Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 1111638-10-8, name is 3-Chloro-5H-pyrrolo[2,3-b]pyrazine, 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 1111638-10-8, Recommanded Product: 3-Chloro-5H-pyrrolo[2,3-b]pyrazine

Step 4; A suspension of NaH (370 mg, 15.62 mmol) in DMF (15 mL) was cooled to 0 C. and treated with 4 (1.6 g, 10.41 mmol) dissolved in DMF (15 mL). The reaction mixture was stirred 20 min at 25 C. The reaction mixture was again cooled to 0 C., SEM-Cl (2.2 mL, 12.50 mmol) was added slowly, and allowed to stir at 25 C. for 2 h. TLC (20% EA/Hexane) indicates complete consumption of starting material. The solvent was distilled off and the residue was purified by column chromatography over silica gel (100-200 mesh) eluting with EtOAc/Hexane (5-10%) to provide 5 as a brown oily liquid (2.0 g, 67%). MS m/z (ES): 284 (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, 3-Chloro-5H-pyrrolo[2,3-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; de Vicente Fidalgo, Javier; Hermann, Johannes Cornelius; Lemoine, Remy; Li, Hongju; Lovey, Allen John; Sjogren, Eric Brian; Soth, Michael; US2011/59118; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, 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 486460-21-3, Safety of 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

Diisopropylethylamine at 0 C(Trifluorobenzyl) -5,6,7,8-tetrahydro- [1, 3-methyl-5-oxazol- 2,4] triazolo [4,3-a] pyrazine hydrochloride (3.37 g, 14.8 mmol) in dichloromethane (80 mL).A solution of 1-hydroxybenzotriazole (2.40 g, 17.8 mmo 1)After stirring, continue stirring at 0 C for 10 minutes,Then 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (3.40 g, 17.8 mmol) was added portionwise.Stir overnight at room temperature.After the reaction,Washed with saturated aqueous sodium bicarbonate solution,Drying and passing through column chromatography (RhoEpsilon: EpsilonAlpha = 1: 1 to 100 Epsilon) gave a white solid 9 (7.2 g, 95.2% yield)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Biortus Biosciences Co.,Ltd; ZHANG, HAI JUN; ZHANG, SHUAI; BIAN, WANG DONG; (12 pag.)CN103483340; (2016); B;,
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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromopyrazine

Crystals of 2 were obtained by the slow-diffusion method between 3 layers: 1st layer is a solution of Fe(OTs)2*6H2O(0.096 g, 0.2 mmol, 1 equiv.) and NH4SCN (0.030 g, 0.4 mmol, 1 equiv.) in a water/methanol mixture (1/1, 10 ml); 2nd one is a water/methanol mixture (1/1, 10 ml); 3rd one is a solution of 2-bromopyrazine (0.127 g, 0.8 mmol, 1 equiv.) in methanol (3 ml). After 2 weeks red plates grew in the second layer; they were collected, washed with water and dried in air. Yield is 0.050 g (50%). Anal. Calc. for Fe1C18H16O2N10S2Br4: C, 25.59; H, 1.90; N, 16.58; S,7.58. Found: C, 24.91; H, 1.77; N, 16.42; S, 7.67%. Principal IR absorption bands for 2 (cm-1): 2080 (s), 1510 (m), 1456 (m),1381 (s), 1130 (s), 1057 (m), 1056 (m), 1020 (s).

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shylin; Gural Skiy; Bykov; Demeshko; Dechert; Meyer; Hauka; Fritsky; Polyhedron; vol. 87; (2015); p. 147 – 155;,
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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine

Example 32 (5,6-Dihydro-8H-imidazo[1,2-a]pyrazin-7-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone A mixture of sodium 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylate (0.3 g) and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine (0.24 g). HBTu (0.4 g), DIEA (1 mL), THF (3 mL) and DMA (3 mL) was stirred at room temperature for three hours. The reaction mixture was then partitioned between EtOAc and water, the organic layer washed with saturated NaHCO3 and water, dried over Na2SO4 and concentrated in vacuo. The residue was purified via prep. TLC (10% MeOH/DCM) to give 56 mg of (5,6-dihydro-8H-imidazo[1,2-a]pyrazin-7-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone. MS (M+H)=578.

According to the analysis of related databases, 91476-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gong, Leyi; Tan, Yun-Chou; US2011/301170; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 13515-06-5,Some common heterocyclic compound, 13515-06-5, name is 5,6-Dimethylpyrazine-2-carboxylic acid, molecular formula is C7H8N2O2, 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.

5,6-dimethylpyrazine acid (248 mg, about 2 mmol, prepared as Example 2), 4-chloro-1-butanol (2.4mmol), EDCI (2.4mmol) and DMAP (0.2mmol) were added to dry methylene chloride (20mL), stir at room temperature for 12 hours, then dilute with dichloromethane (20mL), The saturated aqueous NaCl solution was washed, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain an oily liquid. The hederagenin(236mg, 0.5mmol), K2CO3 (207mg, 1.5mmol) and oily liquid were added to DMF (20mL), The mixture was stirred at 85 C for 4 hours. It was then diluted with ethyl acetate (20 mL), washed with saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to obtain a white powder, H-17. Yield: 27% (after chromatograph with DCM / MeOH, 1% -2%) as a white powder, m.p .: 134.7 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dimethylpyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; Xinhuo Zhiyao (Beijing) Technology Co., Ltd.; Fang Kang; Guo Wenbo; Wang Penglong; Cheng Gang; (26 pag.)CN110964078; (2020); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-25-1, 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. 33332-25-1 name is Methyl 5-chloropyrazine-2-carboxylate, 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.

Combine 5-CHLOROPYRAZINE-2-CARBOXYLIC acid methyl ester (626 mg, 3.64 mmol), phenylboronic acid (666 mg, 5.45 mmol), cesium fluoride (55 mg, 0.36 mmol) and NA2CO3 (964 mg, 9.09 mmol) in DMF (5 mL) and water (5 mL) with stirring. Place the hetereogeneous reaction mixture, open to the air, in an oil bath maintained at 80C. After 5 minutes of heating, add Pd (OAC) 2 (81 mg 0.36 mmol) in one portion and stir until reaction turns black. Cool the reaction to room temperature, dilute with ethyl acetate, and filter through a short plug of celite with additional ethyl acetate. Wash the organics with water, dry over MGS04, filter and evaporate. Purification by flash column chromatography yields 2-phenylpyrimidine-5-carboxylic acid methyl ester as a yellow solid. Dissolve the purified ester in THF (0.25M) and add an equal volume of 1M NAOH. Stir vigorously at room temperature for 15 hours. Upon completion, acidify the reaction with conc. HCI and extract with ethyl acetate. Evaporation of the solvent yields 63 mg (8%) of the title COMPOUND. H NMR (DMSO): 9.37 (s, 1H), 9.21 (s, 1H), 8.23-8. 21 (m, 2H), 7.57-7. 77 (m, 3H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/94382; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5424-01-1, 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. 5424-01-1, name is 3-Aminopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Compound 1 (5 g, leq) was added to methanol (50 ml)Ice water bath by adding concentrated sulfuric acid (4eq),The reaction was stirred at room temperature,TLC showed complete reaction,concentrate,Saturated sodium carbonate adjusted to pH = 8,Filter, 50 dry 2h,A brown solid 2 (4.18 g,76%).

The chemical industry reduces the impact on the environment during synthesis 3-Aminopyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Central South University; Liu Fengliang; Li Cuiqin; (19 pag.)CN106866553; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 91476-80-1, 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 150 mg (0.28 mmol) of 2-[(3R)-3-methylmorpholin-4-yl]-8-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]-1,7-naphthyridin-4-yl trifluoromethanesulfonate and 119 mg (0.97 mmol) 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine in 0.42 ml of MeCN was stirred at 70C for 48 h under argon. After cooling the reaction mixture was diluted with ethyl acetate and THE and washed with saturated aqueous sodium chloride solution. The organic phase was filtered using a Whatmanfilter and then concentrated to give the crude product that was used without further purification in the next step.

The chemical industry reduces the impact on the environment during synthesis 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WORTMANN, Lars; LUeCKING, Ulrich; LEFRANC, Julien; BRIEM, Hans; KOPPITZ, Marcus; EIS, Knut; VON NUSSBAUM, Franz; BADER, Benjamin; WENGNER, Antje Margret; SIEMEISTER, Gerhard; BONE, Wilhelm; LIENAU, Philip; GRUDZINSKA-GOEBEL, Joanna; MOOSMAYER, Dieter; EBERSPAeCHER, Uwe; SCHICK, Hans; (509 pag.)WO2016/20320; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-28-4, name is 2-Amino-6-chloropyrazine, 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 2-Amino-6-chloropyrazine

4. 2-Chloro-3-bromo-6-aminopyrazine and 2-amino-3-bromo-6-chloropyrazine A solution of 2-chloro-6-aminopyrazine (20 g, 0.15 mole) in chloroform (1940 ml) was stirred at -5¡ã C. to 0¡ã C. N-Bromosuccinimide (27.58 g, 0.15 mole) was added in portions maintaining the temperature between -5 and 0¡ã C. The mixture was warmed to room temperature and stirred for 3.50 hrs. The mixture was then washed with aqueous saturated sodium bicarbonate (1*300 ml), then water (1*500 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated down in vacuo. The residue was purified by ‘flash chromatography’ using chloroform as the eluent. Yield of 2-chloro-3-bromo-6-aminopyrazine 13.89 g (43percent), M.p. 146-147¡ã C. Yield of 2-amino-3-bromo-6-chloropyrazine 4.90 g (15percent), M.p. 124-125¡ã C.

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Wellcome, Inc.; US6255307; (2001); B1;,
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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of (3-Chloropyrazin-2-yl)methanamine hydrochloride

To a solution of 3-isopropyl-3- (methoxycarbonyl) cyclohexanecarboxylic acid (4.4 g, 19.3 mmol) in THF (100 mL) was added (3-chloropyrazin-2-yl) methanamine hydrochloride (5.2 g, 28.9 mmol) , HATU (11 g, 28.9 mmol) and TEA (11.7 g, 115.8 mmol) . The mixture was stirred at room temperature overnight. The reaction mixture was diluted with EA and water, the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with PE/THF 5/1 to give methyl 3- ( ( (3-chloropyrazin-2-yl) methyl) carbamoyl) -1-isopropylcyclohexanecarboxylate. 1H NMR (400 MHz, CDCl3) delta ppm: 0.86 (t, J 6.65 Hz, 6 H) , 1.16 -1.32 (m, 2 H) , 1.36 -1.47 (m, 2 H) , 1.69 -1.87 (m, 3 H) , 2.07 -2.16 (m, 1 H) , 2.22 -2.42 (m, 2 H) , 3.69 (s, 3 H) , 4.56 -4.76 (m, 2 H) , 6.79 (s, 1 H) , 8.31 (d, J 2.74 Hz, 1 H) , 8.45 (d, J 2.74 Hz, 1 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; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ANDRESEN, Brain M.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (111 pag.)WO2016/106624; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem