Month: January 2021

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. 54608-52-5, name is 2-Hydrazinopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. name: 2-Hydrazinopyrazine

A solution of 2-hydrazinopyrazine (1.10 g) in trifluoroacetic anhydride (10 mL) was stirred at room temperature for 4 h. To the mixture was added PPA (12 mL). The reaction mixture was heated at 80 C. for another 15 h. The reaction mixture was cooled to room temperature and filtered to afford the title compound as a white solid (0.94 g, 50.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 189.0 (M+1); 1H NMR (400 MHz, CDCl3) delta: 8.64 (s, 3H).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 56423-63-3, name is 2-Bromopyrazine, 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 56423-63-3, Formula: C4H3BrN2

General procedure: These compounds were synthesized according to previously reported method.3 Under nitrogen atmosphere, to a mixture of 25 (3.0 mmol), K2CO3 (4.5 mmol) and CuI (0.3 mmol) in DMA (10 mL) was added 24a-24c (3.0 mmol). The reaction flask was heated to 90 C and stirred for 36-48 h. After being cooled to rt, the reaction mixture was diluted with ethyl acetate and water. Under cooling with ice/water, concentrated HCl was added to adjust the pH to 3. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to yield the desired compounds 26a-26c.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Xu, Yulong; Yang, Xicheng; Chen, Yiyi; Chen, Hao; Sun, Huijiao; Li, Wei; Xie, Qiong; Yu, Linqian; Shao, Liming; Bioorganic and Medicinal Chemistry Letters; vol. 28; 12; (2018); p. 2148 – 2152;,
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. 6905-47-1, name is 2-Amino-6-methoxypyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H7N3O

A procedure similar to Example 59 (Method B), Parts A and B was used, except that 6-(methyloxy)-2-pyrazinamine (52.4 mg, 0.419 mmol) was used instead of 4-pyrimidinamine to add to the reaction mixture in Part A, to provide the Title compound. MS (ES+) m/z 420.9 (MH+). 1H NMR (400 MHz, METHANOL-d4) delta ppm 1.07-1.24 (m, 2H) 1.34-1.45 (m, 1H) 1.47-1.68 (m, 4H) 1.70-1.97 (m, 4H) 2.14-2.29 (m, 1H) 2.46-2.61 (m, 1H) 2.84-2.99 (m, 1H) 3.19-3.29 (m, 1H) 3.50 (dd, J=14.02, 4.42 Hz, 1H) 3.61-3.81 (m, 1H) 3.86-4.01 (m, 4H) 4.72 (q, J=7.49 Hz, 1H) 7.86 (s, 0.7H) 7.88-7.94 (m, 1H) 8.26 (s, 0.3H) 8.89 (s, 1H)

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 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;; ; Patent; GlaxoSmithKline Intellectual Property (No. 2) Limited; 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.; US8901119; (2014); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89464-87-9, name is 3-Methoxy-5-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 89464-87-9, Formula: C6H9N3O

3-methoxy-5-methylpyrazin-2-amine (0.33 g) and the product of Example 1, step (a) were subjected to the procedure described in Example 1, step (b) to afford the product as a pale yellow solid (0.68 g).m/e 389 (M+l)+, 100%.JH NMR (CDC13) 8 7.8 (1H, br), 7.58 (1H, br), 4.01 (3H, s), 2.35 (3H, s).MP 146-147C.Elemental Analysis:Theory: C 30.90, H 2.07, N 10.81 %Found: C 31.12, H 2.00, N 10.79 %

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-5-methylpyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2004/108717; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 313339-92-3, A common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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-Dichloropyrazine-2-carbonitrile (Example 12, Step 2, 31.0 g, 178.18 mmol) was dissolved in anhydrous diethyl ether (890 mL, 0.2M) and cooled to -78 C. Then MeMgBr in diethyl ether (3.0 M, 65.33 mL, 190.0 mmol) was added slowly to maintain low temperature. After the addition was complete, the mixture was slowly warmed room temperature and stirred 1 h. The mixture was poured into a beaker containing a mixture of HCl in water (1.0 M, 1 L) and ice (1 kg). The mixture was stirred vigorously for 10 min. The mixture was extracted with diethyl ether (3*1 L), the combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford the title compound as an orange oil (34 g, 99% yield). The mixture was used for the next reaction without further purification.

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLX Bio, Inc.; Beck, Hilary Plake; Biannic, Berenger; Bui, Minna Hue Thanh; Hu, Dennis X.; Jackson, Jeffrey J.; Ketcham, John Michael; Powers, Jay Patrick; Reilly, Maureen Kay; Robles-Resendiz, Omar; Shunatona, Hunter Paul; Walker, James Ross; Wustrow, David Juergen; Younai, Ashkaan; Zibinsky, Mikhail; (339 pag.)US2018/72743; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 399-66-6, 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. 399-66-6, name is [1,2,4]Triazolo[1,5-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Stage 4. Platinum (IV) oxide (2.75 g, 12.1 mmole) was added to a suspension, saturated with nitrogen, of CaO (9.30 g, 166 mmole) and [ 1, 2 , 4 ] -triazolo [ 1, 5-a] pyrazine (18.1 g, 151 mmole) in methoxyethanol (150 ml) . The reaction mixture was stirred for 21.5 hours under a hydrogen atmosphere. The catalyst was filtered off through filter earth and washed with DCM/ethanol (9:1). The filtrate was concentrated, and the solvent was removed firstly with toluene and then with 2-propanol. The residue was taken up in ethyl acetate, filtered again through filter earth, washed with ethyl acetate, and concentrated. The residue was washed with hot 2-propanol and concentrated in vacuo.

The chemical industry reduces the impact on the environment during synthesis [1,2,4]Triazolo[1,5-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; WO2009/90055; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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 875781-43-4, Formula: C6H4BrN3

Step 1To a partial suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g, 25.2 mmol) in 1,4- dioxane (100 mL) was added 2.0 M aqueous NaOH (25 mL, 50.0 mmol) and 37% aqueous formaldehyde (19 mL, 252 mmol). The dark homogenous reaction mixture was stirred at room temperature overnight. The organics were evaporated under reduced pressure. The aqueous layer was neutralized with 1.0 M HC1 and extracted with EtOAc (2x). The combined organics were concentrated to afford 2.6 g of an orange solid. Upon standing, a thick brown precipitate formed in the aqueous layer. The precipitate was collected by filtration and dried. The brown solid was extracted with hot 10% MeOH/EtOAc (3 x 200 mL). The extracts were combined and evaporated to provide an additional 3.05 g of orange solid. Overall yield was 5.65 g (87%) of (2-bromo-7-hydroxymethyl-pyrrolo[2,3-b]pyrazin- 5-yl)-methanol.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HENDRICKS, Robert Than; HERMANN, Johannes Cornelius; KONDRU, Rama K.; LOU, Yan; LYNCH, Stephen M.; OWENS, Timothy D.; SOTH, Michael; YEE, Calvin Wesley; WO2011/144584; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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. Computed Properties of C5H4N4

[0120] 5-chloro-2-methoxybenzoic acid (370.0 mg, 1.981 mmol) was dissolved in THF (10.0 mL), followed by the addition of catalytic amount of DMF (20 .iL) and oxalyl chloride (0.20 mL, 2.377 mmol) respectively. The reaction was allowed to stir at rt for 30 mm, concentrated in vacuo, and the residue was re-dissolved in THF (10.0 mL). In another flask, 5-aminopyrazine-2- carbonitrile (170.0 mg, 1.415 mmol) was dissolved in THF (5.0 mL) followed by addition of NaH (85.0 mg, 2.123 mmol, 60% in mineral oil). The mixture was stirred for 10 minutes before it was added to the flask containing the freshly prepared acid chloride dropwise at rt. The reaction was stirred at rt for 30 mm before silica gel was added to quench the reaction. Solvent was evaporated and the resulting residue was purified via silica gel column chromatography to yield 5-chloro-N-(5-cyanopyrazin-2-yl)-2-methoxybenzamide (40.0 mg, 10% yield) which was mixed with pyridinium chloride (550.0 mg). The mixture was heated to 200 C, stirred for 10 minutes and cooled down to rt. The resulting solid was dissolved in water and extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified via silica gel column chromatography to yield 5-chloro-N-(5-cyanopyrazin-2-yl)-2-hydroxybenzamide 3 (27.5 mg, 72% yield). ?H NMR (300 MHz, Acetone-d6) 6 9.70 (d, J= 1.5 Hz, 1H), 8.90 (d, J= 1.5 Hz, 1H), 8.16 (d, J= 2.7 Hz, 1H), 7.59 – 7.51 (m, 1H), 7.17 (d, J= 8.8 Hz, 1H). MS (ESI) exact mass calculated for [M+H] (C12H8C1N402) requires m/z 275.0, found m/z 275.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 113305-94-5, its application will become more common.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; JIN, Shengkan; AUGERI, David, J.; KIMBALL, David, S.; LIU, Peng; TAO, Hanlin; ZENG, Xiangang; (82 pag.)WO2016/81599; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 63286-28-2, The chemical industry reduces the impact on the environment during synthesis 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, I believe this compound will play a more active role in future production and life.

2-Chloro-3-hydrazinylpyrazine C-1 (15.6 g; 108 mmol) is slurried up in (300 ml) THF and cooled down in an ice bath to -5 C. Trifluoroacetic anhydride (17 ml; 118 mmol) is also dissolved in 300 ml THF and dropped slowly to the first solution. After 1 h most of the THF is evaporated, than a small amount of water is added and the mixture is extracted with DCM. The organic phase is dried over MgSO4 and evaporated to dryness. Yield: 100% HPLC-MS: (M+H)+=241/243; tRet=1.31 min; method FSUN2

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-Chloro-3-hydrazinylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENGELHARDT, Harald; US2015/133447; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 767340-03-4, The chemical industry reduces the impact on the environment during synthesis 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, I believe this compound will play a more active role in future production and life.

Into a 500 ml flask were charged chloro(1,5-cyclooctadiene)rhodium(I) dimer {[Rh(cod)Cl]2}(292 mg, 1.18 mmol) and (R,S) t-butyl Josiphos (708 mg, 1.3 mmol) under a nitrogen atmosphere. Degassed MeOH was then added (200 mL) and the mixture was stirred at room temperature for 1 h. Into a 4 L hydrogenator was charged the enamine amide 24 (118 g, 0.29 mol) along with MeOH (1 L). The slurry was degassed. The catalyst solution was then transferred to the hydrogenator under nitrogen. After degassing three times, the enamine amide was hydrogenated under 200 psi hydrogen gas at 50 C. for 13 h. Assay yield was determined by HPLC to be 93% 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 H3PO4 solution (0.5 M, 95 mL). After separation of the layers, 3N NaOH (35 mL) was added to the water layer, which was then extracted with MTBE (180 mL+100 mL). The MTBE solution was concentrated and solvent switched to hot toluene (180 mL, about 75 C). The hot toluene solution was then allowed to cool to 0 C. slowly (5-10 h). The crystals were isolated by filtration (13 g, yield 72%, 98-99% ee); m.p. 114.1-115.7 C. 1H NMR (300 MHz, CD3CN): delta7.26 (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): delta171.8, 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.

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, (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, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Thornberry, Nancy A.; Kaufman, Keith D.; US2006/270722; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem