Month: January 2021

These common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, 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. Quality Control of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine

2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (323 mg, 1.08 mmol) was dissolved in 5 mL of N, N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N, N, N’, N’-tetramethyluronium hexafluorophosphate (614 mg, 1.63 mmol), 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 4c (200 mg, 1.63 mmol) and N, N-diisopropylethylamine (0.4 mL, 2.16 mmol). After stirring for 12 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 4-[[3-(6,8-dihydro-5H-imidazo[1,2-a]pyrazine-7-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 4 (10 mg, yield 2.3%) as a white solid. MS m/z (ESI): 404.1 [M+1] 1H NMR (400 MHz, CDCl3): delta 10.07 (br. s, 1H), 8.53 (d, 1H), 7.96 (m, 1H), 7.83 (m, 3H), 7.51 (m, 1H), 7.30 (m, 2H), 6.01 (t, 1H), 4.73 (d, 2H), 4.35 (s, 2H), 1.60 (m, 2H), 1.34 (m, 2H)

The synthetic route of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Co., Ltd.; TANG, Pengcho; LI, Xin; LI, Xiangqin; CHEN, Yang; WANG, Bin; ZHU, Zhe; EP2604610; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 21943-12-4, name is 2-Amino-3-bromopyrazine, 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 21943-12-4, Recommanded Product: 21943-12-4

A suspension of 2-amino-3-bromopyrazine (2.5 g, 19.3 mmol) in DME (20 mL) was added 3-bromo-1, 1, 1-trifluoroacetone (13.7g, 72.Ommol) and 4A molecular sieves (1.0 g). The reaction mixture was then stined at 90 C for 4h and quenched by the addition of water (25mL).This mixture was extracted with ethyl acetate. The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to give 8-chloro-2-trifluoromethyl-imidazo [1,2-a] pyrazine (0.8g, 25%). ?H NMR (400 MHz, CDC13): oe 8.13- 8.10 (m, 2H), 7.84-7.82 (m, 1H); LC-MS: 268.3.0 [M+2Hj.

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-Amino-3-bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; KOTRABASAIAH UJJINAMATADA, Ravi; PANDIT, Chetan; (152 pag.)WO2016/185342; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63286-28-2, 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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, This compound has unique chemical properties. The synthetic route is as follows.

2-Chloro-3-hydrazinylpyrazine (710 mg, 0.49 mmol) obtained by the method described in WO2008/130951 was dissolved in acetonitrile (12 mL), and 1,1′-carbonyldiimidazole (1.6 g, 9.8 mmol) was added thereto, and then, the resulting mixture was stirred at room temperature for 4 hours. To the reaction mixture, water was added, and the deposited solid was collected by filtration, whereby the title Compound R7 (117 mg, yield: 14%) was obtained. 1H-NMR (400 MHz, DMSO-d6, delta): 13.2 (br s, 1H), 7.93 (d, J=4.0 Hz, 1H), 7.34 (d, J=4.0 Hz, 1H)

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

Reference:
Patent; KYOWA HAKKO KIRIN CO., LTD.; ISHIDA, Hiroshi; MOTOSAWA, Keiichi; MIURA, Yusuke; NAKAI, Ryuichiro; OKADA, Ryoko; TAKAHASHI, Yuichi; (45 pag.)US2016/168125; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, 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 27825-20-3, Recommanded Product: Methyl 3-Hydroxy-2-pyrazinecarboxylate

Reference Example 27 0.30 g of methyl 3-hydroxy-2-pyrazinecarboxylate was dissolved in 1.5 ML of dimethyl sulfoxide, and thereafter, 0.70 ML of triethylamine and 0.54 g of L-aspartic acid diethyl ester hydrochloride were successively added thereto, followed by stirring at room temperature for 8 hours.. After chloroform and water were added to the reaction solution, the mixture was adjusted to PH 2 with 2 mol/L hydrochloric acid, and the organic layer was separated.. The obtained organic layer was washed with water and then dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure.. Toluene and n-hexane were added to the obtained residue, and the precipitate was collected by filtration, so as to obtain 0.18 g of diethyl (2S)-2-{[(3-hydroxy-2-pyrazinyl)carbonyl]amino} butanedioate.1H-NMR(CDCl3)delta: 1.27(3H,t,J=7.2Hz), 1.30(3H,t,J=7Hz), 2.94(1H,dd,J=4.4,17.2Hz), 3.15(1H,dd,J=4.8,17.2Hz), 4.14-4.23(2H,m), 4.24-4.32(2H,m), 4.99-5.02(1H,m), 8.15(1H,d,J=2.6Hz), 8.40(1H,d,J=1.5Hz), 8.78(1H,d,J=5.9Hz), 12.4(1H,brs)

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; TOYAMA CHEMICAL CO., LTD.; EP1417967; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 939412-86-9, SDS of cas: 939412-86-9

At 0C To a solution of (3-chloropyrazin-2-yl) methanamine hydrochloride (compound 102) (2.48 g, 13.8 mmol, 1.0 equiv.) In dichloromethane (80 mL) was added triethylamine (5.58 g, 55.2 mmol , 4.0 equivalents) and ((benzyloxy) carbonyl) -L-proline (compound 103) (3.43 g, 13.8 mmol, 1.0 equiv) Stirred at 0 & lt; 0 & gt; C for 15 minutes, A solution of 2- (7-azobenzotriazole) -N, N, N ‘, N’-tetramethyluronium hexafluorophosphate (HATU, 5.50 g, 14.5 mmol, 1.05 equiv) was added and the reaction was allowed to react at 0 C to room temperature for 5 minutes. The reaction solution was diluted with dichloromethane (200 mL), washed successively with ammonium chloride solution (200 mL x 1), saturated sodium bicarbonate solution (200 mL x 1), saturated brine (200 mL x 1), and the organic phase was washed with anhydrous sulfuric acid The sodium was dried, filtered, the filtrate was dry and the residue was purified by column chromatography (eluent: Dichloromethane: methanol = 80: 1) to give benzyl (S) -2 – (((3-chloropyrazin-2-yl) methyl) carbamoyl) pyrrolidine-1-carboxylate (2.85 g , Yield: 55.1%). Light brown oil;

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; Dongguan Zhen Xing Beite Pharmaceutical Co., Ltd.; Cai Xiong; Zhong Xianbin; Ye Chunqiang; He Qijie; Tan Shifeng; Qian Changgeng; (44 pag.)CN106588937; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 54608-52-5,Some common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, molecular formula is C4H6N4, 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 sample of 2-hydrazinopyrazine was prepared from 2-chloropyrazine and hydrazineusing a procedure analogous to that described in the literature [P.J. Nelson and K.T. Potts, /. Org. Chem.,27. 3243 (1962)], except that the crude product was extracted into 10% methanol/dichloromethane andfiltered, and the filtrate was concentrated and purified by flash chromatography on silica gel, eluting with100% ethyl acetate followed by 10% methanol in dichloromethane. A mixture of 2-hydrazinopyrazine(820 mg, 7.45 mmol), trifluoroacetic acid (2.55 g, 22.4 mmol), and polyphosphoric acid (10 mL) washeated to 140 C with stirring for 18 h. The solution was added to ice and neutralized by the addition ofammonium hydroxide. The aqueous solution was extracted three times with ethyl acetate, washed withbrine, and dried over anhydrous magnesium sulfate. Concentration followed by flash chromatography(silica gel, 1:1 hexane:ethyl acetate, then 100% ethyl acetate) afforded the title compound as a solid.’H NMR (500 MHz, CDC13): 5 8.17-8.20 (m, 2H), 9.54 (s, 1H); C/MS 189 (M+l).

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/23750; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6905-47-1, These common heterocyclic compound, 6905-47-1, name is 2-Amino-6-methoxypyrazine, 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 (9S)-2-(2-methylpyridin-4-yl)-7,8,9,10-tetrahydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine (0.6 g, 2.253 mmol) in Tetrahydrofuran (THF) (30 mL) stirred under nitrogen at room temperature was added triethylamine (1.884 mL, 13.52 mmol) and triphosgene (0.669 g, 2.253 mmol). Then reaction mixture was stirred at room temperature for 30 minutes. 6-methoxypyrazin-2-amine (0.846 g, 6.76 mmol) was added at rt. Then the reaction mixture was stirred at 65 C. for 16 hr. The reaction mixture was cooled to room temperature and concentrated under reduced pressure and was partitioned between water (20 mL) and EtOAc (50 mL). Organic layer was separated and was dried over anhydrous Na2SO4, filtered and filtrate was evaporated to give crude as brown solid (TLC eluent: 100% EtOAc: Rf-0.3; UV active). The crude was purified by column chromatography using neutral alumina and was eluted with 50% EtOAc in Hexane to afford pure (9S)-N-(6-methoxypyrazin-2-yl)-2-(2-methylpyridin-4-yl)-8,9-dihydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine-10(7H)-carboxamide (0.220 g, 0.526 mmol, 23.34% yield) as a off-white solid, LCMS (m/z): 418.3 [M+H]+. 1H NMR (400 MHz, CDCl3): delta 13.64 (s, 1H), 9.45-8.78 (m, 1H), 8.60 (dd, J=5.3, 0.8 Hz, 1H), 7.96 (d, J=0.5 Hz, 1H), 7.80 (ddd, J=5.3, 1.7, 0.7 Hz, 1H), 7.62 (dt, J=1.8, 0.7 Hz, 1H), 7.59 (s, 1H, 7.57 (s, 1H), 7.46 (d, J=8.0 Hz, 1H), 5.04 (t, J=2.6 Hz, 1H), 3.84 (s, 3H), 3.57-3.26 (m, 3H), 3.15-2.91 (m, 1H), 2.64 (s, 3H), 2.28 (d, J=14.3 Hz, 1H), 2.12-1.85 (m, 1H), 1.43 (s, 2H)

Statistics shows that 2-Amino-6-methoxypyrazine is playing an increasingly important role. we look forward to future research findings about 6905-47-1.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-28-4, A common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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 4 N-(6-Chloro-pyrazin-2-yl)-2,7-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 7.5 g (26 mmols) of methyl 2,7-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 4.36 g (33 mmols) of 2-amino-6-chloro-pyrazine were reacted in 40 ml of xylene and worked up analogous to Example 2. 7.2 g (73percent of theory) of N-(6-chloro-pyrazin-2-yl)-2,7-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were obtained. IR (KBr): 1645 cm-1 (CO amide).

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

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
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 23611-75-8 as follows. Formula: C6H5ClN2O2

A suspension of methyl 6-chloropyrazine-2-carboxylate (3.4 g, 19.7 mmol) in THF (100 mL) was cooled to below 10 C and treated dropwise with 3M MeMgBr (Et20, 13.13 mL, 39.4 mmol), maintaining the reaction temperature below 10 C. The reaction mixture was then allowed to warm to RT. After 1 hr, the reaction mixture was concentrated then taken up in 1M HCI (aq, 150 mL) and extracted with EtOAc (3 x 70 mL). The organic layers were combined, dried (Mg504), filteredand concentrated on to silica (4 g). The crude product was purified by chromatography on silica gel (40 g column, 20-70% EtOAc/iso-hexane) to afford 2-(6-chloropyrazin-2-yl)propan-2-ol (1 .4 g, 7.71 mmol, 39% yield) as an orange oil; Rt 1.30 mins (HPLC acidic); mlz 173 (M+H) (ES); 1H NMR (500 MHz, DMSO-d6) 6 8.87 (d, J = 0.5 Hz, 1 H), 8.67 (d, J = 0.5 Hz, 1 H), 5.61 (s, 1 H), 1.46 (s, 6H).

According to the analysis of related databases, 23611-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STEP PHARMA S.A.S.; QUDDUS, Abdul; NOVAK, Andrew; COUSIN, David; CHATZOPOULOU, Elli; BLACKHAM, Emma; JONES, Geraint; THOMAS, Jennifer; WRIGGLESWORTH, Joseph; DUFFY, Lorna; BIRCH, Louise; GEORGE, Pascal; AHMED, Saleh; (277 pag.)WO2019/106156; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-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 313339-92-3, category: Pyrazines

5-Chloro-2-fluoro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (709 mg) was added to a reaction vessel containing a magnetic stirring bar together with 3,5-dichloro-pyrazine-2-carbonitrile (300 mg), 1,1-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (Pd(dppf)2Cl2) (100 mg) and cesium carbonate (1.69 g), followed by 6 ml dioxane and 1 ml water, and the mixture heated to 100 00 under stirring. After 3 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (40 ml) and extracted with EtOAc (3 x 80 ml). The combined aqueous phases were dried over sodium sulfate, filtered and evaporated to afford the crude product as a brown oil. Purification by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent afforded 5-chloro-N-[4-(6-chloro-5-cyano-pyrazin-2-yl)-phenyl]- 2-fluoro-benzenesulfonamide as a brown foam after evaporation of the solvents under reduced pressure. Yield: 160 mg (22%). MS (ES-): m/e = 421.0 (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, 3,5-Dichloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; NAZARE, Marc; HALLAND, Nis; SCHMIDT, Friedemann; WEISS, Tilo; DIETZ, Uwe; HOFMEISTER, Armin; WO2013/41502; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem