Category: Pyrazines

Electric Literature of 13134-38-8, These common heterocyclic compound, 13134-38-8, name is 3,6-Dimethylpyrazin-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.

[0093] To a stuffed solution of 280 mg (2.0 mmol) of thiophene-2,5-dicarbaldehyde in 6 mL of THF and 0.2 mL of water was added sodium borohydride (54 mg, 1.4 mmol). The reaction was stirred for 20 mm at rt. Water (5 mL) was added and the mixture was stirred for 10 mm and extracted with EtOAc (3 x). The combined organic layers were dried over Na2504, filtered and evaporated. The crude material was diluted with 10 mL of acetonitrile and cooled to 0 C. Triethylamine (0.89 mL) and methanesulfonyl chloride (0.40 mL) were added and the mixture was stilTed for 1 h at 0 C and then 1 h at rt. The mixture was treated with satd. aq. NaHCO3 and extracted with EtOAc (3 x). The combined organic layers were dried over Na2SO4, filtered and evaporated to provide 657 mg of crude thiophene-2,5-diylbis(methylene) dimethanesulfonate. A mixture of 62.1 mg of the crude mesylate, 114 mg of K2C03, and 50 mg of 3,6-dimethylpyrazin-2-amine in 1 mL of DMF was heated at 110 C in a sealed tube with stirring for 48 h. The mixture was cooled to rt, diluted with water, and extracted with EtOAc (3x). The combined organic layers were dried over Na2SO4, filtered and evaporated. Purification by column chromatography (100% EtOAc) provided 7.3 mg of the title compound. MS (ESj:[M+H] 355.3; [M+Na] 377.4; MS (ES): [M-H] 353.3.

The synthetic route of 13134-38-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROPORE THERAPIES, INC.; WRASIDLO, Wolfgang; STOCKING, Emily, M.; (53 pag.)WO2016/40780; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 109838-85-9,Some common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, molecular formula is C9H16N2O2, 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.

[00374] 100 g (0.543 mol) of 1 (100 g, 5.4 mol) was taken up in THF (1000 mL) and cooled to -78 ¡ãC. 228 mL (0.570 moles) of n-BuLi (2.5M in THF) was added dropwise over 30 minutes. Then the solution was stirred vigorously for an additional 30 minutes. 81 g of methyl iodide (0.57 mol) was diluted to 250 mL with THF and cooled to -78 ¡ãC. The methyl iodide was then added dropwise over 30 minutes. Following completion of the addition of methyl iodide, the reaction was stirred at -78 ¡ãC for 2 hours. 1L of diethyl ether was then added to the mixture, followed by 500 mL of H20. The reaction was then warmed to room temperature. The aqueous layer was extracted multiple times with diethyl ether and the organic layer were combined, washed with saturated sodium thiosulfate, once with brine, and dried over MgSC>4. The organics were concentrated under vaccum to give residue which was purified by chromatography with gradient of 50: 1 to 20: 1 petroleum ether: diethyl ether to yield 110 g (80.5percent) of 2 (pale yellow oil). XH NMR: (400 MHz, CDC13-J) ppm 0.60 – 0.72 (m, 3 H), 0.94 – 1.03 (m, 3 H), 1.26 – 1.35 (m, 3 H), 2.07 – 2.30 (m, 1 H), 3.53 – 3.70 (m, 6 H), 3.89 (br. s., 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, its application will become more common.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; VERDINE, Gregory, L.; HILINSKI, Gerard; WO2014/159969; (2014); 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H4ClN3

Example 5 N-(6-Chloro-pyrazin-2-yl)-7-fluoro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 4.1 g (15 mmols) of methyl 7-fluoro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 2.3 g (18 mmols) of 2-amino-6-chloropyrazine were reacted in 200 ml of xylene analogous to Example 2 and worked up in analogy thereto. 3.8 g (66percent of theory) of N-(6-chloro-pyrazin-2-yl)-7-fluoro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were obtained. IR (KBr): 1645 cm-1 (CO amide).

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

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 2423-65-6, A common heterocyclic compound, 2423-65-6, name is Pyrazine 1-oxide, molecular formula is C4H4N2O, 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 2:; Palladium-Catalyzed Direct Arylation with Aryl Chlorides and Bromides.; To a dried flask was added the diazine N-oxide (1.0 to 3.0 equiv.), K2CO3 (2.0 equiv.), Pd(OAc)2 (5 mol %) and HP(t-Bu)3BF4 (15 mol %). If the arylhalide is a solid, it is added at this point (1.0 equiv.). The flask and its contents were then purged under nitrogen for 10 minutes. If the aryl halide is a liquid, it is added via syringe after purging, followed by the addition of degassed dioxane (to produce a reaction concentration of 0.3 M relative to the halide). The reaction mixture was then heated at 110 C. until the reaction was complete, after which the volatiles were removed under reduced pressure and the residue was purified via silica gel column chromatography.; 2-p-Tolylpyrazine N-oxide (81) Synthesised according to general procedure 2 employing the corresponding aryl bromide and chloride or 60 with the corresponding aryl iodide. Purification via silica gel column chromatography using 100% DCM then a mixture of 20% Acetone/DCM gave a white solid, 72% (from the bromide), 75% (from the chloride) and 77% (from the iodide). 1H NMR (300 MHz, CDCl3, 293K, TMS): delta 8.63 (1H, s), 8.37 (1H, s), 8.20 (1H, s), 7.72 (2H, d, J=8.1 Hz), 7.33 (2H, d, J=7.8 Hz), 2.43 (3H, s). 13C NMR (75 MHz, CDCl3, 293K, TMS): 148.2, 145.2, 144.6, 140.8, 134.2, 129.8, 129.0, 125.9, 21.5.

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; University of Ottawa; US2008/132698; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 345311-03-7, 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. 345311-03-7, name is tert-Butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of tert-butyl 6,8-dihydro-5H-imidazo[1,2-a]pyrazine-7-carboxylate (1.0 g, 4.48 mmol), 8-chloro-7-fluoro-6-iodo-isoquinolin-3-amine (1.5 g, 4.65 mmol), potassium carbonate (1.0 g, 7.25 mmol), palladium acetate (122 mg, 0.37 mmol), tricyclohexyl phosphine (210 mg, 0.75 mmol) and trimethylacetic acid (115 mg, 1.13 mmol) in N,N-dimethylacetamide (20 mL) was stirred for 6 hours at 100 C. The resulting mixture was cooled to room temperature and then filtered. The filtrate was concentrated under vacuum. The residue was purified by reverse phase chromatography (acetonitrile 0-55/0.05% sodium bicarbonate in water) to afford tert-butyl 3-(3-amino-8-chloro-7-fluoro-6-isoquinolyl)-6, 8-dihydro-5H-imidazo[1,2-a]pyrazine-7-carboxylate (500 mg, 1.20 mmol) as a yellow solid. LCMS (ESI) [M+H]+=418.1.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

To a mixture of compound V (49.8 g), DCM (500 mL) and DMF (5 mL) in a 500 mL three-neck flask, oxalyl chloride (38 g, 1.5 eq) was added at 0~10 C. The reaction mixture was warmed to RT. After completion of the reaction, the solvent was removed by concentration. DCM (200 mL) was added to obtain the compound VI solution in DCM. (0099) To a mixture of compound VII (30 g), DCM (240 mL) and TEA (6 eq) in a 1000 mL three-neck flask at 0~10 C, the solution of compound VI in DCM obtained from the above step was added dropwise, the reaction mixture was warmed to RT. After the reaction was completed, water (300 mL) was added to quench the reaction. The organic phase was washed with IN HCI aqueous solution (500 mL), saturated NaHC03 aqueous solution (500 mL) and water (500 mL). The organic phase was concentrated under vacuum. The crude product was recrystallized from IPAc/Heptane to afford compound VIII (61 g, 98% yield, 99.7% chiral purity).

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; WANG, Peng; LI, Pixu; GU, Xiangyong; GE, Yadong; WANG, Zhong; GAO, Feng; DU, Qiangqiang; (25 pag.)WO2019/90269; (2019); 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. 40155-43-9, name is 5-Aminopyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., category: Pyrazines

5-aminopyrazine-2-carboxylic acid (493 mg, 3.54 mmol; Ark Pharm, Inc., Libertyville, IL) was stirred in dry Lambda/,Lambda/-dimethylformamide (3.0 mL) at room temperature under nitrogen. Solid potassium carbonate (742 mg, 5.37 mmol) was added, followed by benzyl bromide (0.43 mL, 3.6 mmol). The mixture was stirred for 22 hours and then diluted with ethyl acetate and water. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was purified by silica chromatography using a 4Og pre-packed column, eluting with ethyl acetate. The product fractions were combined, evaporated, and dried under high vacuum to afford (I- 22a) (161 .2 mg, 0.70 mmol, 20%): m/z 229.9 (M+H)+.

The synthetic route of 40155-43-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/29461; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 113305-94-5, 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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Imidazo[1,2-a]pyrazine-6-carbonitrile (5-2) To a solution of 5-aminopyrazine-2-carbonitrile (5-1) (350 mg, 2.92 mmol) in ethanol (15 mL) was added 2-chloroacetaldehyde (4 mL, 40% in water). The mixture was stirred at 110 C. overnight. The solution was concentrated, then purified by chromatography on silica gel to afford the title compound (280 mg). MS (m/z): 145.1 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 5-Aminopyrazine-2-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; US2012/245178; (2012); 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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H11BrN2O3

Example 8 r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acid ethyl ester(3-Bromo-6-methyl-2-oxo-2H-pyrazin-1 -yl)-acetic acid ethyl ester was reacted with 2,2-difluoro-2-phenyl-ethylamine in the presence of a base, at elevated temperature, to yield the title compound as shown in the Scheme above. Table 5 below lists the reagent amounts, base and temperature combinations applied to this reaction, as well as yield.

The synthetic route of 221136-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 767340-03-4, 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. 767340-03-4, name is (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step C: Preparation of r2RV4-oxo-4-f3-(‘trifluoromethyl)-5.6-dihvdrori,2,41triazolor4.3- a1pyrazin-7(8H)-yl]-l -(2 A5-trifluorophenv0butan-2-amine (2-5) Into a 250 ml flask were charged chloro(l,5-cyclooctadiene)rhodium(I) dimer{[Rh(cod)Cl]2}(46 mg, 0.093 mmol) and (R,S) t-butyl Josiphos (106 mg, 0.196 mmol), ammonium chloride (12.5 mg, 0.234 mmol), and enamine amide (25 g, 61.8 mmol) under a nitrogen atmosphere. Degassed MeOH was then added (225 mL) and the mixture was stirred at room temperature for 1 h. The slurry was transferred into a hydrogenator under nitrogen. After degassing three times, the enamine amide was hydrogenated under 100 psi hydrogen gas at 50 0C for 18 h. Assay yield was determined by EtaPLC to be 97% and optical purity to be 94% ee.The optical purity was further enhanced in the following manner. The methanol solution from the hydrogenation reaction (18 g in 180 mL MeOH) was concentrated and switched to methyl t- butyl ether (MTBE) (45 mL). Into this solution was added aqueous Eta3PO4 solution (0.5 M, 95 mL). After separation of the layers, 3NNaOH (35 mL) was added to the water layer, which was then extracted EPO with MTBE (180 mL + 100 mL). The MTBE solution was concentrated and solvent switched to hot toluene (180 mL, about 75 0C). The hot toluene solution was then allowed to cool to 0 0C slowly (5 – 10 h). The crystals were isolated by filtration (98 – 99% ee); m.p. 114.1 – 115.7 0C. lH NMR (300 MHz, CD3CN): delta 7.26 (m), 7.08 (m), 4.90 (s), 4.89 (s), 4.14 (m), 3.95 (m), 3.40 (m), 2.68 (m), 2.49 (m), 1.40 (bs).Compound 2^5 exists as amide bond rotamers. Unless indicated, the major and minor rotamers are grouped together since the carbon- 13 signals are not well resolved:13C NMR (CD3CN): delta 171.8, 157.4 (ddd , JCF = 242.4, 9.2, 2.5 Hz), 152.2 (major), 151.8 (minor), 149.3(ddd; JCF = 246.7, 14.2, 12.9 Hz), 147.4 (ddd, JCF = 241.2, 12.3, 3.7 Hz), 144.2 (q, JCF = 38.8 Hz), 124.6 (ddd , JCF= 18.5, 5.9, 4.0 Hz), 120.4 (dd , JCF = 19.1, 6.2 Hz), 119.8 (q, JCF = 268.9 Hz), 106.2 (dd , JCF = 29.5, 20.9 Hz), 50.1, 44.8, 44.3 (minor), 43.2 (minor), 42.4, 41.6 (minor), 41.4, 39.6, 38.5 (minor), 36.9.

The synthetic route of (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/81151; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem