Month: April 2021

Adding a certain compound to certain chemical reactions, such as: 33332-28-4, name is 2-Amino-6-chloropyrazine, 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 33332-28-4, COA of Formula: C4H4ClN3

N-bromosuccinimide(NBS) (27.5 g, 155 mmol) was slowly added, was warmed up to room temperatureovernight (18 hours) and the mixture was stirred. Water was added thereto andthe product was extracted with ethyl acetate (¡Á 3). The organic layer waswashed with water (¡Á 1) and saturated brine (¡Á 1), and dried over anhydroussodium sulfate. After filtration, the filtrate was concentrated under reducedpressure, and the residue was purified by silica gel flash columnchromatography (n- hexane / ethyl acetate = 3/1),2-amino-3,5-dibromo-6-chloropyrazine (4) (16.8 g , 58.5 mmol, 94.7percent) as ayellow solid

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, 2-Amino-6-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JNC CORPORATION; TOKYO MEDICAL AND DENTAL UNIVERSITY; INOUYE, SATOSHI; SAHARA, YUIKO; YOSHIDA, SUGURU; HOSOYA, TAKAMITSU; (47 pag.)JP5837973; (2015); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products 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 methyl 3 -(4-methanesulfonylphenyl)-2-methyl-3 -oxopropanoate (1 g, 3.7 mmol) and 2-hydrazinylpyrazine (0.41 g, 3.7 mmol) in ethanol (15 mL) was heated in a pressure tube for 2 hours at 70 C, followed by 72 hours at about 25 C and 24 hours at 70 C. The reaction mixture was cooled to about 25 C and the solvent was removed under reduced pressure to afford a brown oil. Thecrude oil was purified by silica gel chromatography eluting in 0-30 % methanol: ethyl acetate, followed by an SCX-2 cartridge eluting in methanol to give the title compound as a yellow solid (40 mg, 3 %). LC-MS tR = 0.95 mi [M+H] = 331, ?H NMR (500 MHz, Methanol-d4) 9.56 (s, 1H), 8.59 – 8.50 (m, 2H), 8.14 (d, J = 8.5 Hz, 2H), 8.05 (d, J = 8.5 Hz, 2H), 3.22 (s, 3H), 2.16 (s, 3H).

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

Reference:
Patent; CARDIOXYL PHARMACEUTICALS, INC.; THE JOHNS HOPKINS UNIVERSITY; KALISH, Vincent, J.; BROOKFIELD, Frederick, A.; COURTNEY, Stephen, M.; FROST, Lisa, M.; TOSCANO, John, P.; GUTHRIE, Daryl, A.; NORTH, Carl, L.; (442 pag.)WO2015/183839; (2015); 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 59489-71-3 as follows. HPLC of Formula: C4H4BrN3

To a solution of compound (ii) (1.98 g, 11.46 mmol) in DMSO (20 ml) was added iodine crystals (3.49 g, 13.75 mmol) at RT and the resulting mixture was heated to 100C for 4 h and then stirred at RT for 12 h. Water (20 ml) was then added and the reaction mixture was extracted with ethyl acetate (60 ml X 4). Combined organic layers were washed with water (10 ml X 3), saturated sol. of sodium metabisulphite (5 ml X till Iodine color disappears), Brine solution (10 ml), dried over anhydrous Na2S04 and concentrated under vacuum. The crude material was purified by column chromatography over silica gel 230-400 mesh by using ethyl acetate in petroleum ether as an eluent to yield compound (iii) (260 mg, 7.56%) as white solid.

According to the analysis of related databases, 59489-71-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF CAPE TOWN; MMV MEDICINES FOR MALARIA VENTURE; YOUNIS, Yassir; CHIBALE, Kelly; WITTY, Michael, John; WATERSON, David; WO2013/121387; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4774-14-5, 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 4774-14-5 as follows.

Synthesis o -chloro-6-phenylpyrazine[00145] To a solution of 2,6-dichloropyrazine (2.0 equiv.) in 3 : 1 DME:2M aqueous sodium carbonate (0.125 M) was added phenylboronic acid (1.0 equiv.) then PdCl2(dppf) ¡¤ DCM adduct (0.1 equiv.). The reaction was heated in the microwave at 120 C for 15 minutes. The crude reaction mixture was diluted with ethyl acetate and washed with sat. aq. sodium bicarbonate then sat. NaCl. The organic phase was dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel column chromatography with heptanes to 30% ethyl acetate in heptanes to give 2- chloro-6-phenylpyrazine in 75% yield. LC/MS (m/z): 191.0 (MH+), R, = 1.00 min.

According to the analysis of related databases, 4774-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BURGER, Matthew; DING, Yu; HAN, Wooseok; LINDVALL, Mika; NISHIGUCHI, Gisele A.; RICO, Alice; SMITH, Aaron; TANNER, Huw; WAN, Lifeng; WO2012/4217; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 153800-11-4, A common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, molecular formula is C6H4N2, 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.

To a solution of 197(100mg, 0.3 i9mmol)) and 10(36.6mg, 0.35 Immol) in 2OmL of Et3N was added Pd(PPh3)2C12 (11.21mg, 0.Ol6mmoi)and Cul (608mg, 0.O32mmol)). The mixture was protected under N2 atmosphere, then was heated at 70C for 4 hours. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep4IPLC to give the target productCompound 80(25mg, yield: 27.1 %).LCMS: m/z 290 (,ff:[)-F;?H NMR (400 MTIz, CDCl) 8 78 (hi 111), 8 62.-8 55 (mn 21fl 8 21 (S 11-fl 7 9? s il-fl 7.83 (s. 1H), 7.76-7.73 (m, 1H), 7.357.32 (m, 1H).

The synthetic route of 153800-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 875781-43-4,Some common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4BrN3, 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 1To a reaction vial, 2-bromo-5H-pyrrolo[2,3-b]pyrazine (1 g, 0.00505 mol) was added in TFA (10 ml). Hexamine (1.06 g, 0.00757 mol) was added and reaction mixture was heated to 80 C in microwave for 15 min. After completion of the reaction, the reaction mixture was poured into aq. Na2C03 solution. Solid obtained was filtered, dried and purified using column purification by eluting with 3-5% EtOAc in Hexanes to yield 0.450 g of 2-bromo-5H- pyrrolo[2,3-b]pyrazine-7-carbaldehyde.

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; VERNER, Erik; WO2012/158785; (2012); 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. 32111-21-0, name is 2-Iodopyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H3IN2

Example 59; 3-fl-f4-Chloro-phenyl’)-6-oxo-2-(‘4-pyrazin-2-yl-phenv?-.6-dihvdro-purin-9-yll-benzene sulfonamide; [00194] A solution of 3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-l-yl}-benzene sulfonamide (prepared as described in example 25, 0.500 g, 0.82 mmol) in N,N- dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.250 g, 1.24 mmol), cesium carbonate (0.530 g, 1.65 mmol), Pd(dppf)2Cl2 (0.06 g, 0.08 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 50 0C for 12 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3*). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and’ purified by column chromatography over silica gel (60 – 120 mesh) to afford 3-[l-(4-chloro-phenyl)-6-oxo-2-(4-pyrazin-2-yl-phenyl)-l,6-dihydro-purin- 9-yl]-benzene sulfonamide. 1H NMR (DMSO-dbeta, 400 MHz) delta 9.24 (m, IH), 8.69 (m, IH), 8.63 (m, IH), 8.30 (m, IH), 8.02-8.08 (m, 2H), 7.94 (m, IH), 7.82 (m, IH), 7.43-7.58 (m, 8H), 7.15 (br, 2H); LC-MS calculated for C27H18ClN7O3S (MH-H+) 556.1, found 555.9.

The synthetic route of 32111-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 21279-64-1, These common heterocyclic compound, 21279-64-1, name is 5-Chloropyrazine-2-carboxamide, 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: 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).

The synthetic route of 21279-64-1 has been constantly updated, and we look forward to future research findings.

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

Related Products of 136927-64-5, 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. 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Compound C18 (135 mg, 0.630 mmol), 1-chloropyrrolo[1,2-a]pyrazine (120 mg,0.760 mmol), cesium carbonate (308 mg, 0.945 mmol), palladium(ll) acetate (28 mg,0.13 mmol), and di-teit-butyl[3,4, 5,6-tetramethyl-2? 4? 6-tn (propan-2-yl)biphenyl-2- yl]phosphane (120 mg, 0.250 mmol) were combined in 1,4-dioxane (5 mL), and the reaction mixture was heated to 120 00. After 3 hours, it was cooled to room temperature and subjected to silica gel chromatography (Eluent: 4% methanol in ethylacetate) to provide the racemic product, which was subsequently separated into its component atropenantiomers via supercritical fluid chromatography (Column: Chiralpak AD-H, 5 pm; Eluent: 3:7 methanol I carbon dioxide). The first-eluting atropenantiomer was designated as 12, and exhibited a negative (-) rotation. Yield: 34.9 mg, 0.110 mmol, 17%. LCMS m/z331.1 [M+H]. 1H NMR (400 MHz, CDCI3)o 9.01 (brs, 1H), 7.62(dd, J=4.9, 0.8 Hz, 1H), 7.47 (dd, J=2.4, 1.4 Hz, 1H), 7.30 (d, J=2.2 Hz, 1H), 7.27-7.24 (m, 1H), 7.09 (d, J=4.9 Hz, 1H), 7.05 (d, J=6.3 Hz, 1H), 6.99-6.97 (m, 1H), 6.86 (dd, J=4.1, 2.7 Hz, 1H), 2.46 (5, 3H), 2.11 (5, 3H), 2.02 (5, 3H). The second-eluting atropenantiomer was designated as 13, and was found to have a positive (+) rotation. Yield: 30mg, 88 pmol, 14%. LCMS m/z331.1 [M+H]. 1H NMR (400 MHz, CDCI3) oe9.02 (brs, 1H), 7.63 (dd, J=4.7, 0.8 Hz, 1H), 7.46 (dd, J=2.5, 1.4 Hz, 1H), 7.30 (d, J=2.3 Hz, 1H), 7.27-7.25 (m, 1H), 7.10 (d, J=4.9 Hz, 1H), 7.05 (d, J=8.2 Hz, 1H), 6.89 (dt, J=4.1, 1.2 Hz, 1H), 6.86 (dd, J=4.1, 3.5 Hz, 1H), 2.47 (5, 3H), 2.11 (5, 3H), 2.01 (5, 3H).

The synthetic route of 1-Chloropyrrolo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 33332-25-1

Trimethylaluminium (2M in toluene, 7.44 ml, 14.88 mmol) was added dropwise to a stirred suspension of 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine, HCl (1.70 g, 5.95 mmol) and methyl 5-chloropyrazine-2-carboxylate (1.03 g, 5.95 mmol) in anhydrous toluene (29.8 ml) at ambient temperature. The resulting solution was then stirred under nitrogen at ambient temperature for 18 h. The reaction mixture was quenched with methanol (5 mL) and HCl (2M aqueous solution), diluted with water (200 mL) and extracted with EtOAc (3¡Á150 mL). The organics were washed with water (200 mL), brine (200 mL) dried over MgSO4, filtered and concentrated. On evaporation a precipitate was formed which was collected by filtration, washed with MeOH (20 mL) and air dried to afford the desired compound (1.65 g, 71%) as an orange solid, which was used without further purification. 1H NMR (500.13 MHz, DMSO-d6, 373K) delta 3.78 (6H, s), 5.12 (2H, s), 5.94 (1H, s), 6.46 (1H, s), 6.62 (2H, s), 8.87 (1H, s), 9.09 (1H, s), 10.99 (1H, s), 11.24 (1H, s). MS: m/z 390 (MH+) Mean of n=1, FGFR Kinase assay-Caliper Echo Dosing, IC50 0.060 muM.

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 33332-25-1.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem