) was dissolved in anhydrous THF under nitrogen and cooled in a dry ice-acetone bath. To this solution was added pyridine (2.3 mL, 28.8 mmol). After 30 min phenyl chloroformate ( 1.7 mL, 13.2 mmol) was added dropwise. The reaction mixture was allowed to gradually warm to room temperature. After 2 hours ethyl acetate (90 mL) and water (45 mL) were added. The aqueous layer was back extracted once with ethyl acetate. The combined organic layers were washed twice with brine, then dried (MgSO4), filtered and concentrated. The residue was triturated with ether: ethyl acetate (50 mL: 2 mL). The solid was collected by vacuum filtration and washed with ether. To give the title compound as a pale yellow solid (2.5 g, 10.1 mmol, 85%) 1H NMR (400 MHz, DMSO-d6) delta ppm 10.79 (s, 1 H), 8.58 (s, 1 H), 8.13 (s, 1 H), 7.36-7.52 (m, 2H), 7.16-7.34 (m, 3H), 3.88 (s, 3H). m/z 246.1

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; PFIZER INC.; WO2009/127948; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 19847-12-2, These common heterocyclic compound, 19847-12-2, name is Pyrazinecarbonitrile, 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 synthesis of 2-aminomethylpyrazine (2-AMPZ) was synthesized according to the method described below with reference to the method described in the literature (Japanese Patent Laid-Open No. 2001-894594). 2-cyanopyrazine is 1.05 g (10 mmol) of 2-cyanopyrazine using Aldrich reagent and 100 mg of 60 wt% Ni / SiO2 was charged into a SUS316 autoclave together with 20 mL of toluene and purged with argon gas.This was pressurized to 50 atm with hydrogen gas and stirred at 140 C. for 4 hours.The reaction solution was filtered and concentrated to quantitatively obtain 2-aminomethylpyrazine (2-AMPZ).

The synthetic route of 19847-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kanto Chemical Co., Inc.; Hokkaido University; Katayama, Takeaki; Tsutsumi, Kunihiko; Murata, Kunihiko; Ohkuma, Takeshi; Arai, Noriyoshi; (35 pag.)JP2019/11367; (2019); A;,
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Electric Literature of 36070-80-1,Some common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

To a solution of 5-chloropyrazine-2-carboxylic acid (3 g, 18.9 mmol) in dichloromethane (60 mL) was added oxalyl dichloride (2.52 g, 1.7 mL, 19.9 mmol) dropwise at 0C. Then to the mixture was added 2 drops of DMF and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was concentrated in vacuo to give 5- chloropyrazine-2-carbonyl chloride (3.4 g, 100%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloropyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; SHEN, Hong; TAN, Xuefei; WU, Jun; CHEN, Dongdong; LI, Chao; WANG, Li; (156 pag.)WO2020/53249; (2020); A1;,
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Pyrazine | C4H4N2 – PubChem

1111638-10-8, name is 3-Chloro-5H-pyrrolo[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. Quality Control of 3-Chloro-5H-pyrrolo[2,3-b]pyrazine

A solution of 3-chloro-5H-pyrrolo[2,3-b]pyrazine (20 g, 131 mmol) and DIPEA (37 mL, 212 mmol) in NMP (100 mL) was stirred with cooling provided by a salt/ice-bath. 2-(Trimethylsilyl)ethoxymethyl chloride (28.3 mL, 160 mmol) in NMP (40 mL) was added over a period of 5-10 mm. The cooling bathwas removed, and the mixture stirred overnight at RT. A 5% aq. LiCI solution (100 mL) was added. EtOAc (400 mL) was added and the mixture transferred to a 2 L separating funnel. The aqueous layer was removed and the EtOAc layer was washed with further 5% aq. LiCI solution (3 x 100 mL). The EtOAc layer was then washed successively with 0.5 M aq. KHSO4 (2 x 100 mL), sat. aq. Na2CO3 (50 mL), 5% aq. LiCI (50 mL) and sat. brine solution (100 mL). The EtOAc layer was dried (MgSO4), filteredand evaporated, to give a dark oil. The residue was purified by column chromatography on silica gel (gradient elution, 0-50%, EtOAc/petrol), to give the title compound (31.8 g), MS: [M+H] = 284.

The synthetic route of 1111638-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; TAIHO PHARMACEUTICAL CO., LTD.; JOHNSON, Christopher Norbert; BUCK, Ildiko Maria; CHESSARI, Gianni; DAY, James Edward Harvey; FUJIWARA, Hideto; HAMLETT, Christopher Charles Frederick; HISCOCK, Steven Douglas; HOLVEY, Rhian Sara; HOWARD, Steven; LIEBESCHUETZ, John Walter; PALMER, Nicholas John; ST DENIS, Jeffrey David; TWIGG, David Geoffrey; WOODHEAD, Andrew James; (377 pag.)WO2019/167000; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 41110-28-5,Some common heterocyclic compound, 41110-28-5, name is 3-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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 solution of 3-methylpyrazinecarboxylic acid (Vishweshar, J. Org. Chem. 2002, 67, 556) (3.2 mL, 30 mmol) in ethanol (20 mL) was saturated with hydrogen chloride and stirred at 70 C. for 16 hours. The solution was concentrated, the residue was taken up in chloroform and the solution was washed with 1 N sodium hydroxide and brine, dried over magnesium sulfate and concentrated to dryness, leaving a brown solid (828 mg, 66%)

The synthetic route of 41110-28-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2005/234065; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, 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. Recommanded Product: 13924-95-3

Fluoromethyl toluene-4-sulfonate (Journal of Labelled Compounds & Radiopharmaceuticals, 46 (6), 555-566; 2003) (344 mg) and cesium carbonate (824 mg) were added to a solution of methyl 5-hydroxypyrazine-2-carboxylate (130 mg) in N,N-dimethylformamide (2.0 mL). The reaction solution was stirred at 70 C. for five hours and 30 minutes and then cooled to room temperature. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (18.0 mg).1H-NMR (400 MHz, CDCl3) delta (ppm): 4.03 (s, 3H), 6.14 (d, J=51.2 Hz, 2H), 8.42 (d, J=1.2 Hz, 1H), 8.94 (d, J=1.2 Hz, 1H).

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

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; US2010/93999; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem