Month: June 2021

Some common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H15BrN4O2, 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. Product Details of 723286-80-4

3-Bromo-5,6-dihydro-8H-[l,2,4]triazolo[4,3-a]pyrazine-7-carboxylic acid tert- butyl ester (54.8 mg, 0.181 mmol), 4-(( ^)-3-mo holin-4-yl-l-phenylsulfanyl-methyl- propylamino)-3-trifluoromethanesulfonyl-benzenesulfonamide ( 100 mg, 0.181 mmol), (IS, 25)-N,N’-dimethyl-cyclohexane-l,2-diamine (07.71 mg, 0.054 mmol), cesium carbonate (100 mg, 0.307 mmol), and copper (I) iodide (5.16 mg, 0.027 mmol) were added to a microwave vial followed by toluene (2 mL). The reaction mixture was degassed for 15 minutes under nitrogen and then heated to 90C for 14 hours. The crude material was directly purified via flash chromatography on silica gel (0-25% 7 N ammonia in methanol in CH2C12) to afford the title compound (130 mg, 92% yield). MS [m/z; (M+l)+]: 776.5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 723286-80-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; MILLER-MOSLIN, Karen; TOURE, Bakary-Barry; VISSER, Michael Scott; YUSUFF, Naeem; WO2011/29842; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 25911-65-3,Some common heterocyclic compound, 25911-65-3, name is 3-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

c) 4-Amino-2-(ethoxymethyl)pteridine A mixture of 36.0 g (0.30 mole) of 3-amino-2-pyrazinecarbonitrile [prepared according to A. Albert and K. Ohta, J. Chem. Soc. C, 1970, 1540] and 46.7 g of 2-ethoxyacetamidine in 700 ml of absolute control is refluxed for 2 hours 30 minutes under a nitrogen atmosphere. After cooling, the precipitate obtained is isolated by filtration. It is purified by recrystallization from ethanol. Yld: 52.0 g (84%), m.p. 152-154 C. NMR (DMSO-d6): delta=1.1 (3H, t); 3.5 (2H, q); 4.4 (2H, s); 8.2 (2H, peak exchangeable with CF3 COOD); 8.7 (1H, d); 9.0 (1H, d).

The synthetic route of 25911-65-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lipha, Lyonnaise Industrielle Pharmaceutique; US5167949; (1992); 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 33332-25-1 as follows. Quality Control of Methyl 5-chloropyrazine-2-carboxylate

Example 7[0142] [Formula 41] [0143]1) In tetrahydrofuran (75 mL) was dissolved methyl 5-chloropyrazin-2-carboxylate (2.589 g), 1M diisobutyl aluminum hydride-tetrahydrofuran solution (30 mL) was added dropwise to the solution at 0C, and the mixture was stirred at the same temperature for 15 minutes. To the mixture were added water and IN hydrochloric acid, then, a saturated aqueous sodium bicarbonate solution was added to the same to make the pH to 7. The mixture was filtered through Celite, and then, extracted with chloroform 3 times. The organic layer was separated, dried over anhydrous sodium sulfate, and the residue obtained by concentrating the same under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate=90: 10 to 65:35 to 50:50) to obtain (5-chloropyrazin-2-yl)methanol (465 mg). MS (m/z): 147/145 [M+H]+

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SAKURAI, Osamu; SARUTA, Kunio; HAYASHI, Norimitsu; GOI, Takashi; MOROKUMA, Kenji; TSUJISHIMA, Hidekazu; SAWAMOTO, Hiroaki; SHITAMA, Hiroaki; IMASHIRO, Ritsuo; WO2012/81736; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 2727-13-1, A common heterocyclic compound, 2727-13-1, name is 3-Amino-6-chloropyrazine-2-carboxylic acid, molecular formula is C5H4ClN3O2, 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 mixture of 3-amino-6-chloro-pyrazine-2-carbox-ylic acid (26.0 mg; 0.150 mmol), the amine intermediateIX.3 (100 mg; 0.151 mmol), TETU (53.0 mg; 0.165 mmol),triethylamine (63.2 jtl; 0.450 mmol) and DMF (5.0 ml) isstirred at tt. overnight. Volatiles are evaporated and theresidue is purified by RP-HPLC (Cl 8; water-ACN-TFA).10130] C25H33C1N7O5SxC2O2F3 ESI Mass spectrum_mlz=590 [M+H]+10131] HPLC analytics: RT=0.42 mm (HPLC method D)

The synthetic route of 2727-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; HECKEL, Armin; HAMPRECHT, Dieter; KLEY, Joerg; WIEDENMAYER, Dieter; (29 pag.)US2017/50992; (2017); 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Safety of 3-Amino-6-bromopyrazine-2-carboxylic acid

Step 1 : 3-amino-6-bromo-Lambda/”-(phenylcarbonyl)pyrazine-2-carbohydrazide[00397] TBTU (22.09 g, 68.80 mmol) and Et3N (4.642 g, 6.394 mL, 45.87 mmol) were added to a solution of 3-amino-6-bromo-pyrazine-2-carboxylic acid (10 g, 45.87 mmol) and benzohydrazide (7.494 g, 55.04 mmol) in DMF (100.0 mL) and the resulting solution stirred at ambient temperature overnight. The reaction mixture was poured into water and the resultant precipitate was filtered and dried under vacuum. This was triturated with hot EtOAc and the resulting precipitate filtered and dried to give the desired product (13.11 g, 85% Yield). IH NMR (400.0 MHz, DMSO) d 7.53 (t, 2H), 7.60 (d, IH), 7.69 (br s, 2H), 7.91 (d, 2H), 8.44 (s, IH), 10.48 (s, IH) and 10.55 (s, IH) ppm; MS (ES+) 338.92

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 54608-52-5, 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. 54608-52-5, name is 2-Hydrazinopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

1) 5-(5-Methyl-2-pyridyl)-1-(2-pyrazinyl)-1H-pyrazole-3-carboxylic acid ethyl ester 2-Hydrazinopyrazine (2.363 g) obtained in Referential Example 2 and a solution of 4-(5-methyl-2-pyridyl)-2,4-dioxobutanoic acid ethyl ester (5.04 g) obtained in Method A-step 2) of Referential Example 9 in ethanol (100 mL) were refluxed for 2 hours, followed by cooling in air. To the reaction mixture, concentrated hydrochloric acid (2.65 mL) was added, and the mixture was refluxed for 1 hour, followed by cooling in air. The reaction mixture was neutralized with 1N aqueous sodium hydroxide and then extracted with chloroform. Further, the aqueous layer was extracted with chloroform, and the organic layers were combined, followed by washing with saturated brine and drying over sodium sulfate anhydrate. After a filtration step, the solvent was evaporated under reduced pressure, and the residue was purified through silica gel column chromatography (acetone – chloroform), to thereby give 5-(5-methyl-2-pyridyl)-1-(2-pyrazinyl)-1H-pyrazole-3-carboxylic acid ethyl ester as an amorphous product (1.336 g, 22%). 1H-NMR(400MHz,CDCl3)delta:1.43(3H,t,J=6.9Hz), 2.34(3H,s), 4.47(2H,q,J=6.9Hz), 7.23(1H,s), 7.24-7. 30 (1H,m), 7.46(1H,d,J=7.9Hz), 7.56(1H,dd,J=7.9,1.5Hz), 8.21(1H,br s), 8.28-8.32(1H,m), 8.56(1H,d,J=2.4Hz), 9.02(1H,d like, J=1.5Hz). FAB-MS m/z:310(M+H)+.

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

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1762568; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4744-50-7,Some common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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: Pyrazine-2,3-dicarboxylic anhydride (1.0 g, 6.7 mmol) was dissolved in tetrahydrofuran (40 mL)in an Erlenmeyer flask and the corresponding substituted aniline (6.7 mmol, 1 equiv.) was added in one dose. The reaction mixture was stirred for 1 hour at laboratory temperature. Water (30 mL) was added into the mixture followed by the saturated aqueous solution of NaHCO3 until pH 6 to form thecorresponding 3-(phenylcarbamoyl)pyrazine-2-carboxylic acid 1-18. Obtained crystals were filtered off and washed with water. The progress of the procedure was monitored by TLC eluted with thesystem water/butanol/acetic acid 5:4:1.

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

Reference:
Article; Semelkova, Lucia; Jano?cova, Petra; Fernandes, Carlos; Bouz, Ghada; Jand?Ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; Molecules; vol. 22; 9; (2017);,
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. 57948-41-1, name is 3-Bromoimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C6H4BrN3

A mixture of 3-bromoimidazo[1,2-alpha]pyrazine (150 mg, 0.76 mmol), potassium phosphate (321 mg, 1.51 mmol) and 3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (3 ml of a 0.5M solution in N,N-dimethylacetamide) were degassed with N2 for 15 min. Tetrakis(triphenylphosphine)palladium(0) (44 mg, 0.04 mmol) was added and the mixture heated at 80 C. for 18 h. The reaction was allowed to cool to room temperature, diluted with water (20 ml) and saturated sodium hydrogencarbonate solution (20 ml) then extracted with ethyl acetate (2*75 ml). The combined organic fractions were washed with brine (40 ml), dried over anhydrous sodium sulfate and evaporated to give a black oil. The oil was purified by silica gel chromatography eluding with dichloromethane and 1% 0.88 ammonia on a gradient of methanol (1-2%). The solid obtained was triturated with diethyl ether which gave 3′- (imidazo[1,2-alpha]pyrazin-3-yl)biphenyl-2-carbonitrile (83 mg, 37%) as a white powder: deltaH (400 MHz, CDCl3) 7.52 (1H, td, J 8 and 1), 7.58 (1H, dd, J 8 and 1), 7.61-7.74 (4H, m), 7.80-7.85 (2H, m), 7.94-7.97 (2H, m), 8.55 (1H, d), 9.18 (1H, s).

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; Goodacre, Simon Charles; Hallett, David James; Street, Leslie Joseph; US2004/19057; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 23688-89-3, 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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of Compound 3A (220 mg, 1.39 mmol; prepared as described in Sato, N. J. Heterocyc. Chem. 1994,31, 1177), DPPA (575 mg, 2.09 mmol) and triethylamine (0. [39] [ML,] 2. 80 mmol) in [T-BUOH] (3 mL) and toluene (2 mL) was heated at [65 C] for 1.5 h, then at [85 C] for 2 h. After concentration, the mixture was purified by flash chromatography (EtOAc/hexane) to give Compound 3B (180 mg, 57%) as a white [SOLID. 1H NMR] (300 MHz, CDC13) 8 [9. 19 (S,] 1H), 8.26 (s, 1H), 7.17 (brs, 1H), 1.54 (s, 9H). A mixture of Compound 3B (160 mg, 0.697 mmol), [(3-BROMOPROPOXY)-TERT-] butyldimethylsilane (220 mg, 0.870 mmol) and [CS2CO3] (340 mg, 1.04 mmol) in dry DMF (2 mL) was stirred at [60 C] for 2.5 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (EtOAc/hexane) to provide Compound 3C (262 mg, 94%) as clear [OIL. LH NMR (300 MHZ, CDC13) 6 9.] 01 (s, 1H), 8.20 (s, 1H), 4.00 (t, J= 7.4 Hz, 2H), 3. 68 (t, J= [6.] 2 Hz, 2H), 1.87 [(M,] 2H), 1.54 (s, 9H), 0.87 (s, 9H), 0.03 (s, 6H). A mixture of Compound 3C (123 mg, 0.306 mmol), bis [(TRIMETHYLTIN)] (200 mg, 0.611 mmol), tetrakis (triphenylphosphine) palladium (35 mg, 0.030 mmol), LiCl (40 mg, 0.94 mmol) and 2, 6-di-tert-butyl-4-methylphenol (3 mg, 0.014 mmol) in anhydrous 1,4- dioxane (2 [ML)] was refluxed for 4 h under nitrogen. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel (EtOAc/hexane) to give Compound 3D (154 mg, 95%) as clear [OIL. 1H NMR] (300 MHz, CDC13) 8 8.79 (s, 1H), 8.21 (s, [1H),] 4.01 (t, J= 7.2 Hz, 2H), 3.67 (t, J= 6.0 Hz, 2H), 1.90 [(M,] 2H), 1.53 (s, 9H), 0. 87 (s, 9H), 0.36 (s, 9H), 0.02 (s, 6H); MS (ES) m/z : 531 (M+H). A mixture of Compound 3D (73 mg, 0.14 [MMOL),] Compound 1C (52 mg, 0.15 mmol), dichlorobis (triphenylphosphine) palladium (15 mg, 0.021 mmol) and LiCl (18 mg, 0.42 mmol) in anhydrous toluene (3 mL) was stirred at [100 C] overnight under nitrogen. The mixture was cooled, concentrated under vacuum and purified by flash chromatography (EtOAc/hexane) to give the coupled product as yellow oil. TFA (1 mL) was added and the mixture was stirred at [20 C] for 4 h. After it was concentrated, saturated NH40H solution and water were added until the mixture turned basic. After the precipitated solid was collected through filtration, it was washed with water and [ET20] and dried under vacuum to provide Compound 3 (1.5 mg, 47%) as a yellow solid. [H NMR] (300 MHz, DMSO-d6) [6] 10.59 (s, 1H), 8.91 (s, 1H), 8.63 (s, 1H), 8.20 (brs, 1H), 8.12 (s, 1H), 7.80 (brs, 1H), 7.39 (t, J= 8.2 Hz, 1H), 7.34 (brs, 1H), 7.13 [(D,] [J=] 7.8 Hz, 1H), 4.60 [(M,] 1H), 3.50 [(M,] 2H), 3.32 [(M,] 2H), 1.76 (t, J= 6.4 Hz, [2H) ;] MS (ES) m/z: 358 [(M+H.]

The synthetic route of 6-Chloropyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; KUO, Gee-Hong; DEANGELIS, Alan; WANG, Aihua; ZHANG, Yan; EMANUEL, Stuart, L.; MIDDLETON, Steve, A.; WO2004/9562; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 21279-64-1, 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. 21279-64-1, name is 5-Chloropyrazine-2-carboxamide belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 150 mg (0.952 mmol) of 5-Cl-PZA (1) or 6-Cl-PZA (2) was dissolved in ethanol together with triethylamine (1 eq., 96 mg, 0.952 mmol). Three equivalents of corresponding alkylamine were added to the reaction mixture and refluxed in ethanol generally for 6 hours. The completion of the reaction was checked by TLC chromatography (eluent: hexane/ethyl acetate, 1:2). The crude product was absorbed on silica by solvent evaporation and purified by flash chromatography (hexane/ethyl acetate gradient elution).

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-Chloropyrazine-2-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Servusova, Barbora; Paterova, Pavla; Mandikova, Jana; Kubicek, Vladimir; Kucera, Radim; Kunes, Jiri; Dolezal, Martin; Zitko, Jan; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 450 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem