Tag: M.W=100-200

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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Chloropyrazine-2-carboxylic acid

Step 1: 5-chloro-N-[l-(trifluoromethyl)cyclopropyl]pyrazine-2-carboxamideN,N-Diisopropylethylamine (1.3 niL, 7.5 mmol) was added to a mixture of 5- chloropyrazine-2-carboxylic acid (0.40 g, 2.5 mmol), N,N,N’,N’-tetramethyl-0-(7- azabenzotriazol-l-yl)uronium hexafluorophosphate (1.0 g, 2.8 mmol) and 1- (trifluoromethyl)cyclopropanamine (0.32 g, 2.5 mmol) (Oakwood, Cat.No.: 038175) in dichloromethylene (10 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was worked up with saturated aqueous NaHCCh, and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-20%) to afford the desired product (0.41 g, 67%). LCMS (M+H) +: m/z = 266.0/267.9.

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; INCYTE CORPORATION; YAO, Wenqing; BURNS, David M.; ZHUO, Jincong; WO2012/177606; (2012); A1;,
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Application of 313339-92-3,Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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 solution of 3,5-dichloropyrazine-2-carbonitrile (100 mg, 0.578 mmol), phenylboronic acid (0.635 mmol, 77.5 mg, 1.1 equiv), [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.029 mmol, 5 mol%) in degassed dioxane/water 4:1 (6 mL) was sodium carbonate (0.635 mmol, 1.1 equiv) and the reaction mixture was stirred for 4h under nitrogen at 100oC. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and aqueous layer was extracted twice with EtOAc, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give product: ESI-MS (m/z): 215.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloropyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford; ANTCZAK, Monika; READY, Joseph; ZHANG, Youngyou; (332 pag.)WO2018/218251; (2018); A1;,
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Related Products of 274-79-3, These common heterocyclic compound, 274-79-3, name is Imidazo[1,2-a]pyrazine, 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.

Imidazo[1 ,2-a]pyrazine(l1 ) (4.38 g, 36.8 mmol) was dissolved in methanol (100 mL) and hydrogenated at 1 atm/25 0C hydrogen over platinum(IV) oxide (0.522 g, 1.838 mmol) for 24 h. The catalyst was filtered and the filtrate concentrated to afford afford product in 4.8 g that was used without further purification. LC/MS = 124 (M+H)+, retention time = 0.34 minutes (2 minute method (high pH)).

The synthetic route of 274-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); A1;,
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Reference of 98-97-5,Some common heterocyclic compound, 98-97-5, name is Pyrazine-2-carboxylic acid, molecular formula is C5H4N2O2, 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.

Diphenyl phosphorylazide (8.6 g) was added dropwise to a solution of pyrazine-2- carboxylic acid (3 g) in THF (30 ml) and TEA (9 ml) and the resulting reaction mixture was stirred at RT for 2 hours. On completion, THF was removed under reduced pressure to give a residue, which was further purified by column chromatography (SiO2, gradient 10-40 % EtOAc/n-hexane) yielding the desired product (2.5g, 70%).

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

Reference:
Patent; SENTINEL ONCOLOGY LIMITED; WO2007/144579; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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: 3,5-Dichloropyrazine-2-carbonitrile

j1416] Compound 356 from above was dissolved in 10 mE DMF. To it were added 3,5-dichloropyrazine-2-cabonitrile (250 mg, 1.42 mmol) and DIEA (500 IL, 2.84 mmol). The mixture was stirred at RT for 2 hours, diluted with 150 mE EtOAc, washed with water x3, dried, concentrated in vacuo, and subjected to silica flash column using 0 to 3% MeOR in DCM to isolate 3-chloro-54(2R,3R)-2-methyl-3-(3-methyl- 2-oxoimidazolidin-1 -yl)piperidin-1 -yl)pyrazine-2-carboni- trile (357, 200 mg, 42% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 313339-92-3, its application will become more common.

Reference:
Patent; JIA, Zhaozhong J.; CHEN, Wei; THOMAS, William D.; US2015/158865; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 356783-26-1, 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. 356783-26-1, name is Methyl 3,6-difluoropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE II-2 In 3.0 mL of N,N-dimethylformamide was dissolved 0.3 g of methyl 3,6-difluoro-2-pyrazinecarboxylate. After adding 0.16 g of sodium acetate at an ice-cooled temperature, the mixture thus obtained was stirred at 50 C. for 2.5 hours. The reaction mixture was poured into a mixture of 50 mL of ethyl acetate and 30 mL of water, and the organic layer was separated. The remaining aqueous phase was extracted with three 25 mL portions of ethyl acetate. The organic layers were united, washed successively with 15 mL of water and 15 ml of saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=1:2] to obtain 0.03 g of methyl 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxylate as a colorless solid product.

The chemical industry reduces the impact on the environment during synthesis Methyl 3,6-difluoropyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); A1;,
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Related Products of 4774-10-1,Some common heterocyclic compound, 4774-10-1, name is 3-Methoxypyrazin-2-amine, molecular formula is C5H7N3O, 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 procedure similar to Example 59 (Method B), Parts A and B was used, except that 3-(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 420.8 (MH+). 1H NMR (400 MHz, METHANOL-d4) delta ppm 1.04-1.21 (m, 2H) 1.36-1.63 (m, 5H) 1.70-1.91 (m, 4H) 2.30-2.44 (m, 1H) 2.44-2.55 (m, 1H) 2.82-2.98 (m, 1H) 3.20-3.29 (m, 1H) 3.51 (dd, J=14.02, 4.42 Hz, 1H) 3.59-3.86 (m, 1H) 3.96 (td, J=9.47, 4.80 Hz, 1H) 4.03 (s, 3H) 4.79-4.87 (m, 1H) 7.79-7.94 (m, 2.7H) 8.26 (s, 0.3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxypyrazin-2-amine, its application will become more common.

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;,
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Electric Literature of 43029-19-2,Some common heterocyclic compound, 43029-19-2, name is 3-Aminopyrazin-2(1H)-one, molecular formula is C4H5N3O, 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 solution of 3-aminopyrazin-2-ol (209.35 mg, 1.88 mmol, 1 eq) in DMF (5 mL) was added NaH (82.90 mg, 2.07 mmol, 60% purity, 1.1 eq) at 0C,then the reaction was stirred at 0C for 15 mins then a solution of tert-butyl 5-fluoro-2- (methylsulfonyloxymethyl)indole-1-carboxylate (647 mg, 1.88 mmol, 1 eq) in DMF(10 mL) was dropwised into it , the reaction was stirred at 20C for 12 hr. The reaction was diluted with water (50 mL).The mixture was extracted with ethyl acetate (50 mL*2). The organic phase was washed with brine (50 mL*2) ,dried over anhydrous Na2SO4, filtered and concentrated in vacuum to give a residue. The residue was purified by columnchromatography to give tert-butyl 2-[(3-amino-2-oxo-pyrazin-1-yl)methyl]-5-fluoro-indole-1- carboxylate (I-341) (350 mg, 52% yield) as a yellow solid.1H NMR (400 MHz, CDCl3) d 1.67 (s, 9 H) 5.42 (s, 2 H) 5.48 ( s, 2 H) 6.25 (s, 1 H) 6.58 (d, J=4.63 Hz, 1 H) 6.83 (d, J=4.63 Hz, 1 H) 7.01 (td, J=9.15, 2.65 Hz, 1 H) 7.11 (dd, J=8.60, 2.43 Hz, 1 H) 8.03 (dd, J=9.04, 4.63 Hz, 1 H).

The synthetic route of 43029-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SITARI PHARMA, INC.; CAMPBELL, David; CHAPMAN, Justin; CHEUNG, Mui, H.; DIRAIMONDO, Thoams, R.; DURON, Sergio, G.; (615 pag.)WO2020/33784; (2020); 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. 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Safety of 5-Chloropyrazine-2-carbonitrile

The 5-chloropyrazine-2-carbonitrile (0.034 mL, 0.368 mmol), rac- I -((2S,3R,4R)-4-amino-2- cyclopropyl-6-(3,6-dihyd ro-2H-pyran-4-yl)-3-methyl-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for a preparation see Intermediate 78, 60 mg, 0.184 mmol), DIPEA (0.096 mL, 0.551 mmol) and Nmethyl-2-pyrrolidone (NMP) (2 mL) were irradiated in a microwave at 200 C for I h. The reactionwas purified directly using a MDAP (Formic) to give a brown solid. This solid was eluted through a NH2 SPE (5 g) using MeOH, the eluent was concentrated and dried to give the product (34 mg, 0.079 mmol, 43.1%) as a brown solid. LCMS (2 mm Formic): Rt = 0.98 mi [MH] = 430.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
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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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., Product Details of 56423-63-3

To a reaction flask were added compound 28 (100 mg, 0.189 mmol), 2-bromopyrazine (50 mg, 0.27 mmol), Pd(dppf)Cl2 (5 mg, 0.006 mmol) and sodium carbonate (60 mg, 0.558 mmol), 5 mL glycol dimethyl ether and 0.9 mL water were added, bubbled with nitrogen gas for 10 minutes, and the reaction was heated to 100 C in microwave and reacted for half an hour. After TLC detected the reaction was complete, the reaction was concentrated, purified by silica gel column chromatography to afford 41 mg of a product, yield: 45.3%. LC-MS(APCI): m/z = 480.3 (M+1)+. 1H NMR (400 MHz, CDCl3) delta 8.68 (s, 2H), 8.58 (s, 1H), 8.52 (s, 1H), 8.30 (s, 1H), 8.03 (s, 1H), 7.68 (d, J = 8.9 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 4.91 (d, J = 50.6 Hz, 1H), 4.35 (s, 1H), 3.68 (dd, J = 36.4, 23.2 Hz, 2H), 3.37 – 3.28 (m, 1H), 3.15 (d, J = 12.4 Hz, 1H).

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; Shenzhen Targetrx, Inc.; WANG, Yihan; ZHAO, Jiuyang; AL, Yixin; (55 pag.)EP3553056; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem