Month: July 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., HPLC of Formula: C6H5ClN2O2

EXAMPLE II-23 In 15 mL of acetonitrile was dissolved 0.3 g of methyl 3-chloro-2-pyrazinecarboxylate. At an ice-cooled temperature, 10% fluorine gas (a fluorine gas diluted with nitrogen gas) was introduced at a rate of 45 ml per minute for a period of 18 minutes. Then, while elevating the temperature from the ice-cooled temperature to room temperature, nitrogen gas was introduced for one hour, and the reaction product was concentrated under reduced pressure. The oily product thus obtained was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=10:1] to obtain 0.03 g of methyl 3-chloro-6-fluoro-2-pyrazinecarboxylate as a colorless oily product. IR (neat) cm-1: 1736 1H-NMR (CDCl3) delta: 4.04(3H,s), 8.43(1H,d,J=8.3 Hz)

According to the analysis of related databases, 27825-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (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. 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Dichloro-6-ethylpyrazine-2-carboxamide

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (3a,503 mg, 2.29 mmol), 2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (699 mg, 2.30 mmol), DIPEA (0.78 mL, 4.56 mmol) and 1,4-dioxane (10 mL) was stirred at 110 C for 25 h. After the mixture was cooled to room temperature, saturated aqueous NaHCO3 solution was added, and the resulting slurry was extracted with CHCl3. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (CHCl3/MeOH/28% aqueous NH3=100:0:0 to90:9:1). The resulting product was washed with EtOAc, filtered and dried in vacuo at 50 C to give 9 (701 mg, 63%) as an orange solid. 1HNMR (DMSO-d6): delta 1.25 (3H, t, J=7.4 Hz), 1.43-1.59 (2H, m),1.77-1.91 (2H, m), 2.14 (3H, s), 2.20-2.72 (11H, m), 2.79 (2H, q,J=7.5 Hz), 3.64-3.75 (2H, m), 3.85 (3H, s), 6.51 (1H, dd, J=2.4, 8.8 Hz), 6.65 (1H, d, J=2.4 Hz), 7.83 (1H, d, J=1.6 Hz), 8.04 (1H, d,J=8.8 Hz), 8.12 (1H, d, J=1.6 Hz), 11.11 (1H, s); MS (ESI) m/z[M+H]+ 488.

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:
Article; Iikubo, Kazuhiko; Kurosawa, Kazuo; Matsuya, Takahiro; Kondoh, Yutaka; Kamikawa, Akio; Moritomo, Ayako; Iwai, Yoshinori; Tomiyama, Hiroshi; Shimada, Itsuro; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1683 – 1692;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 173290-17-0, name is Methyl 3-iodopyrazine-2-carboxylate, 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 173290-17-0, SDS of cas: 173290-17-0

3-Iodopyrazine-2-carboxylic acid methyl ester (0.37 g, 1.4 mmol, Reference compound No.15-1), 4-pyridinemethanethiol hydrochloride (0.24 g, 1.5 mmol) and potassium carbonate (0.41 g, 3.0 mmol) were suspended in N,N-dimethylformamide (10 mL), then the mixture was stirred at 60C for 1 hour. The reaction mixture was diluted with ethyl acetate (70 mL), and washed with water (100 mL) twice and brine (70 mL) twice. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was filtered off with diisopropyl ether to give 0.25 g of the title reference compound as a pale cinnabar solid. (Yield 69%)1H-NMR(500MHz,CDCl3)delta 4.03(s,3H),4.37(s,2H),7.35(dd,J = 4.3,1.5 Hz,2H),8.39(d,J = 2.1 Hz,1H), 8.52(dd,J = 4.3,1.5 Hz,2H),8.53(d,J = 2.1 Hz,1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-iodopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SANTEN PHARMACEUTICAL CO., LTD.; EP1602647; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 762240-92-6, A common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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.

General procedure: To the stirred reaction mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazine hydrochloride(11) (300 mg, 1.32 mmol), TEA (0.55 mL, 3.95 mmol)and toluene (10 mL), substituted cyanates 12(a-e)/isocyanates12(f-j) (1.32 mmol) were added at ambient temperature.The reaction mass was agitated at 75-80 C until thecompletion of the reaction that was monitored by TLC. Thereaction mass was allowed to cool at ambient temperatureand it was washed sequentially with 3% aqueous HCl(5.0 mL) and then water (5.0 mL). The organic fraction wasconcentrated under vacuum at 50-55 C to obtain crudeproduct. It was purified by column chromatography using10-50% of EtOAc:hexane mixture as a mobile phase.

The synthetic route of 762240-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 41270-66-0, These common heterocyclic compound, 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, 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.

In a 10 liter reactor, 2 liters of isopropylamine and 222 g of SLP-3 were added and the reaction was stirred at room temperature for 48 hours until the reaction was completed.Add 5 liters of ethyl acetate and 3 liters of water to stir, and let stand for phase separation; the organic phase is washed with dilute hydrochloric acid, water and saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated to obtain crude product; crude product is ethyl acetate. Recrystallization from petroleum ether gave 205 g of white solid SLP-4.Yield: 85%.1H NMR (400 MHz, CDCl3): delta 7.89 (s, 1H), 7.43-7.22 (m, 10H), 4.59 (d, 1H), 4.08 (m, 1H), 1.30 (d, 6H)ESI/MS+(m/z):289

The synthetic route of 41270-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Aikangrui Pharmaceutical Technology Co., Ltd.; Fan Linfeng; Zhu Yangwei; Qiu Aiyun; Lv Bojie; Xu Zhonghui; Zhang Changxuan; (11 pag.)CN106316967; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4, The chemical industry reduces the impact on the environment during synthesis 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, I believe this compound will play a more active role in future production and life.

The compound obtained in Step 4 (53 mg) was dissolved in chloroform (2 mL), trifluoroacetic acid (0.2 mL) was added and stirred overnight at room temperature. The oil obtained reaction solution by concentration under reduced pressure was dissolved in N, N- dimethylformamide (1.5 mL), Was stirred for 2 hours at 200 C. was added cesium carbonate (111 mg) and 4-fluoro-2- (trifluoromethyl) benzonitrile (64 mg). To the reaction solution was extracted 3 times with ethyl acetate after addition of water, The organic layer was washed with water and saturated brine, Dried and concentrated with sodium sulfate. The resulting residue to give the title compound purified by silica gel column chromatography (19mg, 30%). LRMS (ESI) m / z 372 [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, tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

13134-38-8, name is 3,6-Dimethylpyrazin-2-amine, 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. Computed Properties of C6H9N3

[0090] To a stuffed solution of 53 mg (0.427 mmol) of furan-2,5-dicarbaldehyde and 111 mg (0.90 1 mmol) of 3,6-dimethylpyrazin-2-amine in 5 mL of DCE was added 100 tL of acetic acid and approximately 500 mg of anhydrous Na2504. After 30 mm at rt under argon, the mixture was treated with 386 mg (1.82 mmol) of sodium triacetoxyborohydride, then was stirred further for 48 h. The mixture was treated with water (– 3 mL), excess satd. aq. NaHCO3, and EtOAc, and was stuffed an additional 1 h at rt. The mixture was extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried over Na2504, and concentrated in vacuo. Purification by preparative TLC (90% EtOAc/hexanes) provided 10 mg of the title compound. MS (ESj: [M + H] 339.3; [M+Na] 361.4; MS (ES): EM-H] 337.4. ?H NMR: (500 MHz, CDC13) oe 7.62 (2H, s), 6.2 (2H, s), 4.63 (4H, d, J= 5 Hz), 4.55 (2H, br s), 2.35 (6H, s), 2.31 (6H,s). Also obtained was (5- (((3 ,6-dimethylpyrazin-2-yl)amino)methyl)furan-2-yl)methanol as a side product (See Example 8).

The synthetic route of 13134-38-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROPORE THERAPIES, INC.; WRASIDLO, Wolfgang; STOCKING, Emily, M.; (53 pag.)WO2016/40780; (2016); 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. 1458-16-8, name is Methyl 3-amino-6-iodopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H6IN3O2

30 ml of ammonia in water is added under magnetic stirring to 15 g (53.8 mmol) of a solution of methyl 3-amino-6-iodopyrazine-2-carboxylate in 150 ml of methanol. The reaction medium is stirred at 25C for 48 hours. After evaporation of the solvents, the precipitate obtained is filtered, rinsed with water and then dried at 50C to yield 12.50 g of 3-amino-6-iodopyrazine-2-carboxamide (88%) in the form of a beige solid. LCMS (EI, m/z): (M+1) 265.02 1H NMR: deltaH ppm (400 MHz, DMSO): 8.35 (1H, s, CHarom), 7.85 (1H, bs, NH), 7.60 (3H, bs, NH), 3.25 (3H, s, CH3)

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 1458-16-8.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Kruczynski, Anna; Creancier, Laurent; Kaloun, El Bachir; Bedjeguelal, Karim; Rabot, Remi; EP2689779; (2014); 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. 356783-16-9, name is 3,6-Dichloropyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3,6-Dichloropyrazine-2-carbonitrile

KF2H2O (1.3 g, 6 eq) and TBAB (tetrabutylammoniumbromide) (0.3 g, 0.4 eq) were added into the mixed solventcontaining 4 mL of DMSO and 8 mL of toluene. Thetoluene was subsequently removed by distillation underreduced pressure. A further 8 mL of toluene was thenadded and once again removed by distillation underreduced pressure with the purpose of removing the moisture of the reagent relating to the reaction. Then, 3,6-dichloropyrazine-2-carbonitrile (0.4 g, 1 eq) was addedand the mixture was stirred at 50 C for 3 h. Subsequently,anhydrous K2CO3 (0.04 g) and 30% H2O2(0.28 mL) were added into the solution at 0 C stirring for1.5 h at 25 C. Water (1 mL) and NaHCO3 (0.132 g)were added into the 3,6-difluoropyrazine-2-carboxamidewith magnetic stirring for 8 h at 50 C and TLC (MeOH:EA = 1:1, v/v, Rf = 0.72) was used to monitor thereaction. Then, 6 M HCl was added into the solution andthe pH of the solution was adjusted to 1.0. Then, thesolution was extracted with ethyl acetate (5 9 10 mL).The organic phase was washed with brine (3 9 10 mL),dried with anhydrous Na2SO4, and was filtered to removethe drying agent. The ethyl acetate was removed by distillationunder reduced pressure to obtain the crudecompound of 7. Then, the crude 7 was dissolved intoEtOH (6 mL, 95%). The suspension was heated to refluxfor 30 min and was filtered to crystallize. The filtrate wascooled to 25-30 C which was kept for 4 h. The crystal ofpure 6-fluoro-3-hyroxypyrazine-2-carboxamide (7)(0.25 g, 60%) was obtained in open system.

The synthetic route of 356783-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Feng-Liang; Li, Cui-Qin; Xiang, Hao-Yue; Feng, Si; Chemical Papers; vol. 71; 11; (2017); p. 2153 – 2158;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 74290-67-8,Some common heterocyclic compound, 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, molecular formula is C5H6BrN3, 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 2-amino-5-bromo-3-methylpyrazine (46.5 g, 247.3 mmol) in acetonitrile (450 mL) and THF (750 mL) was added DMAP (3 g, 24.7 mmol). The reaction mixture was stirred for 15 minutes before the addition of di-tert-butyl dicarbonate (242 g, 1 112.8 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated in vacuo, then diluted with EtOAc (750 mL) and washed with water (500 mL). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The black tar was purified via flash chromatography, using a 10-15% EtOAc in heptane gradient. The resultant solid was triturated with IP A. The resulting white solid (the bis-tert-butoxycarbonyl derivative) was dissolved in methanol (3000 mL), then K2CO3 (61.25 g, 443 mmol) was added. The reaction mixture was stirred overnight at room temperature, then at 60C for 1 h, then allowed to cool and concentrated in vacuo. The residue was dissolved in DCM (1000 mL), then washed with water (2 x 1000 mL) and brine (500 mL). The organic layers were dried over magnesium sulphate, then concentrated in vacuo, to give the title compound (38 g, 80% pure by LCMS). LCMS (ES+) [M+H]+ 288.1 and 289.1 , RT 1.42 minutes (method 1).

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

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; HORSLEY, Helen Tracey; HUANG, Qiuya; REUBERSON, James Thomas; VANDERHOYDONCK, Bart; WO2014/96423; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem