Month: August 2021

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., SDS of cas: 27825-21-4

[577] Step A: 3-mercapto-pyrazine-2-carboxylic acid methyl ester [578] After 3-chloro-pyrazine-2-carboxylic acid methyl ester (0.4 g, 2.3 mmol)was dissolved in MeOH (46 mL), sodium hydrosulfide monohydrate (0.65 g, 6.9mmol) was added thereto, and the mixture was stirred at room temperature for 9hours. After the termination of the reaction, the reactant was concentratedunder reduced pressure, and 1N HCl aqueous solution was used to adjust the pHof the reactant to 3. The reactant was extracted with EtOAc, and the organiclayer was separated to obtain the title compound (0.35 g, 89%).[579] 1H-NMR (CDCl3) delta 8.43(1H, m), 8.42(1H, m),5.18(1H, brs), 4.04(3H, s)

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; LG LIFE SCIENCES LTD.; KIM, Young Kwan; KIM, Myoung Yeol; PARK, Sang Yun; PARK, Ok Ku; ARTEMOV, Vasily; LEE, Sang Dae; JOO, Hyun Woo; CHOI, Eun Sil; WO2014/69963; (2014); 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 768-05-8 as follows. Application In Synthesis of Pyrazinoic acid hydrazide

General procedure: A mixture of compound 12/13 (1mmol) and hydrazine derivative (1mmol) was taken in ethanol (10mL) in a dry 50mL RB flask. A catalytic amount of conc. H2SO4 was added and the mixture was stirred for 10-15min at RT. After the complete consumption of both starting materials (monitored by TLC), the reaction mixture was poured into ice cold water (10mL). The solid separated was filtered off under suction and washed with ethanol and water.

According to the analysis of related databases, 768-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reddyrajula, Rajkumar; Dalimba, Udayakumar; Madan Kumar; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 263 – 282;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 912773-24-1, These common heterocyclic compound, 912773-24-1, name is 6-Bromoimidazo[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.

Step 1 : To a solution of 6-bromoimidazo [1, 2-a] pyrazine (30 g, 151 mmol) in toluene (400 mL) were sequentially added Cs2C03 (123 g, 378 mmol), 4-(ethoxycarbonyl)phenylboronic acid (35.2 g, 181 mmol) and Pd(dppf)2Cl2 (3.70 g, 4.50 mmol). The reaction mixture was stirred at 90 C for 12 h under argon atmosphere then, was filtered through celite. The filtrate was concentrated and the residue was purified the by flash column chromatography (silica gel, eluent n-hexane/EtOAc 70:30) to afford ethyl 4-(imidazo [1, 2-a]pyrazin-6-yl)benzoate (16 g, 39%) as yellow solid. 1H NMR (400 MHz, DMSO-i 6) 5: 9.35 (s, IH), 9.17 (s, IH), 8.15 (d, J= 8.4 Hz, 2H), 8.03 (d, J= 8.4 Hz, 2H), 7.88 (s, IH), 7.79 (s, IH), 4.32 (q, J= 6.8 Hz, 2H), 1.44 (t, J = 7.2 Hz 3H); MS (ESI) m/z 268 [C,5H13N302 ^H] “.

The synthetic route of 912773-24-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 486424-37-7, 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 486424-37-7 as follows.

HATU (3.54 g, 9.36 mmol) was added to a solution containing 1.64 g (7.5 mmol) of 3- amino-6-bromopyrazine-2-carboxylic acid in 25 mL of DMF. The reaction was stirred for 5 minutes before adding 2.5 mL (22.5 mmol) of N-methylmorpholine and 1.68 g (9.36 mmol) of 4- morpholinopyridin-3-amine. The reaction mixture was stirred for 16 h then quenched with 10 mL of saturated NH4C1 solution and then 10 mL of water. The mixture was extracted with EtOAc three times; the combined organics were washed with brine and then dried over a2S04. The solvent was then evaporated and the residue was chromatographed (0% to 20% CH3OH / dichloromethane) to afford compound Int lB-1 as a yellow solid

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SILVERBACK THERAPEUTICS, INC.; THOMPSON, Peter Armstrong; EDRIS, Badreddin; COBURN, Craig Alan; BAUM, Peter Robert; (372 pag.)WO2018/227023; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6905-47-1, 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. 6905-47-1, name is 2-Amino-6-methoxypyrazine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-methoxypyrazin-2-amine (3 g, 24 mmol) in dry DMF (35 mL), N-chlorosuccinimide (3.2 g, 24 mmol) was added. The reaction mixture was stirred at room temperature for 16 h then waspoured into ice and brine (130 mL). The aqueous solution was extracted with ethyl acetate (3 x 120 mL), the organic phase was washed with 5% solution of LiCI, dried over Na2SO4 and evaporated under reduced pressure. The crude was purified by SNAP-340-NH (cyclohexane/ethyl acetate from 95:5 up to 8:2) and by SNAP1 00-Si-OH (eluting with DCM)to afford the title intermediate (1.98 g, 12.5 mmol, 52% yield). LC-MS (M-H) = 160.1

The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-methoxypyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 486460-21-3, 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 486460-21-3 as follows.

Anhydrous DMF and N-ethyl-N-isopropylpropan-2-amine (20.88 mg, 0.162 mmol)were added to a mixture of HATU (28.7 mg, 0.075 mmol), HOAT (10.3 mg, 0.075 mmol), 1-(6-chloro-3-cyanoquinolin-4-yl)piperidine-4-carboxylic acid (17 mg, 0.054 mmol) and 3-(trifluoromethyl)-5 ,6,7, 8-tetrahydro- [1 ,2,4jtriazolo[4,3 -aj pyrazine (12.3 mg, 0.054 mmol).The mixture was stirred at room temperature for 6 hours. The reaction mixture was pouredinto 10 ml NaHCO3 aqueous solution, and the resulting suspension was stirred for 1 hour.The mixure was filtered and the filter cake was washed with water, and dried to afford the title compound.MS: 490 (M + 1). Human CYP8B1 1C50 (nM) 23.2

According to the analysis of related databases, 486460-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; DYKSTRA, Kevin, D.; HRUZA, Alan; LI, Derun; LIU, Hong; TANG, Haiqun; TAOKA, Brandon, M.; VERRAS, Andreas; WALSH, Shawn, P.; WU, Wen-Lian; (170 pag.)WO2018/34918; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1174321-06-2, 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. 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

5-(Difluoromethyl)pyrazine2carboxylic acid (30.0 g, 1.05 equiv) and (4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-fluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (49.2 g, 1.00 equiv.) were charged to a reactor and EtOAc (443 mL) was added to the mixture to give a suspension. A solution of T3P (105 g 1.10 equiv, 50 wt% in EtOAc) (Archimica, Germany) was added at ambient temperature while controlling the internal temperature below 30 C. The reaction mixture was stirred at 4045 C >3 hours and monitored by HPLC. The reaction mixture was cooled to ambient temperature and water (98 mL) was charged. After 1015 minutes charged 28% ammonium hydroxide (137 mL) while controlling the temperature below 30 C. Additional EtOAc (172 mL) was added and the reaction mixture was stirred for 30 minutes at ambient temperature. The aqueous phase was separated and backextracted with EtOAc (246 mL). The organic phases were combined and washed with 15% aq. NaCl (98 mL) and water (98mL). The organic layer was filtered over Celite (0.5 Wt) and concentrated under vacuum to obtain a beige solid (quantitative crude yield) which was recrystallized from 1propanol to afford N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-(difluoromethyl)pyrazine-2-carboxamide as a tan solid (54.2g).

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-(Difluoromethyl)pyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ???????????????????????????; ? Buranko; Kimu ?; Chan ?; ?; Yoshizawa Kazuhiro; (94 pag.)JP2016/121177; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 89123-58-0,Some common heterocyclic compound, 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, molecular formula is C4H5BrN4, 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.

(3-((tert-butyldimethylsilyl)oxy)-4-cyclohexyl-2-fluorophenyl)boronic acid (0.821 g, 2.33 mmol), 5-bromopyrazin-2-amine (0.40 g, 2.3 mmol), K2CO3 (0.659 g, 4.77 mmol), Pd(dppf)Cl2.CH2Cl2 (0.086 g, 0.12 mmol), deoxygenated toluene (10 mL), and deoxygenated deionized water (10 mL) was heated for 16 hours at 80 Celsius. The reaction mixture was then cooled to rt, diluted with dichloromethane (25 mL), and washed with brine (2×25 mL). The organic layer was dried over MgSO4, filtered, and concentrated to dryness to yield the title compound (0.936 g, 100%) which was used without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromopyrazine-2,3-diamine, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (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. 6863-73-6, name is 3-Chloropyrazin-2-amine, A new synthetic method of this compound is introduced below., SDS of cas: 6863-73-6

General procedure: Sodium hydride (60% in mineral oil, 0.04 g, 1 mmol) was addedto a stirred solution of benzyl alcohol derivative (1 mmol) inanhydrous N,N-dimethylformamide (3 mL of DMF) at room temperatureand stirring was continued for 1 h. 2-Amino-3-chloropyrazine (8b, 0.13 g, 1 mmol) was added to the reactionmixture and the reaction mixture was stirred at 100 C for 15 h.After cooling, the solvent was evaporated and the residue waspartitioned betweenwater and dichloromethane. The organic layer was dried over sodium sulfate anhydrous, filtered, and concentrated.The residue was purified by column chromatography (SiO2,EA/n-Hex 1/5). 4.1.2.1 3-(Benzyloxy)pyrazin-2-amine (9g) Yellow solid, yield: 53.8%, 1H NMR (400?MHz, CDCl3) delta?=?5.45 (2H, s, OCH2Ph), 6.20 (2H, br, NH2), 7.38-7.48 (7H, m, ArH). Reported [ 48,49].

The synthetic route of 6863-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elkamhawy, Ahmed; Park, Jung-eun; Hassan, Ahmed H.E.; Pae, Ae Nim; Lee, Jiyoun; Park, Beoung-Geon; Roh, Eun Joo; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 529 – 543;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 87486-34-8, These common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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.

3,5-Dibromo-l-methyl-lH-pyrazin-2-one (1.Og, 3.73 mmol) and 4- amino-2-nitrobenzoic acid (0.68g, 3.73 mmol) are dissolved in isopropanol (20 mL) and heated at 9O0C for 4 hours. The reaction is cooled to room temperature and the resulting suspension is filtered. The filter cake is then washed with ethyl ether (3 x 10OmL) and air dried to give 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2- ylamino)-2-nitro-benzoic acid (3) as a tan solid (1.17g).

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; WHITNEY, James A.; DI PAOLO, Julie; VALLECA, Mark A.; BRITELLI, David R.; CURRIE, Kevin S.; DARROW, James W.; KROPF, Jeffrey E.; LEE, Tony; GALLION, Steven L.; MITCHELL, Scott A.; PIPPEN, Douglas A.I.; BLOMGREN, Peter A.; STAFFORD, Douglas Gregory; WO2008/33858; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem