Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 69214-33-1, name is 8-Chloroimidazo[1,2-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 69214-33-1, Application In Synthesis of 8-Chloroimidazo[1,2-a]pyrazine

To a mixture of 8.-chIoroirnidazo[12.-a]pyrazinc (500 mg, 3.3 rnrnol) in AcOH (5 mL) was added Br2 (800 mg, 5.0 mmol) at RT. The resulting mixture was stirred at RT for 2 days, then poured into water (20 mL) and extracted with EtOAc (15 mL x 3). The combined organic layer was washed with aqueous sodium bicarbonate solution and brine, dried over MgSO,filtered and concentrated in vacuo. The residue was purified by chromatography on silica (9.?16% EtOAc in petroleum ether) to give the title compound (30() mg) as a yellow solid. LRMSm/z (M+H) 232.2, 234.1 found, 231.2, 234.1 required.

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; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 41110-29-6 as follows. COA of Formula: C7H8N2O2

To a stirred solution of the product of Step A (0.9 g, 5.9 mmol) in MeOH (20 mL) was added hydrazine hydrate (1.5g, 23.7 mmol) at RT. The mixture was stirred at 60 C overnight. The mixture was concentrated and the residue was dissolved into EA (30 mL) . The organic phase was washed with brine, dried over Na2SO4and concentrated under reduced pressure. The residue (460 mg, yield: 51.1%) was used into next step directly. MS: M/e 153 (M+1)+.

According to the analysis of related databases, 41110-29-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; SUN, Hanzi; ZHOU, Changyou; (253 pag.)WO2020/20097; (2020); 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. 22047-25-2, name is Acetylpyrazine, A new synthetic method of this compound is introduced below., Formula: C6H6N2O

Preparation 21-Pyrazin-2-yl-ethylamineThe synthetic procedure used in this preparation is outlined below in Scheme C. To a solution of 1-pyrazin-2-yl-ethanone (2.0 g, 15.85 mmol) and ammonium acetate (19.337 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 11.1 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH=13. The aqueous solution was extracted with dicholromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 14.62 g of 1-pyrazin-2-yl-ethylamine, yield: 75%. MS (M+H)=124.

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; Chen, Li; Dillon, Michael Patrick; Feng, Lichun; Yang, Minmin; US2010/324069; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 16298-03-6, The chemical industry reduces the impact on the environment during synthesis 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, I believe this compound will play a more active role in future production and life.

Example 1 ; 3-Methyl-6-(4-(methvlsulfonvl)phenyl)-iV-phenvlpvrazine-2-carboxamide (Compound IV-1)SMETHOD A:Step 1: Methyl 3-amino-6-bromopyrazine-2-carboxylate [00141] 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 RT for 16 hours. The resultant precipitate was filtered, washed with MeCN and dried to give the desired product as a yellow solid (11.68 g, 92% 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.

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 2-aminopyrazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus Alphonsus; VIRANI, Aniza, Nizarali; REAPER, Philip, Michael; WO2011/143425; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-80-1, These common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, 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.

A solution of 5-chloropyrazine-2-carboxylic acid (200.0 g, 1.26 mol) in THF (2.5 L) was treated with a solution of tert-butyl 2,2,2-trichloroacetimidate (460 mL, 2.57 mol) in cyclohexane (2.5 L). The reaction was stirred at 25 C for 5 min and then treated with boron trifluoride dimethyl etherate (144.0 mL, 126 mmol). The resulting reaction mixture was stirred at 25 C for 16 h and then diluted with EtOAc (5.0 L), washed with a saturated aqueous sodium bicarbonate solution (4.0 L) followed by water (5.0 L). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (Silica 60-120 mesh, 10% EtOAc in hexanes) to give tert-butyl 5-chloropyrazine-2-carboxylate (250 g, 92%) as a colorless oil. MS (ESI, positive ion) m/z: 215.2 (M+1 )+. 1H NMR (400 MHz, CDCl3) delta 9.01 (d, J = 1.3 Hz, 1 H), 8.70 (d, J = 1.3 Hz, 1 H), 1.66 (s, 9H).

Statistics shows that 5-Chloropyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 36070-80-1.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 36070-75-4, A common heterocyclic compound, 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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.

A mixture of A-5 (1.5 g, 10.75 mmol) and 5% Pd/C (150 mg) in TFA (15 mL, 201.94 mmol) and (2,2,2-trifluoroacetyl) 2,2,2-trifluoroacetate (8 mL, 57.55 mmol) was stirred under H2 (15 psi) at 20 C for 5 hours. The mixture was filtered through Celite, eluted with EtOAc (20 mL), and concentrated to a residue. The residue was diluted with H20 (30 mL) and sat.Na2C03 (30 mL) and extracted with EtOAc (50 mL x 2). The combined organic phase was washed with water (20 mL x 2) and brine (20 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by flash chromatography on silica gel (EtOAc in PE = 20% to 30% to 50%) to afford A-21 (2100 mg, 8.72 mmol) as a solid. 1H NMR (400MHz, CDCls) deltaalpha = 8.58 (d, 1H), 8.43 (s, 1H), 7.38 (br s, 1H), 4.71 (d, 2H). LCMS R, = 0.61 min using Method B, MS ESI calcd. for C7H6C1F3N30 [M+H]+ 240.0, found 239.9.

The synthetic route of 36070-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (141 pag.)WO2018/98491; (2018); 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. 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H5ClN2O2

To a solution of the product from step 1 (100 mg, 0.58 mmoi) in toluene (2 mL) was added Pd(PPh3)4 (134 mg, 0.12 mmol) and 2ttributylstannyl)pyridine (213 mg, 0,58 mrnol) at room temperature and the resulting mixture heated to 100 C overnight. After cooling to RI, the mixture was filtered and 5 rnL of aq. KF solution was added to the filtrate. The resulting mixture was stirred for 30 mins and extracted with EtOAc (5 mL x3). The combined organic layerswere washed with brine, dried over Na2504, filtered and concentrated in vacuo, The residue was purified by chromatography (30% EtOAc in petroleum ether) to provide the title compound as a oil. LRMS nih (M-f-H) 216.1 found, 216,1 required.

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 27825-21-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 89123-58-0, These common heterocyclic compound, 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, 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.

5-Bromopyrazine-2,3-diamine (27) was preparedfrom 2-amino-3,5-dibromopyrazine and NH4OH (25%) in sealedtube according to lit.33 1H-NMR delta ppm (CD3OD): 4.90 (s,4H,NH2),7.24 (s,2H,H-5,6). 13C-NMR (CD3OD): 123.3, 129.8, 144.3, 145.9. MS(ESI+) m/z: 189(M + H, 100%), 191(M + H+2, 97%). 27 (0.303 g,1.6 mmol) in EtOH (10 mL) was reduced by hydrogenation using 40psi of H2 and 10% Pd-C (15 mg) for 8 h. The catalyst was filtered ona bed of Celite, the filtrate was concentrated in vacuo. Purplecolored powder 28 were used for the further steps without purification.1H-NMR delta ppm (CD3OD): 4.90 (s,4H,NH2), 7.24 (s,2H, H-5,6). 13C-NMR (CD3OD): 123.7, 145.1. MS (ESI) m/z: 110(M + H,100%). 29 was prepared from 28 (0.11 g) and Na2S2O5 adduct of 4-(morpholin-4-ylcarbonyl) benzaldehyde (0.323 g) as described ingeneral method. Resulting precipitate (0.155 g) was purified withcolumn chromatography using CH2Cl2: MeOH (95 : 5) as eluant,yield 0.056 g, (18%), mp > 300 C. 1H-NMR delta ppm (DMSO-d6+D2O):3.27-3.61 (m,8H), 7.62 (d,2H,J – 8.4 Hz), 8.33 (d,2H,J – 8.4 Hz), 8.40(s,2H,H-5,6). 13C-NMR (DMSO-d6+D2O): 66.0, 127.3, 127.8, 129.9,138.2, 139.0, 154.7, 168.2. MS (ESI) m/z: 310(M + H, 100%). AnalCalcd for C16H15N5O2H2O: C, 58.70; H, 5.23; N, 21.39. Found: C,58.97; H, 5.01; N, 20.91.

Statistics shows that 5-Bromopyrazine-2,3-diamine is playing an increasingly important role. we look forward to future research findings about 89123-58-0.

Reference:
Article; Karaaslan, Cigdem; Doganc, Fatima; Alp, Mehmet; Koc, Asli; Karabay, Arzu Zeynep; Goeker, Hakan; Journal of Molecular Structure; vol. 1205; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 32587-10-3, These common heterocyclic compound, 32587-10-3, name is 3-Aminopyrazine-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.

EXAMPLE 3 Synthesis of 3-Aminopyrazine-2-carbonitrile (Intermediate 2) To a solution of intermediate 1 (3.5 g, 25 mmol) in DMF (40 mL) at RT was added POCl3 (4.5 mL, 49 mmol) slowly. The resulting mixture was heated at 80 C. for 15 min and then cooled to RT. The mixture was poured into ice water and the mixture neutralized with 10% NaOH solution. The resulting solid was filtered and redissolved in 5% HCl. The solution was heated at 70 C. for 30 min and the resulting solid filtered. After thoroughly washed with water, the title compound was obtained as a brown solid (1.7 g, 56%). 1H NMR (500 MHz, DMSO-d6): delta 8.28 (d, J=2.4 Hz, 1H), 7.90 (d, J=2.4 Hz, 1H), 7.32 (br s, 2H). MS (ES+): m/z 121 (M+H)+.

Statistics shows that 3-Aminopyrazine-2-carboxamide is playing an increasingly important role. we look forward to future research findings about 32587-10-3.

Reference:
Patent; TargeGen, Inc.; US2007/259876; (2007); 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Chloropyrazine-2-carbonitrile

2- cyano-3-(4-oxopiperidino)-pyrazine (Compound 56a)A mixture of 2-cyano-3-chloropyrazine (500 mg, 3.4 mmol), piperidin-4-one hydrochloridre monohydrate (1.33 g, 8.5 mmol) and TEA (1.8 ml, 10.3 mmol) in toluene (20 ml) was reacted at 80C for 8 h. After diluting with H20 and EtOAc, the organic phase was evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (Horizon TM – Biotage) eluting with PE – EtOAc 80:20, affording a yellow solid. Yield: 69%.MS: [M+H]+ = 203.15

The synthetic route of 55557-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RECORDATI IRELAND LIMITED; LEONARDI, Amedeo; MOTTA, Gianni; RIVA, Carlo; GUARNERI, Luciano; GRAZIANI, Davide; MARINONI, Fabio; BETTINELLI, Ilaria; WO2011/29633; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem