Month: March 2021

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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromo-5-iodopyrazine

A mixture of 2-bromo-5-iodopyrazine (200mg, 0.704mmol), cesium carbonate (400mg, 1.23mmol) and 2R methyl piperazine (85mg, 0.85mmol) in DMF (1 OmI) was stirred at 1000C overnight. The reaction was cooled and solvent evaporated.Water (100ml) was added and insoluble solid was filtered, then dissolved in MeCb (100ml), dried over Na2SO4, filtered and solvent evaporated yielding product (205mg, 95%)

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 622392-04-5.

Reference:
Patent; SCHERING CORPORATION; WO2008/153858; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, 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 27398-39-6, category: Pyrazines

To a suspension of sodium hydride (278 mg, 6.95 mmol, 60percent in oil) in DMF (10 mL) was added lH”-pyrazole (279 mg, 4.11 mmol) and the resulting mixture stirred at room temperature for 30 mins. 3-Chloropyrazine-2-carboxylic acid (500 mg, 3.16 mmol) was added and the mixture was heated to 60 ¡ãC for 2 h. After cooling to room temperature, water (20 mL) was added and the mixture extracted with 5percent MeOH in DCM (3 x 20 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to give Intermediate E as a solid. LRMS m/z (M+H) 191.0 found, 191.0 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloropyrazine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (0 pag.)WO2016/85784; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6905-47-1, These common heterocyclic compound, 6905-47-1, name is 2-Amino-6-methoxypyrazine, 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.

Example 55 (3S)-2-(2R)-3-Cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-1-methyl-N-[6-(methyloxy)-2-pyrazinyl]-3-pyrazolidinecarboxamide 6-(methyloxy)-2-pyrazinamine (67.4 mg, 0.539 mmol). LC-MS (ES) m/e 435.4 (M+H)+.

Statistics shows that 2-Amino-6-methoxypyrazine is playing an increasingly important role. we look forward to future research findings about 6905-47-1.

Reference:
Patent; Glaxosmithkline LLC; Aubart, Kelly M.; Benowitz, Andrew B.; Fang, Yuhong; Hoffman, James; Karpinski, Joseph M.; Knox, Andrew Nicholson; Liao, Xiangmin; Qin, Donghui; Shi, Dongchuan; Spletstoser, Jared T.; US2013/345120; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-83-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 36070-83-4 name is Ethyl 5-bromopyrazine-2-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Embodiment 66 ethyl 5-((4,4-dimethylthiochroman-6-yl)ethynyl)pyrazin-2-carboxylate ethyl 5-bromopyridazin-2-carboxylate (600mg, 2.61mmol) and 6-ethynyl-4,4-dimethylbenzothiopyran (635mg, 3.13mmol) were added to a flask, followed by addition of Pd(PPh3)2Cl2 (66mg, 0.094mmol) and CuI (36mg, 0.188mmol). After the flask was purged with argon for 3 times to remove oxygen, 6mL dry DMF and 0.4mL dry Et3N were added via syringe. Then the reaction was continued at 80C for 8 h and monitored by TLC. After completion of the reaction, the reaction was quenched with saturated ammonium chloride solution. The mixture was diluted with ethyl acetate, washed with saturated ammonium chloride solution and saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography (PE:EtOAc = 50:1) to give WYC-322 (656mg, 71.5%). 1H NMR (500 MHz, CDCl3) delta 9.20 (d, J = 1.4 Hz, 1H), 8.76 (d, J = 1.4 Hz, 1H), 7.58 (d, J = 1.7 Hz, 1H), 7.23 (dd, J = 8.2, 1.8 Hz, 1H), 7.04 (d, J = 8.2 Hz, 1H), 4.46 (q, J = 7.1 Hz, 2H), 3.02 – 2.97 (m, 2H), 1.92 – 1.87 (m, 2H), 1.41 (t, J = 7.1 Hz, 3H), 1.29 (s, 6H). 13C NMR (126 MHz,CDCl3) delta 163.65, 146.68, 145.70, 143.08, 142.31, 140.30, 136.14, 130.54, 129.51, 126.74, 116.00, 97.55, 85.68, 62.37, 36.91, 32.99, 29.89, 23.27, 14.31. ESI(+)-MS: 353.5 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-bromopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences; Huazhong University of Science and Technology; CAO, Xin; YU, Biao; WANG, Ning; CHEN, Junwei; (88 pag.)EP3428155; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4949-13-7,Some common heterocyclic compound, 4949-13-7, name is 2-Fluoropyrazine, molecular formula is C4H3FN2, 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.

[0222] To a mixture of (A)-4-( l -aminocthyljhcnzonitrilc (1.0 g, 6.8 mmol, 1.0 equiv) and IPA (15 mL) in a microwave vial (20 mL) were added 2-fluoropyrazine (0.81 g, 8.2 mmol, 1.2 equiv) and DIPEA (2.1 g, 16.4 mmol, 2.4 equiv). The vial was sealed and heated at 170 C in a microwave reactor for 4 h. The mixture was concentrated onto 5 g of Si02 and purified by silica gel chromatography (40 g column, 0-10% MeOH in DCM) to provide (/?)- 4-(l-(pyrazin-2-ylamino)ethyl)benzonitrile. LRMS (ES) m/z 225.1 (M+H). 1 H-NMR (Methanol-74, 400 MHz, ppm) d 7.92 (t, J = 1.7 Hz, 1H), 7.85 (dd, 7 = 2.9, 1.5 Hz, 1H), 7.70 – 7.63 (m, 2H), 7.61 (d, 7 = 2.9 Hz, 1H), 7.58 – 7.52 (m, 2H), 5.08 (q, 7 = 7.1 Hz, 1H), 1.54 (d, 7 = 7.0 Hz, 3H).

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

Reference:
Patent; CYTOKINETICS, INC.; MORGAN, Bradley P.; VANDERWAL, Mark; CHUANG, Chihyuan; (0 pag.)WO2020/5888; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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. COA of Formula: C4H4ClN3

6-Chloronicotinoyl chloride (1.00 g, 5.68 mmol) in dry DCM (4 mL) was added dropwise to an ice cold solution of 1 -methyl- 1,4-diazepane (648 mg, 5.68 mmol) and NEt3 (1.18 mL, 8.52 mmol) in dry DCM (16 mL). The mixture was allowed to attain rt and stirred for 2 hours. Saturated aq Na2CO3/water (1 : 1, 40 mL) was added and the mixture was extracted with DCM (2x 30 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated to1.33 g of a light brown oil. MS (ESI+) for C12H 16C1N3O m/z 254 (M+H)+. Part of the material (294 mg, 1.16 mmol) was added to 6-chloropyrazin-2-amine (150 mg, 1.16 mmol), palladiumacetate (13 mg, 0.06 mmol), (+/-)-BINAP (36 mg, 0.06) and K2CO3 (2.4O g, 17.4 mmol) in dry toluene (12 mL) and stirred at 120 0C for 1.5 hours. The solvent was evaporated and the crude material was extracted with water/brine (1 : 1; 50 mL) and EtOAc (2x 50 mL). The organic layers were combined and concentrated. The title compound was obtained after purification by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10, MeCN), as a light brown solid (55 mg). MS (ESI+) for C16H19C1N6O m/z 347 (M+H)+.HPLC 92percent(System A), 85percent(System B).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33332-28-4, its application will become more common.

Reference:
Patent; BIOVITRUM AB (PUBL); WO2007/147874; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

3,5-Diamino-6-chloropyrazine-2-carboxylic acid Methyl-3,5-diamino-6-chloropyrazine-2-carboxylate (8.5 g, 41.9 mmol) is dissolved in dioxane (200 mL), sodium hydroxide (1 M in water, 125 mL, 125 mmol) added and the mixture stirred overnight at room temperature. The reaction mixture is acidified to pH 5 with 4 M hydrochloric acid and concentrated to one third of the initial volume. The resulting solid is collected by filtration, washed with water and dried under vacuum at 50¡ã C. Yield: 7.4 g ESI mass spectrum: [M+H]+=189

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WIEDENMAYER, Dieter; HECKEL, Armin; HAMPRECHT, Dieter; US2015/45326; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 54013-07-9, name is 5-Methoxypyrazin-2-amine, 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. category: Pyrazines

Example 3 Preparation of 5-(6-((5-methoxypyrazin-2-yl)carbamoyl)-2-methylbenzofuran-4-yloxy)-N,N-dimethylpyrimidine-2-carboxamide (3) The title compound (3) was prepared by a method analogous to that described in Example 1 using 5-methoxypyrazin-2-amine and ethyl 4-(2-(dimethylcarbamoyl)-pyrimidin-5-yloxy)-2-methylbenzofuran-6-carboxylate (I-2a). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.49 (s, 3H), 2.99 (s, 3H), 3.15, (s, 3H), 3.98 (s, 3H), 6.28 (s, 1H), 7.51 (s, 1H), 7.89 (s, 1H), 7.94 (s, 1H), 8.30 (s, 1H), 8.50 (s, 2H), 9.17 (s, 1H). m/z=449.1 (MH+)

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

Reference:
Patent; Pfizer Inc; US2010/234285; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 74290-69-0, name is 5-Bromo-6-methylpyrazin-2-amine, 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 74290-69-0, Safety of 5-Bromo-6-methylpyrazin-2-amine

Step 1: Synthesis of 1-38.1To a solution of 1-35.4 (495 mg, 2.39 mmol) in THF (5ml) in a microwave vial is added hexamethyldistannane (0.55 ml, 2.64 mmol) followed by bis(triphenylphosphine)palladium(II) chloride (168 mg, 0.239 mmol). The reaction mixture is degassed with argon, capped, and stirred at 85 C for 16 hrs. R-32 (450 mg, 2.39 mmol) is added followed by tetrakis(triphenylphosphine)palladium (0) (276 mg, 0.239 mmol). The reaction vessel is degassed with argon, then capped and heated at 85 C for 16 hours. The reaction mixture is passed through a plug of Celite and rinsed with DCM. The filtrate is concentrated in vacuo and purified by flash chromatography (Si02, 0-5% MeOH/DCM) to afford the title intermdiate (160 mg); m/z 281.3 [M+l]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-6-methylpyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John, D.; LIU, Weimin; LO, Ho Yin; LOKE, Pui Leng; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee, M.; WO2012/40137; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5049-61-6, These common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, 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 suspension of 2-aminopyrazine (1) (20.0 g, 210.28 mmol) in dry DCM (200 mL) was added N-bromosuccinimide (37.42 g, 210.28 mmol) in portion wise at cold condition under nitrogen atmosphere and stirred at RT for 1.5 h. Reaction mixture was concentrated under vacuum, added 30 mL of water and filtered the crude solid. Filtrate was extracted with DCM:MeOH (9: 1, 50 mL X 4). Combined organic layers was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and concentrated under vacuum. Combined crude solids were purified by column chromatography over silica gel 230-400 mesh using 0-1 % of methanol in dichloromethane as an eluent to afford product 2 (19.0 g, 52.7%) as yellow solid.1H NMR (400 MHz, DMSO-d6): delta 8.03 (d, J = 1.28 Hz, 1H), 7.68 (d, J = 1.32 Hz, 1H), 6.66 (s, 2H). LC-MS APCI: Calculated for C4H4BrN3: 174.00; Observed m/z [M+H]+ 176.00.

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; UNIVERSITY OF CAPE TOWN; WATERSON, David; WITTY, Michael John; CHIBALE, Kelly; STREET, Leslie; GONZALEZ CABRERA, Diego; PAQUET, Tanya; (36 pag.)WO2017/9773; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem