Month: July 2021

Related Products of 123-32-0,Some common heterocyclic compound, 123-32-0, name is 2,5-Dimethylpyrazine, molecular formula is C6H8N2, 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.

he 2,5-dimethyl pyrazine (1.08g, 10mmol), methanol (30ml, 742mmol) and 30% sulfuric acid (47ml, 175.4mmol) was added 500ml of four-necked flask, stirring speed, ambient temperature and pressure At the same time at the same speed inwardly slowly dropped 30% H2O2(7ml, 68.4mmol) and a saturated aqueous solution of ferrous sulfate (6.35g, 22.8mmol), the reaction temperature is controlled at 30 ~ 60 , addition was complete, the reaction was completed.The reaction solution was adjusted with sodium hydroxide to pH = 9, was centrifuged, the precipitate portion was washed once with water, the combined aqueous layer was concentrated to dryness, and extracted three times respectively, filtration, filtrate was washed with 250ml of ethyl acetate was distilled under reduced pressure to recover the solvent, the crude product was liguzinediol , column chromatography on silica gel, petroleum ether: ethyl acetate = 3 eluted, recrystallized from ethyl acetate to give white needle crystals 0.52g, yield 31%, purity 99.3%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dimethylpyrazine, its application will become more common.

Reference:
Patent; Nanjing University of Chinese Medicine; Li, Wei; Wen, Hong Mei; Wang, Tianlin; Zhou, Ying; Chen, Lei; (6 pag.)CN103242247; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 22047-25-2, A common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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 250cm3 round-bottom flask equipped with a magnetic stirrer, 2-acetylpyrazine (2.44g, 20.0mmol) was added to a solution of 4 -hexyloxybenzaldehyde (2.06g, 10.0mmol) in EtOH (50cm3). KOH pellets (0.56g, 10mmol) were then added, followed by aqueous NH3 (28%, 40cm3). The resulting orange solution was stirred at room temperature overnight, during which time a suspension had formed. White solid was collected by filtration, washed with H2O and EtOH, and dried in vacuo over P2O5. Yield: 2.28g (55%). Crystals of polymorph 1a was grown by slow evaporation of a solution of 1 in DCM-MeOH over one week. Crystals of polymorph 1b was obtained by slow evaporation of a DCM-MeCN solution containing 1 and AgPF6 (2.0equiv.). 1H NMR (500MHz, CDCl3) delta 9.39(d, J=2.0Hz, 2 H), 8.72 (dd, J=4.5, 1.5Hz, 2 H), 8.54 (dt, J=8.0, 2.0Hz, 2 H), 7.95 (s, 2 H), 7.73 (dd, J=7.0, 2.0Hz, 2 H), 7.49 (dd, J=13.0, 5.0Hz, 2 H), 7.08 (d, J=8.5Hz, 2 H), 4.07 (t, J=6.5Hz, 2 H), 1.86 (m, 2 H), 1.52 (m, 2 H), 1.39 (m, 4 H), 0.95 (t, J=7.0Hz, 3 H) ppm. 13C NMR (125MHz, CDCl3) delta 160.48, 155.21, 150.45, 149.97, 148.25, 134.89, 134.73, 130.04, 128.33, 123.71, 117.23, 115.26, 68.26, 31.60, 29.19, 25.74, 22.64, 14.09ppm. FT-IR (solid, cm-1): 1600m, 1515s, 1376m, 1260s, 1182s, 1110m, 1033s, 1016s, 850w, 826s, 607m. HR-MS: m/z 434.1943 [M+ Na]+ (calc. 434.1957), 412.2132 [M+ H]+ (base peak, calc. 412.2137).

The synthetic route of 22047-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Li; Zhang, Yuan Zhuo; Yang, Chengxiong; Liu; Fettinger, James C.; Zhang, Guoqi; Journal of Molecular Structure; vol. 1110; (2016); p. 19 – 23;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-28-4, These common heterocyclic compound, 33332-28-4, name is 2-Amino-6-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.

Synthesis 2-1 -B 5-bromo-6-chloropyrazin-2-amine 6-Chloropyrazin-2-amine (2.50 g, 19.3 mmol) was stirred in dichloromethane (60 mL) and cooled to OC. N-Bromosuccinimide (2.92 g, 16.4 mmol) was added slowly and the reaction mixture was stirred at 0C for 60 minutes. The reaction mixture was filtered through celite and concentrated to give a brown oil. Purification by flash chromatography, eluting with 0-25% ethyl acetate-hexane, gave the title compound as a yellow solid (1.69 g, 8.16 mmol, 42%). 1HMR (d6-DMSO, 400 MHz) delta 7.65 (s, 1H), 7.1 (br s, 2H). LC-MS (1) rt 1.46 min; m/z (ESI-) 205 (M-H).

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

(g) benzyl 4-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-cyanopiperidine-1-carboxylate To a solution of 1-((benzyloxy)carbonyl)-2-cyanopiperidine-4-carboxylic acid (30 mg, 0.104 mmol) in anhydrous DCM (5 mL) was added HATU (43.5 mg, 0.114 mmol), Et3N (31.56 mg, 0.312 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (20.5 mg, 0.114 mmol). The reaction mixture was stirred at 13 C. for 12 hrs. The reaction was quenched by the addition of water (10 mL), then it was extracted with DCM (10 mL*3), the combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated to afford the crude product, which was purified on silica gel column chromatograph (PE/THF=100%?50%) to give benzyl 4-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-cyanopiperidine-1-carboxylate (40 mg, yield 93%) NMR (400 MHz, METHANOL-d4) delta=8.54 (d, J=2.5 Hz, 1H), 8.35 (d, J=2.5 Hz, 1H), 7.44-7.31 (m, 5H), 5.53 (d, J=4.0 Hz, 1H), 5.21 (d, J=2.5 Hz, 2H), 4.64 (s, 2H), 4.25 (d, J=13.1 Hz, 1H), 2.87-2.84 (m, 1H), 2.88-2.77 (m, 3H), 2.16 (d, J=12.5 Hz, 1H), 2.02-1.91 (m, 2H), 1.66 (dq, J=4.8, 12.9 Hz, 1H).

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

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

Application of 14508-49-7, 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.

t-Butyl 4-hydroxypiperidine-1-carboxylate (3.73 g, 18.0 mmol) was added to a N,N-dimethylformamide suspension (10 ml) of 60% sodium hydride (533 mg, 14.0 mmol), at 0C, and stirring was carried out at room temperature for 30 minutes. Chloropyrazine (1.15 g, 10.0 mmol) was further added at room temperature, and stirring was carried out for 1.5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate and subsequent sequential washing with water and saline, and the resulting organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by silica gel column chromatography to afford t-butyl 4-[(pyrazin-2-yl)oxy]piperidine-1-carboxylate (2.79 g, yield 100%) as a white solid. 1H-NMR (CDCl3, 400 MHz) delta: 8.20 (1H, s), 8.10 (1H, d, J=2.8 Hz), 8.05 (1H, dd, J=2.8 Hz, 1.2 Hz), 5.24-5.18 (1H, m), 3.82-3.76 (2H, m), 3.33-3.27 (2H, m), 2.02-1.97 (2H, m), 1.79-1.70 (2H, m), 1.48 (9H, s). MS (ESI, m/z): 224 (M-tBu+H)+.

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

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2258697; (2010); 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 5-chloropyrazine-2-carboxylate

A 5 N sodium hydroxide solution (2 mL) was added to a solution of methyl 5-chloropyrazine-2-carboxylate (150 mg) in ethanol (4 mL), and the mixture was stirred at room temperature for five hours. Ethyl acetate and water were added to the reaction solution, and the aqueous layer was separated. The aqueous layer was made acidic with concentrated hydrochloric acid. Brine and ethyl acetate were added to the mixture, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated to obtain the title compound (135 mg).1H-NMR (400 MHz, CDCl3) delta (ppm): 1.46 (t, J=7.2 Hz, 3H), 4.51 (q, J=7.2 Hz, 2H), 8.17 (s, 1H), 8.96 (s, 1H).

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

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; US2010/93999; (2010); 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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H2Cl2N2

The titled compound was prepared by the reaction of 2,3-dichloropyrazine (1.0 g, 6.71 mmol) with N-methylpiperazine (988 mg, 9.86 mmol) in acetonitrile (25 mL) at RT as per the procedure described in Step 1 of Intermediate 7 to yield 658 mg of the product; 1H NMR (300 MHz, CDCI3) delta 2.40 (s, 3H), 2.58-2.65 (m, 4H), 3.52 (s, 4H), 7.86 (d, J = 2.1 Hz, 1H), 8.09 (s, 1H).

According to the analysis of related databases, 4858-85-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; SHELKE, Sandeep Yadunath; PARDESHI, Shailesh Ramesh; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (181 pag.)WO2017/21879; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-28-4, 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. 33332-28-4, name is 2-Amino-6-chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step 1: 2-amino-6-methoxypyrazine. To a stirred solution of methanol (89 muL; 2.2 mmol) in dioxane (1 mL) was added sodium hydride (53 mg; 2.2 mmol). After stirring for 30 minutes, 2-amino-6-chloropyrazine (258 mg; 2.0 mmol) was added and the reaction was heated to 90° C. After stirring for 12 hours, the reaction was cooled to room temperature, diluted with 30 mL of ethyl acetate and washed with aqueous 10percent sodium carbonate (1*30 mL), and brine (30 mL), then dried (MgSO4), and filtered. The crude product was purified using the Biotage 12i cartridge eluding with hexane and ethyl acetate (3:1) to yield a white solid (11percent yield).

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; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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 2,3-dichloropyrazine (1.50 g, 10.07 mmol) and phenylboronic acid (1.23 g, 10.07 mmol) in 35 mL of DME was added Na2C03 (1.07 g, 10.07 mmol) in 15 mL of water. N2 gas was bubbled through the reaction mixture for 15 min then the flask was equipped with a condenser and purged with N2 for another 15 in before adding tetrakis(triphenylphosphine)palladium (581.75 mg, 0.503 mmol). The resulting reaction mixture was heated to reflux (85C) and allowed to stir overnight. The reaction was cooled to rt and diluted with 80 mL of water then extracted three times with DCM. The combined organic extracts were dried with MgS04, filtered and concentrated under reduced pressure. The resulting yellow residue was purified via silica gel chromatography (0 – 30% ethyl acetate/hexanes) to provide the desired product (1.39 g, 72%) as a white solid.

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANDRES GIL, JOSE IGNACIO; LETAVIC, MICHAEL A; RECH, JASON C; RUDOLPH, DALE A; SOYODE-JOHNSON, AKINOLA; CHROVIAN, CHRISTA C; (158 pag.)JP2017/527588; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-55-1, 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 5521-55-1 as follows.

(1) Synthesis of t-butyl 5-methylpyrazine-2-carboxylateA boron trifluoride-diethyl ether complex (91.7 muL) was added dropwise to a suspension of 2-methylpyrazine-5-carboxylic acid (1 g) and tert-butyl 2,2,2- trichloroacetimidate (4.75 g) in THF (20 mL) under ice-cooling. The reaction solution was warmed to RT, followed by stirring for 2 h. A saturated NaCl solution and EtOAc were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous MgSO4, and the insoluble matter was separated by filtration. The filtrate was concentrated and purified by silica gel columnchromatography to obtain the title compound (1.4 g). l H-NMR (CDCI3 ) delta (ppm): 1.65 (s, 9H), 2.65 (s, 3H), 8.57 (d, J = 1.2 Hz, IH), 9.10 (d, J = 1.6 Hz, IH).

According to the analysis of related databases, 5521-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD; ELLARD, John Mark; FARTHING, Christopher Neil; HALL, Adrian; WO2011/9898; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem