Tag: M.W=100-200

Synthetic Route of 5521-58-4, 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. 5521-58-4, name is 5-Methylpyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 4-[3-(5-Methyl-pyrazin-2-yl)-ureido]-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester. To a stirred, cooled (about 0 C.) solution of 4-amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester (258 mg, 1.0 mmol) in toluene (3.0 mL) was added triethylamine (139 muL, 1.0 mmol) and triphosgene (98 mg, 0.33 mmol). After stirring for 30 minutes, 5-methyl-2-amino pyrazine (109 mg, 1.0 mmol) was added and the reaction was heated to 65 degrees C. The reaction was allowed to cool to room temperature, then diluted with ethyl acetate (50 mL) and water (50 mL). A precipitate formed which was filtered and dried under reduced pressure to yield the desired material as a white solid (47% yield). 1H-NMR (400 MHz, d6-DMSO) delta10.29 (s, 1H), 8.79 (s, 1H), 8.68 (d, 1H, 8.59 (br s, 1H), 8.48 (d, 1H), 7.70 (s, 1H), 7.62 (d, 1H), 7.51 (m, 1H), 5.32 (s, 2H), 3.88 (s, 3H), 2.32 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 5-Methylpyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); 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. 5424-01-1, name is 3-Aminopyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 3-Aminopyrazine-2-carboxylic acid

15 g of 3-aminopyrazine-2-carboxylic acid was added to 200 ml of methanol.Add 10 ml of thionyl chloride, stir overnight at room temperature, and concentrate.200 ml of toluene was added and concentrated to give 18 g of 3-aminopyrazine-2-carboxylic acid methyl ester.

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; Changsha Shencheng Biological Technology Co., Ltd.; Bu Gonggaofamingren; (5 pag.)CN107513041; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 14399-37-2, 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. 14399-37-2, name is 3,6-Dichloropyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a 200 mL round bottom flask was added Na2S (10.816 g, 44wt% containing crystalline water, 60.978mmol) and toluene (100 mL). The mixture was heated to reflux, and water was removed with a Dean-Stark trap (about 5~6 mL water was distilled out). After cooling, the mixture was concentrated to dry.To above round bottom flask was added Y7d (5.000 g, 30.489mmol) and 2-methylbutan-2-ol (50 mL), the reaction was heated to reflux and stirred for 36 h. After cooling to 25 C, the mixture was filtered. The solvent of the filtrate was exchanged with n-heptane (5 V*3 times, based on Y7d), and finally concentrated to IV residue. THF (25 mL) was charged to the residue at 25 C and stirred. The suspension was filtered and washed with THF/n-heptane (5 mL/5 mL) to give a brown solid (6.200 g).To another 200 mL round bottom flask was added above brown solid (6.200 g),10% brine (25 mL), Me-THF (30 mL) and n-BmNBr (9.829 g, 30.489 mmol). The mixture was stirred for 0.5 h at room temperature, and the phases were separated. The organic phase was washed with 20% brine (25 mL), and exchanged the solvent with /.vo-propanol (5 V *3 times, based on Y7d) to give the /.vo-propanol solution of Y7c (27.000g, 99.2% purity by HPLC area, 58.08% assay yield). 1H NMR (400 MHz, DMSO-d6) d = 6.88 (s, 1H), 2.97 – 2.92 (m, 14H),1.38 – 1.31 (m, 14H), 1.13 – 1.04 (m, 14H), 0.73 – 0.69 (t, 21H). The advantage of the use of n- Bu4NBr (or other corresponding tert-alkylaminohalogenide) is easier workup and purification.

The synthetic route of 3,6-Dichloropyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; ZHANG, Hao; JIA, Huanqing; WANG, Hui; WANG, Jianhua; LI, Wei; LIN, Xiaohui; MIN, Zhongcheng; (91 pag.)WO2020/65452; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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: Methyl 5-chloropyrazine-2-carboxylate

Example 190C methyl 5-ethenylpyrazine-2-carboxylate (1430) A solution of methyl 5-chloropyrazine-2-carboxylate (3 g, 17.38 mmol), potassium vinyltrifluoroborate (5.12 g, 38.2 mmol) and 1,1?-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (1.272 g, 1.738 mmol) in isopropyl alcohol (45 mL, anhydrous) was treated with triethylamine (4.85 mL, 34.8 mmol) and the atmosphere was vacuum purged with N2 a few times. The mixture was heated at 80 C. under N2 for 2 hours and cooled. The mixture was partitoned between saturated aqueous NaHCO3 solution (50 mL) and ethyl acetate (150 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate layers were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with a gradient of 25 to 100% ethyl acetate in heptanes to provide the title compound (2.28 g, 13.89 mmol, 80% yield)1H NMR (400 MHz, CDCl3) delta 9.23 (d, J=1.0 Hz, 1H), 8.67 (d, J=1.1 Hz, 1H), 6.89 (dd, J=17.4, 10.8 Hz, 1H), 6.51 (d, J=17.4 Hz, 1H), 5.78 (d, J=10.9 Hz, 1H), 4.03 (s, 3H); LC/MS (ESI+) m/z 165 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33332-25-1, its application will become more common.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 75907-74-3,Some common heterocyclic compound, 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, molecular formula is C8H12N2O, 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 suspension of 3,5,6-trimethylpyrazine-2-yl)methanol (see Bioorg. Med. Chem. 2007, 15, 3315; 14.8 g, 97.2 mmol) and manganes(IV) oxide (30.0 g) in dichloromethane was stirred at room temperature for 3 days. The reaction mixture was filtrated through Celite with dichloromethane. The filtrate was combined and concentrated in vacuo to give 3,5,6-trimethylpyrazine-2-carbardehyde. MS (APCI): m/z 151 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3,5,6-Trimethylpyrazin-2-yl)methanol, its application will become more common.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; KAWANISHI, Eiji; HONGU, Mitsuya; TANAKA, Yoshihito; WO2011/105628; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H16N2O2

A 5 L- 3 necked round bottomed flask, equipped with a mechanical stirrer, temperature probe, addition funnel and N2 inlet, was charged with the Schollkopf chiral auxiliary-(Int-13a, 200 g, 1.09 mol, 1.0 eq), bis(chloromethyl) dimethylsilane (Int-13b, 256 g, 1.63 mol, 1.5 eq), and THF (2 L, Aldrich anhydrous). The flask was cooled in a dry ice/ 2-propanol bath until the internal temperature reached -75 °C. n-Butyllithium (Aldrich 2.5 M in hexanes , 478 mL, 1.19 mol, 1.09 eq) was added via a dropping funnel over 1 hour while maintaining the internal reaction temperature between -67 °C and – 76 °C. The resulting orange-red solution was allowed to gradually warm to room temperature for about 15 hours. The reaction mixture was then re-cooled to 0 °C and quenched with 500 mL of water. Diethyl ether (2L) was added and the layers were separated. The aqueous layer was extracted with 1 L of diethyl ether. The combined organic extracts was washed with water and brine, dried with MgSC^, filtered, and concentrated in vacuo, giving 480 g of orange oil. This material was left in vacuo for about 15 hours to provide 420 g of oil. The crude product was split into two batches and purified via silica gel chromatography on a 1.6 kg flash column. The column was eluted with gradient of 0-4percent Epsilon20 in hexanes. The product fractions were concentrated in vacuo at a bath temperature at or below 40 °C giving 190 grams of Int-13c-(60percentyield).

The synthetic route of 109838-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph A.; ROSENBLUM, Stuart B.; COBURN, Craig A.; SHANKAR, Bandarpalle, B.; ANILKUMAR, G., Nair; CHEN, Lei; DWYER, Michael, P.; JIANG, Yueheng; KEERTIKAR, Kartik, M.; LAVEY, Brian, J.; SELYUTIN, Oleg, B.; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; RIZVI, Razia; ZENG, Qingbei; WO2012/41014; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 21279-64-1, name is 5-Chloropyrazine-2-carboxamide, 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. Product Details of 21279-64-1

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 5-Chloropyrazine-2-carboxamide 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

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, 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 36070-75-4, COA of Formula: C5H2ClN3

To a microwave vial was added (2S,3R,4R)-ethyl 1-acetyl-4-amino-2,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (for a preparation see Intermediate 4, 200 mg, 0.689 mmol) and 5-chloropyrazine-2-carbonitrile (192 mg, 1.378 mmol). DMSO (1 mL) was added, followed by DIPEA (0.361 mL, 2.066 mmol) and the microwave vial sealed and heated to 160 C for 30 min in a microwave reactor. H20 (20 mL) was added, followed by Et20 (20 mL) and the layers separated. The aqueous layer was further extracted with Et20 (2 x 20 mL) and the combined organics then back extracted with brine (2 x 20 mL). The combined organics were then dried (Na2S04) and concentrated in vacuo to afford a brown oil. This was loaded in DCM and purified by column chromatography (25 g silica) using a gradient of 0-60% EtOAc / cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford the product as a brown oil (268 mg). LCMS (2 min Formic): Rt = 1.01 min, [MH]+ = 394.

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, 5-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen, John; HIRST, David, Jonathan; HUMPHREYS, Philip, G.; LINDON, Matthew, J.; PRESTON, Alexander, G.; SEAL, Jonathan, Thomas; WELLAWAY, Christopher, Roland; (66 pag.)WO2016/38120; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H7N3O2

Hydrazine monohydrate (34 mL, 1094.95 mmol) was added portionwise to a stirred suspension of methyl 3-aminopyrazine-2-carboxylate (21.3 g, 139.09 mmol) in ethanol (65 mL) at r.t. The resulting slurry was stirred at 60 °C for 2 hours, cooled to room temperature and filtered. The solid was washed with cold ethanol (2 x 25 ml) and dried to a constant weight to afford 3-aminopyrazine-2-carbohydrazide (20.75 g, 97 percent) as a beige solid: 1H NMR Spectrum: (DMSO-d6) 4.49 (2H, d), 7.46 (2H, br s,), 7.78 (IH, d), 8.17 (IH, d), 9.79 (IH, t); Mass Spectrum [M+H]+ = 154.

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard Christophe; BERRY, David; DELOUVRIE, Benedicte; HARRIS, Craig Steven; LAMBERT-VAN DER BREMPT, Christine Marie Paul; OUVRY, Gilles; REID, Gary Patrick; TOMKINSON, Gary Peter; WO2014/114928; (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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., Quality Control of 2-Amino-6-chloropyrazine

2,2,2-Trifluoroethylisothiocyanate (6 ml.) was added to 2-amino-6-chloropyrazine (6 g.) in acetonitrile (50 ml.) and the mixture heated under reflux on the steam bath for 6 hours. On cooling the precipitated solid was recrystallized from toluene to give 2-chloro-6-(3-[2,2,2-trifluoroethyl]thioureido)pyrazine, m.p. 170°-172°.

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

Reference:
Patent; Imperial Chemical Industries PLC; US4451463; (1984); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem