Tag: M.W=100-200

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

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

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

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

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

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 5521-58-4,Some common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

Methyl 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-chloronicotinate (90 mg, 0.23 mmol), 5-methylpyrazin-2-amine (38 mg, 0.35 mmol, as described in ltoh et al., 2002), cesium carbonate (153 mg, 0.47 mmol), 4,5-bis(diphenyl phosphino)-9,9-dimethylxanthene (11 mg, 8 mol%), and tris(dibenzylidene acetone)dipalladium chloroform complex (10 mg, 4 mol%) were added to an oven-dried microwave reactor vial (2 mL) which was capped and flushed with nitrogen. Anhydrous toluene (1.35 mL) was added and nitrogen was bubbled through the stirred solution for 10 minutes. The mixture was heated at 130C for 30 minutes by microwave irradiation. The solution was cooled, diluted with dichloromethane-methanol and adsorbed onto a 2g lsolute SCX-II column. The resin was washed with methanol, then with 2M ammonia in methanol. The basic fractions were concentrated and the residue was purified by preparative TLC, eluting with 10% methanol – dichloromethane) to give methyl 6-(5- methylpyrazin-2-ylamino)-4-(1-Boc-piperidin-4-ylmethylamino)nicotinate (35 mg) as a light green powder.LCMS (3) Rt 3.62 min; m/z (ESI+) 457 (MH+).The material was dissolved in dichloromethane (1mL) at 0C and trifluoroacetic acid (8 drops) was added. The temperature was allowed to rise to ambient. After 2.5 hours the mixture was adsorbed onto a 2g lsolute SCX-II column. The resin was washed with methanol, then with 2M ammonia in methanol. The basic fractions were concentrated. Preparative TLC, eluting with 1 % concentrated ammonia – 10% methanol – 89% dichloromethane, gave methyl 6-(5-methylpyrazin-2-ylamino)-4-(piperidin-4- ylmethylamino)nicotinate (18 mg, 22% over 2 steps) as a yellow powder.1H NMR (500 MHz, DMSO) delta 1.17-1.24 (2H, m), 1.66 (2H, d, J = 12 Hz), 1.68-1.79 (1 H, m), 2.40 (3H, s), 2.48 (2H, t, J = 12 Hz), 2.98 (2H, d, J = 12 Hz), 3.09 (2H, t, J = 6 Hz), 3.22 (1H, t, J = 6 Hz), 3.80 (3H, s), 7.11 (1H, s), 8.00 (1H, t, J = 5.5 Hz), 8.14 (1H, s), 8.54 (1H, s), 8.84 (1H, s), 9.90 (1H, br s). LCMS (3) Rt 1.65 min; m/z (ESI+) 357 (MH+).

The synthetic route of 5521-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); 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. 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, A new synthetic method of this compound is introduced below., name: Methyl 3-Hydroxy-2-pyrazinecarboxylate

458 g (3 mol, 1 eq) of methyl 3-hydroxy-2-pyrazinecarboxylate and 532 g (3 mol, 1 eq) Bromosuccinimide were successively added to 5 L of acetonitrile,The mixture was stirred at 25 C for 12 hours,After TLC detection reaction was complete,The reaction was stopped,filter,Filter cake vacuum drying at room temperature,To give 554 g of methyl 6-bromo-3-hydroxy-2-pyrazinecarboxylate (including tautomer 6-bromo-3-oxo-3,4-dihydro-2-pyrazinecarboxylic acid Methyl ester),The yield was 85%. 6-Bromo-3-hydroxy-2-pyrazinecarboxylic acid methyl ester

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; Qingdao Hangdao District Chinese Medicine Hospital; Lu, Yanmin; (5 pag.)CN105732524; (2016); A;,
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. 41110-33-2, name is Methyl 5-methylpyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 41110-33-2

A solution of LAH (164.0 mL, 0.164 mol, 1.0 M in THF, 0.5 equivalents) was added to a suspension of methyl 5-methylpyrazine-2-carboxylate (50 g, 0.328 mol, 1.0 equiv.) in anhydrous THF (750 mL) at -78C. (The internal temperature was kept below -72 C during the addition of LAH). Upon completion of addition, the reaction mixture was left to stir at -78 C for a further 20 min and then quenched with glacial AcOH (50.0 mL) at the same temperature. The resulting mixture was warmed to RT and the volatiles were removed in vacuo. The residue was dissolved in hydrochloric acid (1.5 N, 500 mL) and extracted with DCM (2 x 2 L). The extracts were combined, washed with a saturated aqueous NaHCO3solution (2 x 500 mL), dried over anhydrous Na2SO4, and concentrated in vacuo, to yield the product as a brown oil. The residue was purified by column chromatography (silica gel 60-120 mesh) eluting with a gradient of 10% EtOAc in petroleum ether to provide the title compound as a pale yellow liquid (21.3 g, 53 %). TLC Info: (9.0/1.0 Petroleum ether/EtOAc).1H NMR (400 MHz, CDCl3) delta 10.14 (s, 1H), 9.07 (d, J = 1.5 Hz, 1H), 8.63 (d, J = 1.4 Hz, 1H), and 2.70 (s, 3H). LCMS (ESI positive ion) m/z: 123 (M+H)+.

The synthetic route of 41110-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4744-50-7, 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 4744-50-7 as follows.

3-(5,7-Dimethyl-1,8-naphthyridin-2-yl)carbamoylpyrazine-2-carboxylic acid, m.p. 255 C. with decomposition, can be prepared by reacting pyrazine-2,3-dicarboxylic acid anhydride with 2-amino-5,7-dimethyl-1,8-naphthyridine in anhydrous dimethylformamide at a temperature of about 100 C. 2-Amino-5,7-dimethyl-1,8-naphthyridine, which melts at 225-226 C., can be prepared according to the method of J. Bernstein et al, J. Amer. Chem. Soc., 69, 1151 (1947).

According to the analysis of related databases, 4744-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rhone-Poulenc S.A.; US4016274; (1977); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem