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. 19847-12-2, name is Pyrazinecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Pyrazinecarbonitrile

To a solution of pyrazine-2-carbonitrile (1.0 g, 9.52 mmol) in methanol (20 mL) was addedNaOCH3 (0.10 g, 1.90 mmol). The resulting mixture was heated with stirring at rt for 12 hrs. Tothe reaction mixture was added NH4C1 (0.51 g, 9.52 mmol). After being heated under reflux for 3 hrs, the resulting reaction mixture was concentrated in vacuo. The residue was suspended in ethanol (30 mL). The suspension was heated under reflux for 1 hr, then cooled to rt and filtered. The filtrate was concentrated in vacuo to give pyrazine-2-carboxamidine hydrochloride (1.2 g),which was used in the next step without further purification.

According to the analysis of related databases, 19847-12-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, 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. Computed Properties of C4H3ClN2

In a sealed tube, 2-chloropyrazine (1.0 g, 8.7 mmol, 1 equiv) was heated withethanolic methylamine (33% w/w; 4.0 g, 43.6 mmol, 5 equiv) at 95 C for 1 h.Solvent and excess of methylamine were then removed under reduced pressure. Theresidue was then dissolved in dichloromethane and washed three times with water.The organic phase was then evaporated under reduced pressure and the crude productwas further purified by flash chromatography on silica gel (EtOAc/Et2O= 1:6 to 1:4).The product S2 was obtained as a colorless oil (0.73 g, 6.7 mmol, 77% yield), whichsolidified as a light brown solid. The spectra are in agreement with the literaturereport.1

The synthetic route of 2-Chloropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Qi; Qin, Ling; Zard, Samir Z.; Tetrahedron; vol. 74; 40; (2018); p. 5804 – 5817;,
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 5521-58-4 as follows. Recommanded Product: 5-Methylpyrazin-2-amine

Oxalyl chloride (1.9 mL, 22.2 mmol) and DMF (1 drop) were added to a solution of 3- [(phenylmethyl)oxy]-5-[(3^-tetrahydrofuran-3-yloxy]benzoic acid (5.8 g, 18.5 mmol) in DCM (100 mL) and the mixture stirred at RT for 16 hours. The mixture was evaporated in vacuo to a residue which was redissolved in DCM (25 mL) and added to a stirred mixture of 2-amino-5-methylpyrazine (2.22 g, 20.35 mmol) and pyridine (1.81 mL, 22.2 mmol) in DCM (100 mL) at 50C – 1O0C. The mixture was stirred at RT for 18 hours, the DCM evaporated in vacuo to give a residue which was partitioned between water (50 mL) and ethyl acetate (125 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 60% ethyl acetate in isohexane, to give the desired material (5.1 g). 1H NMR delta (CDCl3): 2.1 – 2.2 (m, 2H), 2.5 (s, 3H), 3.8 – 3.95 (m, 4H), 4.9 (m, IH), 5.0 (s, 2H), 6.6 (s, IH), 6.95 (s, IH), 7.05 (s, IH), 7.35 (m, 5H), 8.05 (s, IH), 8.3 (s, IH), 9.5 (s, IH); m/z 406 (M+H)+.

According to the analysis of related databases, 5521-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125972; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, 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: 33332-25-1

A mixture of 4-aminotetrahydropyran (500 mg, 4.94 mmol) and methyl 2-chloropyrazine-5-carboxylate (770 mg, 4.46 mmol) in DMF (5 mL) containing N,N-diisopropylethylamine (1.0 mL, 5.7 mmol) was stirred at 55 C. for 17 hrs. The reaction mixture was concentrated and the residue was partitioned between ether (25 mL) and hydrochloric acid (1N, 25 mL). The aqueous layer was further extracted with ether (25 mL). The resulting aqueous layer was first treated with sodium chloride (10 g) and then extracted with methylene chloride (3¡Á50 mL). The organic layer was washed with brine and dried over sodium sulfate. Solvents were evaporated to give an oil which slowly crystallized as methyl 2-(N-tetrahydropyran-4-yl)-aminopyrazine-5-carboxylate (900 mg, 85%). MS calcd for C11H15N3O3 (m/e) 237, obsd 238.1 (M+H).

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolin, David Robert; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Hamilton, Matthew Michael; Li, Shiming; McDermott, Lee Apostle; Qian, Yimin; Yun, Weiya; US2007/123504; (2007); 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. 121246-96-6, name is 3-Chloropyrazine-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Chloropyrazine-2-carbaldehyde

PREPARATION 14; EPO 4-Methyl-3,4,5,6-tetrahvdro-2H-?,2’lbipyrazinyl-3′-carbaldehvde;.S-Chloro-pyrazine^-carb-aldehyde (Turck, et al., Synthesis 1988, 881-4) (6.01 g, -40 mmol), N-methylpiperazine (6.6 mL, 59.4 mmol) and K2CO3 (8.3g, 60.0 mmol) were refluxed for 1h in dioxane (250 mL). After cooling, the mixture was filtered and concentrated to an orange oil. This was dissolved in EtOAc (500 mL) and washed with water (4×150 mL) and brine, dried (MgSO4) and concentrated. Chromatography with 5% MeOH/ CH2CI2 gave 3.34 g (40%) of PP14 as a dark red oil : NMR (CDCI3) 9.94 (s, 1 H), 8.18 (d, J= 2.1 Hz, 1 H), 8.08 (d, J = 2.1 Hz, 1 H), 3.59 (t, J= 5.2 Hz, 4H), 2.53 (t, J = 5.0 Hz, 4H), 2.32 (s, 3H).

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 121246-96-6.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2006/48727; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

N,N-Dimethylformamide (2 mL), triethylamine (0.081 mL, 0.58 mmol) and 1- [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (48 mg, 0.126 mmol, HATU) were added to a mixture of the product of Example 197B (40 mg, 0.097 mmol) and 5-(difluoromethyl)pyrazine-2-carboxylic acid (Manchester, 16.9 mg, 0.097 mmol) in sequential order. The reaction mixture was then stirred at ambient temperature for 0.5 hour. The resulting solution was filtered through a glass microfiber frit and purified by preparative HPLC [Waters XBridge C185 mum OBD column, 30 ¡Á 100 mm, flow rate 40 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (39 mg, 0.086 mmol, 88% yield). 1H NMR (500 MHz, DMSO-d6) delta ppm 9.34 (s, 1H), 9.31- 9.22 (m, 1H), 8.99 (s, 1H), 8.53 (s, 1H), 7.50 (t, J = 8.9 Hz, 1H), 7.21 (t, J = 54.0 Hz, 1H), 7.08 (dd, J = 11.4, 2.8 Hz, 1H), 6.86 (ddd, J = 9.0, 3.0, 1.1 Hz, 1H), 4.49 (s, 2H), 2.18 – 2.12 (m, 2H), 1.99- 1.80 (m, 6H); MS (ESI+) m/z 455 (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, 5-(Difluoromethyl)pyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (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. 681249-57-0, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine

To a slurry of (3-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (200 mg, 0.451 mmol)) and 2-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (95 mg, 0.496 mmol) in dry MeCN (5 mL, 96 mmol), was added DIEA (0.197 mL, 1.128 mmol) and the resulting white suspension was stirred at room temperature for 2 h and heat to 40 C. for 4 additional hours The mixture was cooled at 0 C. The suspension was filtered. The solid was washed with water (~50 mL) and dried in vacuum oven at 50 C. to give 3-(1-oxo-4-((4-((2-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)methyl)benzyl)oxy)isoindolin-2-yl)piperidine-2,6-dione as a white solid (135 mg, 54% yield): HPLC: Waters Symmetry C18, 5 mum, 3.9*150 mm, 1 ml/min, 240 nm, 40/60 CH3CN/0.1% H3PO4, 6.33 min (98.2%); mp: 139-142 C.; 1H NMR (DMSO-d6) delta 1.89-2.05 (m, 1H, CHH), 2.34-2.48 (m, 1H, CHH), 2.57 (d, J=19.1 Hz, 1H, CHH), 2.82-2.98 (m, 1H, CHH), 3.02 (t, J=5.5 Hz, 2H, CH2), 3.80 (s, 2H, CH2), 3.82 (s, 2H, CH2), 4.20-4.31 (m, 3H, CHH, CH2), 4.42 (d, J=17.6 Hz, 1H, CHH), 5.11 (dd, J=5.1, 13.2 Hz, 1H, CH), 5.25 (s, 2H, CH2), 7.30-7.36 (m, 2H, Ar), 7.38-7.44 (m, 2H, Ar), 7.45-7.54 (m, 3H, Ar), 10.96 (s, 1H, NH); 13C NMR (DMSO-d6) delta 22.34, 31.16, 45.07, 46.54, 47.73, 49.17, 51.56, 59.42, 69.35, 114.99, 115.23, 127.80, 128.92, 129.80, 129.95, 133.30, 135.73, 137.05, 152.82, 153.46, 167.97, 170.95, 172.80; Two carbon signals are not observed (probably due to splitting of CF3, and CCF3); LCMS: MH=555; Anal Calcd for C27H25F3N6O4+0.5 H2O: C, 57.55; H, 4.65; N, 14.91; F, 10.11; Found: C, 57.42; H, 4.32; N, 14.60; F, 9.92.

According to the analysis of related databases, 681249-57-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 54013-04-6, name is Ethyl 5-chloropyrazine-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 54013-04-6, category: Pyrazines

Ethyl 5-chloro-2-pyrazinecarboxylate (1.74 mmol) was added hydrazine monohydrate (1 mL) and heated 100 C for1 h. Then ethanol was added (10 mL), the mixture was refluxed for 3 h, finally filtered and washed with ethanol[19]. Brown crystals from ethanol. lambda max. (EtOH) (nm) (logepsilon): 203 (4.69), 279 (5.21), 327 (4.79); IR max.(cm-1): 3327,3277, 3100, 1627, 1568, 1537, 1496, 1197, 1116, 889, 696; 1H-NMR (300 MHz), (DMSO-d6/TMS) ppm: 4.42 (d, 2H,NH2), 8.45 (s, 1H, pyrazine H6 ), 8.61 (s, 1H, pyrazine H3),9.41 (s, 1H, NH). Anal. Cal. for C5H5ClN4O (M.W.: 172.572g/mol): C, 34.80; H, 2.92; N, 32.47. Found: C, 34.60; H,2.90; N, 32.00

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, Ethyl 5-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kocyigit-Kaymakcioglu, Bedia; Yazici, Senem Sinem; Tok, Fatih; Dikmen, Miri?; Enguer, Selin; Oruc-Emre, Emine Elcin; Iyidogan, Aysegul; Letters in drug design and discovery; vol. 16; 5; (2019); p. 522 – 532;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4774-14-5,Some common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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 B-10: Preparation of (2S)-1-(4-(1-isopropyl-3-(5-methyl-5H-pyrrolo[3,2-b]pyrazin-2-yl)-1H- pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-10) cr Et3NB-10-1 B-10-2 B-10-3Preparation of 6-chloropyrazin-2-amine (B-10-2). B-10-1 B-10-2A mixture of 2,6-dichloropyrazine (300 g, 2 mol) and 28% aq. NH3 (8 L) was stirred at 14O0C in a sealed system for 14 hours. TLC (petroleum ether/EtOAc 3:1 ) indicated complete consumption of starting material. The reaction mixture was extracted with EtOAc (3 L x 3). The combined organic layers were washed with saturated aqueous NaCI (3 L), dried over Na2SO4 and concentrated in vacuo to give crude compound B-10-2, which was purified by column chromatography (silica gel, petroleum ether/EtOAc 2:1) to yield pure compound B-10-2 (410 g, yield: 59.7%) as a white solid.

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 113305-94-5, 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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

5-chloro-3- (cyclohex-1-en-1-yl) -7-methoxy-6- (4-methoxyphenyl) -2-phenylpyrazolo [1, 5-a] pyrimidine (500 mg, 1.07 mmol) , 5-aminopyrazine-2-carbonitrile (257 mg, 2.15 mmol) , palladium (II) acetate (48 mg, 0.214 mmol) , xantphos (124 mg, 0.214 mmol) and sodium carbonate (230 mg, 0.215 mmol) in 1, 4-dioxane (10 mL) under heating at 110 for 4 hours under nitrogen atmosphere. LC-MS: m/z 530.2 (M+H) +.

The synthetic route of 5-Aminopyrazine-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; TRAVINS, Jeremy, M.; KONTEATIS, Zenon, D.; SUI, Zhihua; YE, Zhixiong; (199 pag.)WO2018/39972; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem