Tag: M.W=200-300

The chemical industry reduces the impact on the environment during synthesis 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life. 486424-37-7

(Step 2) (1084) To a solution of 3-amino-6-bromopyrazine-2-carboxylic acid (10 g, 45.87 mmol) in DMF (50 mL) were added HATU (26.16 g, 68.8 mmol) and DIEA (80.1 mL, 458.7 mmol) at room temperature. Ethylamine (2 mol/L, THF solution, 114.65 mL, 229.3 mmol) was added thereto at room temperature, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, to the residue was added ethyl acetate, and the solution was washed with water. The aqueous layer was extracted with ethyl acetate (x3). The organic layer was washed with water and saturated brine, and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; 15% ethyl acetate/hexane) to give 3-amino-6-bromopyrazine-2-carboxylic acid ethylamide (6.60 g, 59%) as a pale yellow solid. 1H-NMR(400MHz,DMSO-d6) :delta1.10(t,3H,J=7.20Hz),3.24-3.30(m,2H),7.69(brs,2H),8.33(s,1H),8.60(t-like,1H,J=5.44Hz).

The chemical industry reduces the impact on the environment during synthesis 486424-37-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; SATO, Ayumu; KOUNO, Mitsunori; TOMATA, Yoshihide; OCHIDA, Atsuko; YONEMORI, Kazuko; ODA, Tsuneo; IMADA, Takashi; YUKAWA, Tomoya; (238 pag.)EP2975031; (2016); 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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., 1458-18-0

Under an argon atmosphere,Isoamyl nitrite (26.6 mL, 200 mmol) was added to a THF solution of methyl 3-amino-5,6-dichloropyrazine-2-carboxylate (4.44 g, 20.0 mmol) in THF (30 mL). The reaction mixture was stirred at 80 C. for 17 hours. After standing to cool, the low boiling point compound was distilled off to obtain a crude product. This crude product was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 100/0 to 90/10) to obtain methyl 5,6-dichloropyrazine-2-carboxylate (2.29 g, 55% ) As a white solid.

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; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE; AIHARA, HIDENORI; SHONO, TOMOHIRO; (23 pag.)JP2015/140319; (2015); A;,
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

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

Some common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, molecular formula is C4H3Br2N3, 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. 24241-18-7

A 500ml three-neck flask, was added morpholine (9.6g, 0.11mol) and 2-amino-3,5-dibromo-pyrazine (25.3g, 0.1mol) and N- methylpyrrolidinone (100ml), and at 80 reaction 6h, TLC tracking, cooled to room temperature, add water 400ml, stirring, suction filtered and dried to give a yellow solid 22.5g, a yield of 86.7%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24241-18-7, its application will become more common.

Reference:
Patent; Hubei University of Technology; Liu, Mingxing; Jiang, Weidong; Wang, Wanxia; (6 pag.)CN105622526; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, molecular formula is C16H11ClN2, 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. 41270-66-0

Under the protection of nitrogen,Add 3-methyl-2-chloro-quinoxaline (532 mg, 2.00 mmol) to cis-5-(isopropylaminomethyl)tetrahydrofuran-2-yl)methanol (1.04 g, 6.00 mmol)N-methylpyrrolidone(50mL) solution,The reaction was heated to 190 C for 15 h, and the reaction was monitored by LC-MS.The reaction was cooled, and ice water was added to the mixture, and ethyl acetate (50mL*3)The organic mixed phase was washed with water (50 mL) and saturated brine (50 mL*2).Filtration, solvent removal under reduced pressure, purification by chromatography on silica gel column, and collected under reduced pressure.Drying in vacuo gave 641.5 mg of Compound VIII as a white solid.Yield: 79.6%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41270-66-0, its application will become more common.

Reference:
Patent; Chengdu Yuandong Bio-pharmaceutical Co., Ltd.; Zeng Yanqun; Yan Shengyong; Zhang Tao; Wang Ying; (17 pag.)CN108623541; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

24241-18-7, These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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.

To a solution of intermediate I-82 (10 g, 40 mmol, 1.0 eq) in DMF (115 mL) was added neat triethylamine (53 mL), Pd(PPh3)4 (2.3 g, 2.0 mmol, 0.05 eq) and CuI (0.90 g, 4.7 mmol, 0.12 eq) followed by drop wise addition of ethynyltrimethylsilane (6.7 mL, 48 mmol, 1.2 eq) and the reaction mixture was stirred for 30 minutes at 120 C. The crude reaction mixture was concentrated by evaporation and the crude reaction product was purified by silica gel column chromatography to give intermediate I-83 (3.0 g, 17%) as yellow oil. MS (ESI): m/z 271 (M+H+).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 24241-18-7.

Reference:
Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

41270-66-0, Name is 5-Chloro-2,3-diphenylpyrazine, 41270-66-0, 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.

2-[4-(tert-butoxycarbonyl)(isopropyl)aminobutoxy]-N-(methylsulfonyl)acetamide (20.0 g, 0.055 mol)And dissolved in methanol (110 mL),Trifluoroacetic acid (6.8 g, 0.06 mol) was added and the reaction stirred at 65 C for 6 hours until the reaction was complete. The reaction mixture was added dropwise to stirred water (200 mL), cooled to 0 C for 3 hours and filtered to give the intermediate compound 2- [4- (isopropyl) aminobutoxy] -N- (methylsulfonyl) acetamide) and then dissolved in methanol (40 mL)5-Chloro-2,3-diphenylpyrazine (16.0 g, 0.06 mol)N, N-diisopropylethylamine (15.5 g, 0.12 mol),The reaction mixture was stirred for 8 hours at 100 C. The reaction mixture was allowed to cool to room temperature. Water (40 mL) was added and the mixture was cooled to -10 C for 3 hours. The resulting mixture was filtered to give a solution of celecoxib (25.0 g) , The reaction of this step is as follows

Statistics shows that 5-Chloro-2,3-diphenylpyrazine is playing an increasingly important role. we look forward to future research findings about 41270-66-0.

Reference:
Patent; Hunan Ouya Biological Co., Ltd.; Li Xingmin; (10 pag.)CN105949135; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5900-13-0, 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 5900-13-0 as follows.

5-bromo-3-methoxy-2-pyrazinamme (13.5g), hexane-2,5-dione (9g) and para- toluenesulphonic acid hydrate (0.5g) in toluene (200ml) was heated under reflux using a Dean and Stark trap to collect the water. After 16h, the solution was allowed to cool, EPO concentrated to 50ml and passed through a pad of silica gel eluting with dichloromethane to collect the subtitle compound. Yield 17g.1H NMR (D6-DMSO):8.25 (IH, s), 5.92 (2H, s), 4.02 (3H, s), 2.02 (6H, s)

According to the analysis of related databases, 5-Bromo-3-methoxypyrazin-2-amine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/35154; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

32111-21-0, A common compound: 32111-21-0, name is 2-Iodopyrazine, 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.

Step C: A solution of 5-(4-chloro-phenyl)-l-(3-methanesulfonyl-phenyl)-6-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-l,5-dihydro-pyrazolo[3,4-d]- pyrimidin-4-one (8, 0.5 g, 0.829 mmol) in N,N-dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.26 g, 1.2 mmol), cesium carbonate (0.54 g, 1.7 mmol), Pd(dppf>2Cl2 (0.06 g, 0.08 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 100 0C for 3 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3 *). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by preparative HPLC to afford 5-(4-chloro-phenyl)-l-(3-methanesulfonyl-phenyl)-6-(4-pyrazin- 2-yl-phenyl)-l,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (9). 1H NMR (DMSO-d6, 400 MHz) delta 9.25 (s, IH), 8.71 (m, IH), 8.68 (m, IH), 8.63 (m, IH), 8.61 (m, IH), 8.55 (m, IH), 8.09 (m, 2H), 7.95 (m, IH), 7.88 (m, IH), 7.62 (m, 2H), 7.45 (m, 4H), 3.30 (s, 3H); LC-MS calculated for C28H19ClN6O3S (M+H*) 555.1, found 555.0.

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-Iodopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem