Tag: M.W=100-200

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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

Step 1: Synthesis of Intermediate 1-4.1R8 (212 g, 1151 mmol) in tetrahydrofuran (dry) (600 mL) is cooled to -78°C. Then n-butyllithium(2.5 M in hexanes, 552 mL, 1381 mmol) is added dropwise, keeping the temperature below -78°C.After 30 mm R9 (324g, 1209 mmol) in tertahydrofuran (dry) (120 mL) is added dropwise. Thereaction mixture is stirred at -78°C for 1 h. The mixture is quenched with saturated NH4C1 solutionand extracted three times with ethyl acetate. The organic layer is washed with brine, dried overNa2SO4 and evaporated in vacuo. The residue is purified by flash chromatography (heptane/ ethyl acetate = 80/20). Yield 60percent.

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 109838-85-9.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140091; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

14508-49-7, name is 2-Chloropyrazine, 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. Recommanded Product: 14508-49-7

A mixture of CHLOROPYRAZINE (9.6 g, 83.3 MMOL) and hydrogen peroxide solution (30%, 16 mi) in glacial acetic acid (26 ml) was heated at 70 C for 18 hours. The mixture was allowed to cool to room temperature, poured into water (250 ml) and extracted with DICHLOROMETHANE (3 x 100 ML). The DICHLOROMETHANE extracts were combined, washed with saturated sodium bicarbonate solution (2 x 70 ML), water (3 x 100 ML) and brine (100 ml). The organic portion was dried under sodium sulfate and evaporated in vacuo to give a white solid which was recrystallised from absolute ethanol to give the title compound (0.45 g). ‘H NMR (CDCI3) 8.27-8. 26 (1H, d), 8.15 (1 H, S), 8.03-8. 02 (1 H, dd).

The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/56369; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 74290-67-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 74290-67-8 name is 2-Amino-5-bromo-3-methylpyrazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

a) 3-(N-(3-((5-amino-6-methylpyrazin-2-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)-5-chloro-2-methoxybenzyl Acetate A mixture of 5-chloro-3-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)-2-methoxybenzyl acetate (200 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (34.3 mg), DIPEA (2 mL), copper(I) iodide (17.7 mg), 5-bromo-3-methylpyrazin-2-amine (114 mg) and DMSO (2 mL) was stirred under microwave irradiation at 100 C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (216 mg). MS: [M+H]+ 537.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-5-bromo-3-methylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); 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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. 6863-74-7

A mixture of tert-butyl ((1R,4R,7R)-2-(1-(azetidin-3-ylmethyl)-2-(1- (cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1H-benzo[d]imidazole- 5-carbonyl)-2-azabicyclo[2.2.1]heptan-7-yl)carbamate (15 mg, 0.024 mmol), 6- chloropyrazine-2-carbonitrile (3.34 mg, 0.024 mmol), cesium carbonate (15.62 mg, 0.048 mmol), BINAP (0.746 mg, 1.199 mmol) and Pd2(dba)3 (1.098 mg, 1.199 mmol) in degassed dioxane (1.0 mL) under nitrogen in a seal vial was stirred at 90C for 18 hour. The mixture was diluted with EtOAc (5 mL) and was washed with a solution of aqueous saturated sodium bicarbonate (5 mL). The organic layer was dried over sodium sulfate and concentrated to give crude tert-butyl ((1R,4R,7R)-2-(1-(azetidin-3-ylmethyl)-2-(1- (cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1H-benzo[d]imidazole- 5-carbonyl)-2-azabicyclo[2.2.1]heptan-7-yl)carbamate (15 mg, 0.024 mmol). Material was used as is in next reaction.

The synthetic route of 6863-74-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NGU, Khehyong; (435 pag.)WO2020/33514; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 768-05-8, A common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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 dried RB flask, KOH (1.42 g, 25.33 mmol) was suspended in ethanol (50 mL) atambient temperature. Then pyrazine-2-carbohydrazide6a (5 g, 36.19 mmol) was added and reaction mass was cooled.Carbon disulfide (2.4 mL, 39.81 mmol)was added dropwise and the resulting mixture was refluxed for 12 h. Thereaction progress was monitored by TLC and after completion of the reactionsolvent was distilled under vacuum. The reaction pH was adjusted to 6.0-7.0 by adding4N HCl. The precipitated solid was collected by filtration, washed with water(50 mL) and dried to give white solid compound 7a. Yield: 5.71 g, 87 %; 1HNMR (CDCl3, 400 MHz, delta inppm): 14.817 (s, 1H, -SH), 9.193 (bs, 1H, Ar-H), 8.793 (s, 1H, Ar-H), 8.764 (s,1H, Ar-H); 13C NMR (100 MHz, CDCl3) delta (ppm): 168.7, 164.2, 152.6, 147.7, 145.4, 143.5; ESI-MS (m/z)= 181.1 (M+H)+; calculated for C6H4N4OS;C, 39.99; H, 2.24; N, 31.09; S, 17.80. Found: C, 39.97; H, 2.25; N, 31.05; S,17.84.

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; Reddyrajula, Rajkumar; Dalimba, Udayakumar; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 939412-86-9, These common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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.

2- (5-chloro-2-ethoxy-4-methyl-3- (6-methylpyridin-3-yl) phenyl) propanoic acid (2.7 g, 8.09 mmol) , (3-chloropyrazin-2-yl) methanamine hydrochloride (1.4 g, 9.71 mmol) , HOBt (1.32 g, 24.27 mmol) , EDCI (1.86 g, 9.71 mmol) and DIPEA (3.14 g, 24.27 mmol) were dissolved in THF (30 mL) and stirred at room temperature under N 2 for overnight, brine (20 mL) was added and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over Na 2SO 4. The product (3.2 g in 86.1 %yield) was got. MS (ESI) m/e (M+1) +459.

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIGENE, LTD.; LI, Jing; ZHAO, Haibo; WANG, Zhiwei; (193 pag.)WO2018/103688; (2018); 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 5521-61-9 as follows. SDS of cas: 5521-61-9

INTERMEDIATE 71 PREPARATION OF (6-METHYLPYRAZIN-2-YL)METHANOL To a solution of 6-methylpyrazine-2-carboxylic acid (8.00 g, 58.0 mmol) in N,N- dimethylformamide (50 mL) were added Cs2CO3 (37.8 g, 116 mmol) and iodomethane (12.3 g, 87.0 mmol). After being stirred overnight at room temperature, the reaction mixture was quenched with water (100 mL) and extracted with EtOAc (5 x 150 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was then diluted with water (50 mL). NaBH4 (12.5 g, 330 mmol) was added portionwise at 0 C. After addition, the resulting mixture was stirred at room temperature for 30 min, cooled to 0 C, diluted with water (150 mL) and extracted with EtOAc (8 x 100 mL). The combined organic layers were washed with brine (200 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (2.9 g, crude) as a yellow solid.1H NMR (400 MHz, DMSO-d6) delta 8.50 (s, 1H), 8.42 (s, 1H), 5.55 (t, J = 5.8 Hz, 1H), 4.59 (d, J = 5.5 Hz, 2H), 2.47 (s, 3H).

According to the analysis of related databases, 5521-61-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DENALI THERAPEUTICS INC.; BONANOMI, Giorgio; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; LESLIE, Colin Philip; LYSSIKATOS, Joseph P.; NAPOLITANO, Carmela; POZZAN, Alfonso; SUDHAKAR, Anantha; SWEENEY, Zachary K.; TONELLI, Federica; DE VICENTE FIDALGO, Javier; (232 pag.)WO2017/96301; (2017); 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., name: (3-Chloropyrazin-2-yl)methanamine hydrochloride

(c) (6R,8aS)-N-((3-chloropyrazin-2-yl)methyl)-3-oxo-1-vinylhexahydro-1H-oxazolo[3,4-a]pyridine-6-carboxamide To a solution of (6R,8aS)-3-oxo-1-vinylhexahydro-1H-oxazolo[3,4-a]pyridine-6-carboxylic acid (60 mg, 0.28 mmol) in DCM (5 mL) was added (COCl)2 (54.1 mg, 0.43 mmol) at 0 C. and stirred at 20 C. for 1 h under N2 atmosphere. The mixture was concentrated in vacuo to give the residue, which was dissolved in THF (2 mL) and followed by (3-chloropyrazin-2-yl)methanamine hydrochloride (76.7 mg, 0.43 mmol) and Et3N (86.2 mg, 0.85 mmol). The mixture was stirred at 20 C. for 5 h. TLC (PE: THF=1:1) showed the starting materials was consumed completely. Then the reaction mixture was poured into water (10 mL), extracted with EA (10 mL*2). The organic layer was concentrated in vacuo and purified with pre-TLC to afford (6R,8aS)-N-((3-chloropyrazin-2-yl)methyl)-3-oxo-1-vinylhexahydro-1H-oxazolo[3,4-a]pyridine-6-carboxamide (30 mg, yield 31.4%) as a white solid. 1HNMR (400 MHz, Methanol-d4): delta=8.53 (dd, J=1.0, 2.5 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 6.04-5.88 (m, 1H), 5.50-5.31 (m, 2H), 4.65-4.57 (m, 3H), 3.98-3.89 (m, 1H), 3.83 (ddd, J=3.4, 8.2, 11.8 Hz, 1H), 3.50-3.42 (m, 1H), 2.58-2.42 (m, 1H), 2.10 (dd, J=2.5, 12.8 Hz, 1H), 2.03-1.95 (m, 1H), 1.77-1.63 (m, 2H), 1.53-1.38 (m, 111).

According to the analysis of related databases, 939412-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (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. 14508-49-7, name is 2-Chloropyrazine, A new synthetic method of this compound is introduced below., Formula: C4H3ClN2

2-Chloropyrazine (7.79 mL, 87 mmol, commercially available e.g. from Sigma- Aldrich or Haiso PharmChem) was dissolved in ethanol (50 mL), and hydrazine hydrate (6.85 mL, 218 mmol) was added. The solution was refluxed for 6 hours. The mixture was cooled to room temperature and the solvent was partially evaporated. The residue was diluted with water and extracted with 10% (v/v) of 2-propanol/Dichloromethane solution (5 extractions). The combined organic phases were then dried and evaporated to give a yellow solid which was triturated with diethyl ether to give 2-hydrazinopyrazine as a yellow solid (3.32 g).

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; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 54608-52-5, These common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, 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 2-hydrazinopyrazine (1.10 g) in trifluoroacetic anhydride (10 mL) was stirred at room temperature for 4 h. To the mixture was added PPA (12 mL). The reaction mixture was heated at 80 C for another 15 h. The reaction mixture was cooled to room temperature and filtered to afford the title compound as a white solid (0.94 g, 50.00 %). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 189.0 (M+l); ? NMR (400 MHz, CDC13) ?: 8.64 (s, 3H).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Jiancun; ZHANG, Yingjun; ZHANG, Weihong; LIU, Bing; ZHANG, Jiquan; LIU, Jinlei; ZHANG, Lu; WO2013/71697; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem