Tag: M.W=100-200

Related Products of 6705-33-5,Some common heterocyclic compound, 6705-33-5, name is Pyrazin-2-ylmethanol, molecular formula is C5H6N2O, 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 5 mL of diethyl ether was added 2-hydroxymethylpyrazine (100 mg, 0.9 mmol), stirred at room temperature, and 60% sodium hydride(80 mg, 2 mmol). After stirring was continued for 10 minutes, trichloroacetonitrile (202 mg, 1.4 mmol) was added,The reaction was complete after 2 hours by TLC. The residue was purified by column chromatography on a rotary evaporator (petroleum ether: ethyl acetate = 30: 1) to give 160 mg of product in 70% yield.

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

Reference:
Patent; Fudan University; Shao Liming; Xu Yulong; Chen Yiyi; Li Wei; Xie Qiong; (25 pag.)CN107151254; (2017); A;,
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Pyrazine | C4H4N2 – PubChem

Application of 19847-12-2,Some common heterocyclic compound, 19847-12-2, name is Pyrazinecarbonitrile, molecular formula is C5H3N3, 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 250 mL round-bottomed flask, pyrazine-2-carbonitrile (10 g, 95.1 mmol), pyridine (2.26 g, 2.33 ml, 28.5 mmol) and 2-mercaptopropionic acid (10.1 g, 95.1 mmol) were combined to give a light yellow solution. The reaction mixture was heated to 100 C. and stirred for 2 h. Upon cooling, the thick yellow mixture was diluted with 100 mL ethanol and stirred for 30 min. The slurry was then filtered, and washed with diethyl ether (2*100 mL) to give 5-methyl-2-pyrazin-2-yl-thiazol-4-ol (17.86 g, 97.1%) as yellow solid which was used directly without further purification. Trifluoro-methanesulfonic acid 5-methyl-2-pyrazin-2-yl-thiazol-4-yl ester:

The synthetic route of 19847-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Alam, Muzaffar; Bhagirath, Niala; Du Bois, Daisy Joe; Hawley, Ronald Charles; Minatti, Ana Elena; Kennedy-Smith, Joshua; Wilhelm, Robert Stephen; US2013/158040; (2013); A1;,
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Some common heterocyclic compound, 19847-12-2, name is Pyrazinecarbonitrile, molecular formula is C5H3N3, 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. Recommanded Product: 19847-12-2

To a solution of pyrazine-2-carbonitrile 13 (6.90 g, 65.65 mmol) in toluene (48 mL) and DMF (5 mL) was added sulfuryl chloride (21.2 mL, 260.8 mmol) over 10 min. The reaction mixture was stirred for 30 min in an ice bath, then allowed to warm up to room temperature gradually, after which it was stirred for 5 h. The toluene layer was decanted, and the reddish oil residue was extracted three times with diethyl ether. The combined toluene and ether layers were quenched with ice water and cooled in an ice bath. The combined layers were then neutralized with solid NaHCO3, then separated, and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered, and the solvent was evaporated under reduced pressure to afford the title compound. The crude product was purified by silica gel chromatography (eluent: 100% dichloromethane) to give 3-chloropyrazine-2-carbonitrile 14 as a white powder (4.7 g, 51%). Rf = 0.76 (dichloromethane); mp 44-46 C (lit. [14] : 47-48 C); IR (KBr) numax (cm-1): 3088 (nuCHar), 2242 (nuCN), 1377 (nuC=C), 1087 (nuC-N); 1H NMR (400 MHz, DMSO-d6): delta 8.91 (d, 1H, J = 2.4 Hz, H-6), 8.88 (d, 1H, J = 2.4 Hz, H-5); 13C NMR (100 MHz, DMSO-d6): delta 150.67 (C-3), 147.97 (C-5), 144.26 (C-6), 129.87 (C-2), 114.66 (CN); MS (ESI) m/z (%): 140.3 (100) [M + H]+, 142.3 (40) [M + H + 2]+. Anal. calcd for C5H2ClN3: C, 43.04; H, 1.44; N, 30.11. Found: C, 43.18; H, 1.45; N, 30.16.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19847-12-2, its application will become more common.

Reference:
Article; Loidreau, Yvonnick; Marchand, Pascal; Dubouilh-Benard, Carole; Nourrisson, Marie-Renee; Duflos, Muriel; Lozach, Olivier; Loaec, Nadege; Meijer, Laurent; Besson, Thierry; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 171 – 183;,
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Related Products of 1320266-90-7, The chemical industry reduces the impact on the environment during synthesis 1320266-90-7, name is 8-Chloro-3-isopropylimidazo[1,5-a]pyrazine, I believe this compound will play a more active role in future production and life.

To a solution of Intermediate 5-c (1.9 g, 9.7 mmol) in DMF cooled to 0C was slowly added a 0.7N solution of N-bromosuccinimide in DMF (15.2 ml, 10.7 mmol) under an atmosphere of nitrogen. After the addition was completed the reaction mixture was stirred for 15 minutes. Water was added; a precipitate formed, and was collected by filtration to provide Intermediate 5-e as a beige solid.

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, 8-Chloro-3-isopropylimidazo[1,5-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2015/74138; (2015); A1;,
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These common heterocyclic compound, 77112-53-9, name is Imidazo[1,2-a]pyrazine-2-carboxylic acid, 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. SDS of cas: 77112-53-9

General procedure: Imidazo[1,2-a]pyrazine-2-carboxylic acid (5) (1.0 equiv.) Mukaiyama?s reagent and 2-chloro-1-methylpyridinium iodide (1.2 equiv.) were suspended in DMF (5.0 mL) under nitrogen atmosphere. Into the reaction mixture, aliphatic/aromatic amines (6a-l) (1.0 equiv.) and 1-methylimidazole (2.0 equiv.) were added. A homogeneous solution was formed after a gentle stirring. The reaction mixture was sealed in a microwave glass reactor and then irradiated by microwave oven at a constant temperature of 80 C with continuous stirring (1 min ramp, 15 min reaction time). After the reaction was completed, the solvent was removed through a rotary evaporator and the resulting residue was extracted by a biphasic system of 45 mL diethyl ether and 45 mL water. After the layer separation, the ether layer was dried by anhydrous sodium sulphate, followed by an evaporation of ether to get compounds 7a-l (Scheme-I).

The synthetic route of Imidazo[1,2-a]pyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
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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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H7N3O2

In fitted with magnetic stirring and reflux condensation tube (with drying tail pipe) 250 ml three-necked bottle are respectively added with a 3 – amino pyrazine -2 – carboxylic acid methyl ester 15.4g (about 0.1 muM), 120 ml of concentrated ammonia water, stirring at room temperature under the condition of 10h, filtering, washing, 60 C drying, be 12.5g yellow solid that 3 – amino pyrazine -2 – formamide. Yield: 90.6

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Li Zhulai; (15 pag.)CN106699759; (2017); A;,
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Pyrazine | C4H4N2 – PubChem

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 13134-38-8 as follows. Computed Properties of C6H9N3

b. 2-(Chloromethyl)-5,8-dimethylimidazo[1,2-a]pyrazine To a solution of 3,6-dimethylpyrazin-2-amine (1.0 g, 8.1 mmol) in EtOH (20 mL) was added 1,3-dichloropropan-2-one (1.03 g, 8.1 mmol). The reaction mixture was stirred at reflux for 1 h. Then the solvent was removed. The product was purified by reverse column chromatography to give the title compound as a brown solid (570 mg, yield 85%). ESI MS: m/z 196 [M+H]+. 1H NMR (400 MHz, DMSO-d5): delta 8.10 (s, 1H), 7.65 (s, 1H), 4.94 (s, 2H), 2.70 (s, 3H), 2.54 (s, 3H).

According to the analysis of related databases, 13134-38-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sunovion Pharmaceuticals Inc.; US2012/178748; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 946493-27-2, These common heterocyclic compound, 946493-27-2, name is 3,5-Dimethylpyrazine-2-carboxylic acid, 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.

[0443] To a 4 mL scintillation vial equipped with a stir bar was charged 3,5-dimethylpyrazine- 2-carboxylic acid (23.4 mg, 0.167 mmol), DMF (0.5 mL), HATU (66.4 mg, 0.174 mmol) and DIPEA (0.08 mL, 0,455 mmol). The mixture was stirred for 5 minutes at ambient temperature and then a solution of 3-amino-4-(4-(2,4-difluorophenoxy)piperidin-l -yl)benzonitrile (50 rng, 0.152 mmol) in DMF (0.5 mL) was added in a single portion. The reaction mixture was stirred at 70C overnight, then cooled to ambient temperature, and diluted with water (2 mL). The mixture was sonicated and stirred until a residue was observed around the inside of the vessel. The liquids were decanted, leaving an oily residue to which was added MeOH (~1 mL). The mixture was heated until it became a translucent solution and was then sonicated and stirred at ambient temperature until a precipitate was observed. The material was filtered and the solids were washed with minimal MeOH, collected, and dried under vacuum to give the title compound as a white solid (25.7 mg, 37%). NMR (400 MHz, DMSO-ifc) delta ppm 1.88 – 2.02 (m, 2 H), 2.10 – 2.24 (m, 2 H), 2.59 (s, 3 H), 2.85 – 3.00 (m, 5 H), 3.10 – 3.22 (m, 2 H), 4,47 – 4.64(m, 1H), 6.97 – 7.09 (m, i H), 7,27 – 7,45 (m, 3 H), 7.60 (dd, J=8.34, 2.02 Hz, 1H), 8.55 (s. 1H), 8.70 (d,./ 1.77 Hz, 1H), 10.71 (s, 1H); ESI-MS m/z [M i l . 464.2,

The synthetic route of 946493-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
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Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-25-1, A common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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 30 2- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N-(5-METHYLSULFANYLMETHYL- PYRAZIN-2-YL)-PROPIONAMIDE [000205] A solution of methyl 5-chloropyrazine-2-carboxylate (5.00 g, 28.97 mmol) in acetonitrile (290 ML) was treated with a fresh bottle of silver (I) fluoride (11.00 g, 86.70 mmol). The reaction setup was covered with aluminum foil, and the reaction mixture was heated at reflux overnight. The mixture was filtered through a pad of celite, and the pad of celite was rinsed with acetonitrile. The filtrate was then concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 25% ethyl acetate/hexanes) afforded 5-fluoro-pyrazine-2-carboxylic acid methyl ester (2.98 g, 66%) an off-white solid upon cooling to 0C. An analytical sample was obtained by trituration with petroleum ether to afford 5-fluoro-pyrazine-2-carboxylic acid methyl ester as a white crystalline solid: mp 55.6-56. 7C, EI-HRMS m/e calcd for C6HSFN202 (M 156.0335, found 156.0331.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/52869; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, molecular formula is C6H6N2O, 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. HPLC of Formula: C6H6N2O

To a solution of N,N- bis(4-methoxybenzyl)ethanesulfonamide (Example 12.0, 73.13 g, 0.209 mol, 1.2 equiv.) in anhydrous THF (600 mL) at -78 C was added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equiv.) via additional funnel slowly, and the resulting mixture was stirred for 10 min. A solution of 5-methylpyrazine-2-carbaldehyde (Example 33.1, 21.3 g, 0.174 mol, 1.0 equiv.) in anhydrous THF (150 mL) was then added, and the resulting mixture was stirred at the same temperature for 45 min and allowed to warm to RT for 2 h. The reaction mixture was quenched by addition of an aqueous ammonium chloride solution (200 mL) and extracted with EtOAc (2 x 2 L). The combined organic layers were washed with brine (2 x 500 mL). After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford an oil. The oil thus obtained was purified by flash column chromatography (silica gel, 230-400 mesh) to afford the two isomers. The faster moving isomer (32 g as white solid) was obtained from the column with a gradient of 10 % to 30 % EtOAc in petroleum ether. 1H NMR (400 MHz, DMSO-d6) delta 8.61 (d, J = 1.5 Hz, 1H), 8.51 (d, J = 1.5 Hz, 1H), 7.22- 7.11 (m, 4H), 6.90- 6.80 (m, 4H), 6.10 (d, J = 5.9 Hz, 1H), 5.29 (dd, J = 5.9, 2.2 Hz, 1H), 4.36- 4.16 (m, 4H), 3.73 (m, 6H), 3.70-3.66 (m, 1H) 2.50 (merged with solvent peak, 3H) and 1.10 (d, J = 7.0 Hz, 3H). LCMS-ESI (pos.) m/z: 472.4 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50866-30-3, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
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Pyrazine | C4H4N2 – PubChem