Category: 113305-94-5

Reference of 113305-94-5, These common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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.

Reflux a solution of 2.24 g (18.65 mmol) of 5-aminopyrazine-2-carbonitrile and 9.45 mL (74.40 mmol) of boron trifluoride etherate in 50 mL of methanol for 2 h. Concentrate the reaction mixture under reduced pressure and take up the residue obtained in 200 mL of EtOAc and 10 mL of a saturated aqueous solution of NaHCO3. Dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluding with a cyclohexane/EtOAc 1:1 mixture. After concentration under reduced pressure, we obtain 1.4 g of methyl 5-aminopyrazine-2-carboxylate in the form of oil. Yield=49%

Statistics shows that 5-Aminopyrazine-2-carbonitrile is playing an increasingly important role. we look forward to future research findings about 113305-94-5.

Reference:
Patent; Sanofi Aventis; US2009/318473; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 113305-94-5,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.

A 5 liter flange-neck flask equipped with an air stirrer rod and paddle,thennometer, water condenser and nitrogen bubbler is charged with sodium hydride (22.4 g, 560.1 mmol) and anhydrous THF (3 L). To the well stirred mixture is added 2-amino- 5-cyanopyrazine (67.0 g, 557.8 mmol) portion-wise over 1.5 hours while allowing for any foaming. The internal temperature remains at 22 C throughout. The mixture is stirred for 35 minutes. Then I -(2-methoxy-6-4-methoxy-benzyloxy)-phenyi)-3,3-bis-methyisulfanyl-propenone (146.0 g, 373.9 mmoi) is added at 22 C over one hour. The yellow suspension is stirred for 45 minutes at room temperature and then heating is applied until the reaction is at a gentle refiux. Afier 19 hours at 65 C the reaction mixture is cooled to 15 C. The mixture is then split in two halves and each lot is quenched into water (2 L) and extracted with ethyl acetate (2 x L). The organic extractsare combined and washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure at 40 C to give the title compound (196 g, 100% crude) as a yellow/orange solid which is used in the next step without further purification. LC-ES/MS mIz 463.2 [M¡ÂHf.

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

Reference:
Patent; ELI LILLY AND COMPANY; STANCATO, Louis Frank; (58 pag.)WO2017/15124; (2017); 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 113305-94-5, 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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a stirred mixture of 5-aminopyrazine-2-carbonitrile (542 mg, 4.5 mmol) in THF (20 mL) was slowly added sodium hydride (240 mg, 6.02 mmol) below 15 C. The resulting mixture was stirred at room temperature for 1 hour and compound 106 (1 .0 g, 3.01 mmol) was added. The reaction mixture was stirred at 60 C for 4 hours, quenched with ice-water and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound 107 (1.0 g, crude) as a yellow solid, which was used for the next step without further purification.

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

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

113305-94-5, Adding some certain compound to certain chemical reactions, such as: 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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 113305-94-5.

Synthesis 2C (R)-tert-Butyl 2-((2-(5-cyanopyrazin-2-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)methyl)morpholine-4-carboxylate (R)-tert-Butyl 2-((2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)methyl)morpholine-4- carboxylate (1.44 g, 3.64 mmol), 2-amino-5-cyanopyrazine (0.612 g, 5.09 mmol, 1.4 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.267 g, 0.291 mmol, 0.08 eq.), rac-2,2′- bis(diphenylphosphino)-1 ,1 ‘-binaphthyl (0.362 g, 0.582 mmol, 0.16 eq.) and caesium carbonate (2.37 g, 7.28 mmol) were suspended in anhydrous dioxane (33 ml_) under argon. Argon was bubbled through the mixture for 30 minutes, after which the mixture was heated to 100C for 22 hours. The reaction mixture was cooled and diluted with dichloromethane, then absorbed on to silica gel. The pre-absorbed silica gel was added to a 100 g KP-Sil SNAP column which was eluted with 20-50% ethyl acetate in hexanes to give the partially purified product as an orange gum. The crude product was dissolved in dichloromethane and purified by column chromatography on a 90 g SingleStep Thomson column, eluting with 20% ethyl acetate in dichloromethane, to give the title compound (1.19 g, 68%). H NMR (500 MHz, CDCI3) delta 1.50 (9H, s), 2.71-2.88 (1 H, m), 2.93-3.08 (1 H, m), 3.27- 3.32 (1 H, m), 3.40-3.44 (1 H, m), 3.55-3.64 (1 H, m), 3.71-3.77 (1 H, m), 3.82-4.11 (3H, m), 5.33 (1 H, broad s), 7.19 (1 H, s), 8.23 (1 H, s), 8.58 (1 H, s), 8.84 (1 H, s). LC-MS (Agilent 4 min) Rt 2.93 min;m/z (ESI) 480 [MH+].

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 113305-94-5.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; COLLINS, Ian; MATTHEWS, Thomas Peter; FARIA DA FONSECA MCHARDY, Tatiana; OSBORNE, James; LAINCHBURY, Michael; WALTON, Michael Ian; GARRETT, Michelle Dawn; WO2013/171470; (2013); 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. 113305-94-5

EXAMPLE 1E N-(2-{[tert-butyl(dimethyl)silyl]oxy}-5-chlorophenyl)-N’-(5-cyano-2-pyrazinyl)urea A mixture of Example 1B (0.84 g, 7 mmol) and Example 1D (2.0 g, 7.06 mmol) in toluene (20 mL) was heated to reflux for 48 hours, cooled to room temperature, and filtered. The filter cake was washed with hexanes (2*10 mL) to provide 1.66 g (58.5%) of the desired product. MS (ESI(-)) m/z 402 (M-H)-; 1H NMR (500 MHz, DMSO-d6) delta 10.99 (s, 1H), 9.33 (s, 1H), 9.00 (d, J=1.3 Hz, 1H), 8.82 (d, J=1.36 Hz, 1H), 8.07 (d, J=2.7 Hz, 1H), 7.07 (dd, J=2.7 and 8.8 Hz, 1H), 6.97 (d, J=2.71 Hz, 1H), 0.98 (s, 9H), 0.32 (s, 6H).

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; Li, Goaquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/34038; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

113305-94-5, The chemical industry reduces the impact on the environment during synthesis 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

To a stirred mixture of 5-aminopyrazine-2-carbonitrile (131 mg, 1.09 mmol) in THF (8 mL) was slowly added sodium hydride (73 mg, 1.82 mmol) below 15 C. The resulting mixture was stirred at room temperature for 1 hour and compound 207 (302 mg, 0.91 mmol) was added. The reaction mixture was then stirred at 60 C for 4 hours, quenched with ice-water, and extracted with ethyl acetate. The organic layer was dried over Na2504 and concentrated to afford the title compound 208 (280 mg, crude) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 113305-94-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); 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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., 113305-94-5

Synthesis 1C (S)-tert-Butyl 2-((2-(5-cyanopyrazin-2-ylamino)-5-(trifluoromethyl)pyridin-4-carboxylate S)-tert-Butyl 2-((2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)methyl)morpholine-4- carboxylate (4.67 g, 1 1.8 mmol), 2-amino-5-cyanopyrazine (1.98 g, 16.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.86 g, 0.94 mmol), rac-2,2′- bis(diphenylphosphino)-1 ,1 ‘-binaphthyl (0.54 g, 0.87 mmol) and caesium carbonate (7.69 g, 23.6 mmol) were suspended in anhydrous dioxane (108 ml_) under argon. Argon was bubbled through the mixture for 30 minutes, after which the suspension was heated to 100C for 29 hours. The reaction mixture was cooled and diluted with dichloromethane, then absorbed onto silica gel. The pre-absorbed silica gel was added to a 340 g KP-Sil SNAP column which had been equilibrated with 20% ethyl acetate in hexane. Column chromatography, eluting with a gradient of 20-35% ethyl acetate in hexane, gave partially purified material as an orange gum. This was further purified by column chromatography, eluting with 20% ethyl acetate in dichloromethane, to give the title compound as a light tan powder (3.28 g, 58%). H NMR (500 MHz, CDCI3) delta 1.49 (9H, s), 2.73-2.86 (1 H, m), 2.94-3.07 (1 H, m), 3.26- 3.31 (1 H, m), 3.38-3.43 (1 H, m), 3.57-3.61 (1 H, m), 3.70-3.75 (1 H, m), 3.83-4.08 (3H, m), 5.31 (1 H, broad s), 7.12 (1 H, s), 8.13 (1 H, s), 8.23 (1 H, s), 8.57 (1 H, s), 8.87 (1 H, s). LC- MS (Agilent 4 min) Rt 2.90 min; m/z (ESI) 480 [MH+].

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; CANCER RESEARCH TECHNOLOGY LIMITED; COLLINS, Ian; MATTHEWS, Thomas Peter; FARIA DA FONSECA MCHARDY, Tatiana; OSBORNE, James; LAINCHBURY, Michael; WALTON, Michael Ian; GARRETT, Michelle Dawn; WO2013/171470; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 113305-94-5

To 2-amino-5-cyanopyrazine (Ark Pharm Inc) (4.87 g, 40.5 mmol) and hydroxylamine hydrochloride (6.20 g, 89 mmol) in EtOH (30 mL) was added triethylamine (9.44 g, 93 mmol). The reaction was stirred at 80C for 1 h. The precipitate was filtered, washed with a small volume ethano and dried on high vacuum to give 5-amino-N’-hydroxypyrazine-2- carboximidamide (5.9 g, 38.5 mmol, 95% yield) as a yellow powder. HPLC RT = 0.593 min (Method A), ESIMS [M+H]+ = 154

Statistics shows that 113305-94-5 is playing an increasingly important role. we look forward to future research findings about 5-Aminopyrazine-2-carbonitrile.

Reference:
Patent; NOVARTIS AG; HEBACH, Christina; KALLEN, Joerg; NOZULAK, Joachim; TINTELNOT-BLOMLEY, Marina; WIDLER, Leo; WO2013/80120; (2013); 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. 113305-94-5

Svnthesis 1-1 -B5-(4-(4~Methoxybenzylamino)-5-nitropyridin-2-ylamino)pyrazine-2-carbonitrile A mixture of palladium (II) acetate (38 mg, 0.17 mmol) and (+/-)-2,2″- bis(diphenylphosphino)-1 ,1″-binaphthalene (318 mg, 0.51 mmol) a mixture of toluene and DMF (1 :1, 10 ml_) was degassed under a stream of nitrogen gas with stirring for 30 minutes. After addition of 2-amino-5-cyanopyrazine (245 mg, 2.04 mmol), sodium tert- butoxide (196 mg, 2.04 mmol) and N-(4-methoxybenzyl)-2-bromo-5-nitropyridin-4-amine (575 mg, 1.70 mmol), the mixture was degassed for a further 5 minutes and then heated at 140C for 30 minutes in a microwave reactor. Upon cooling, the mixture was diluted with methanol and isolated by SPE using 3 x 2.5 g MP-TsOH cartridges, washing with methanol and then eluting with 2 M ammonia in methanol. The basic fractions were concentrated in vacuo to give the title compound (470 mg, 1.25 mmol, 73%) which was used without further purification. LCMS (2) Rt = 2.18min; m/z (ESI-) 376 (M-H); (ESI+) 378 (MH+).

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