Month: September 2021

6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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. Formula: C6H6BrN3O2

Step 1 : 3-amino-6-bromo-N-methylpyrazine-2-carboxamide[00261] Methyl 3-amino-6-bromo-pyrazine-2-carboxylate (7.5 g, 32.32 mmol) was suspended in 40% aqueous methylamine and the resulting mixture stirred vigorously at RT for 4 hours. The resultant precipitate was collected, washed with water and dried to give the desired product(6.73g, 90% Yield). IH NMR (400.0MHz, DMSO) d 2.76 (s, 3H), 7.75 (br s, 2H), 8.34 (s, IH),8.58 (b rs, IH) ppm; MS (ES+) 232.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1196152-38-1, A common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, molecular formula is C5H2BrF3N2, 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 81N- (3,4-Dif [uoropheny[)-3-methy[-5-{[5- (trif[uoromethy[)pyrazin-2-y[]amino- 1 ,2-thiazo[e-4-carboxamide A mixture of 5-amino-N-(3,4-dif[uoropheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide [Intermediate 3] (100 mg, 0.37 mmo[, 1.0 eq), 2-bromo-5-(trif[uoromethy[)- pyrazine [CAS-RN: 1196152-38-1] (105 mg, 0.45 mmo[, 1.2 eq) and cesiumcarbonate (242 mg, 0.74 mmo[, 2.0 eq) in 4.0 mL dioxane/DMF (7/1) was p[aced ina microwave via[ that was f[ushed with argon. Then, pa[[adium(II) acetate (8 mg,0.04 mmo[, 0.1 eq) and Xantphos (21 mg, 0.04 mmo[, 0.1 eq) were added.Afterwards, the via[ was sea[ed and the reaction mixture was stirred at anenvironmenta[ temperature of 110 C for 4 h. On coo[ing, the reaction mixture was partitioned between ethy[ acetate and water. The organic phase was washed with brine and the phases were separated by the use of a Whatman fi[ter. The vo[ati[e components of the organic phase were removed in vacuo. Purification was conducted via preparative HPLC (Method A) to give 36 mg (22 % yie[d of theory) ofthe tit[e compound.UPLC-MS (Method 1): Rt = 1.36 mm; MS (ESIneg) m/z = 414 [M-H].1HNMR (400 MHz, DMSO-d6): oe [ppm] = 2.46 (s, 3H), 7.34-7.54 (m, 2H), 7.95 (dd, 1H), 8.82 (s, 1H), 8.91 (s, 1H), 10.53 (s, 1H), 11.46 (s, 1H).

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 16298-03-6, 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 16298-03-6 as follows.

Step 1a: Methyl 3-[(2,4-dimethoxybenzyl)amino]pyrazine-2-carboxylate Sodium triacetoxyborohydride (7.82 g, 36.89 mmol) was added to a mixture of methyl 3-aminopyrazine-2-carboxylate (4.00 g, 26.12 mmol) and 2,4-dimethoxybenzaldehyde (4.83 g, 29.04 mmol) in 1,2-dichloroethane (90 ml). The reaction was continued at room temperature for 24 hours. Sodium triacetoxyborohydride (13.0 g, 61.34 mmol) and 2,4-dimethoxybenzaldehyde (8.0 g, 48.14 mmol) were added and the reaction continued at room temperature over night. Water and DCM were added and the phases separated. The product was purified further by flash chromatography (SiO2, heptane:ethyl acetate, product came at 50percent ethyl acetate) and recrystallisation (DCM/heptane) to give a slightly yellow solid (5.00 g, 63percent). 1H NMR (400 MHz, CDCl3) delta 8.35-8.27 (br, 1H), 8.22 (d, 1H), 7.82 (d, 1H), 7.20 (d, 1H), 6.48-6.43 (m, 1H), 6.43-6.37 (m, 1H), 4.63 (d, 2H), 3.93 (s, 3H), 3.84 (s, 3H), 3.77 (s, 3H). MS m/z 304 (M+H)+.

According to the analysis of related databases, 16298-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheng, Leifeng; Jonforsen, Maria; Schell, Peter; US2009/88439; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 109838-85-9, These common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, 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.

(S)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)(4-(trifluoromethyl)phenyl)methanol: To a mixture of (R)-2,5-dihydro-3,6-dimethoxy-2- isopropylpyrazine (5.2 tnL, 29 mmol)(commercially available from 3B Scientific Corporation Product List (Order Number 3B3-054672)) and THF (50 mL) at -78°C was added n-butyllithium (2.5 M solution in hexane, 12 mL, 31 mmol). The mixture was stirred for 15 minutes. The colorless solution turned light brown. A solution of 4- (trifluoromethyl)benzaldehyde (5.1 mL, 38 mmol)(commerciaHy available from 3B Scientific Corporation Product List (Order Number 3B4-3644)) in THF (50 mL) was added dropwise through a dropping funnel at -78°C. The mixture was stirred for 1 hour. The reaction mixture was diluted with EtOAc and washed with a mixed solution of aqueous Na2HPO4 and KH2PO4 solution (pH =8). The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The crude residue was separated into two isomers by silica gel chromatography: 0-2percent- 10percent CH3CN-CH2CI2. The product was obtained as light yellow oil (2.3 g, 22 percent). LCMS (API-ES) m/z: 359 (M+H*).

The synthetic route of 109838-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/11871; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-29-5, Name is 2-Amino-5-chloropyrazine, 33332-29-5, 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.

Step A: S,S-Dimethyl-N-(5-chloropyrazin-2-yl)sulfilimine (5) Compound 5 is prepared from 2-amino-5-chloropyrazine as described above for 2 in Example 1A to afford pure 5 as a smelly, tan solid, m.p. 119-120.

Statistics shows that 2-Amino-5-chloropyrazine is playing an increasingly important role. we look forward to future research findings about 33332-29-5.

Reference:
Patent; Merck & Co., Inc.; US4609659; (1986); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 54608-52-5, 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 54608-52-5 as follows.

Ethyl 1-benzyl-2,4-dioxopiperidine-3-carboxylate (58.5 mg, 0.21 mmol) in EtOH (2 mL) was added to a biotage microwave vial under nitrogen containing 2-hydrazinopyrazine (38.5 mg, 0.35 mmol) at RT. To this stirred reaction mixture was added AcOH (0.024 mL, 0.42 mmol) and then stirred at RT for 18 hours in a sealed microwave vial. The reaction was heated to 140 C for 10 hours in the microwave reactor and cooled to RT. The reaction mixture was evaporated in the Genevac and then redissolved in 2 ml DMSO, filtered and the crude product was purified by flash RP chromatography (35g Puriflash, 15mu, HC column), using decreasingly polar mixtures of water (containing 1% NH4OH) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 5-benzyl-2-(pyrazin-2-yl)-1,2,6,7-tetrahydro-3H-pyrazolo[4,3-c]pyridine-3,4(5H)-dione (14.6 mg, 19.2 %) as a white solid.

According to the analysis of related databases, 54608-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fairley, Gary; Greenwood, Ryan; McMillan, Caroline Anne; Tetrahedron Letters; vol. 59; 39; (2018); p. 3574 – 3578;,
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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6863-74-7

Reference Example 104 2-Cyano-6-methylthiopyrazine A mixture of 2-chloro-6-cyanopyrazine (1.40 g, 10.0 mmol), sodium thiomethoxide (0.78 g, 11.0 mmol) and THF (100 ml) was refluxed for 2 hrs.. The reaction mixture was combined with ethyl acetate and water.. The organic layer was washed with saturated brine and dried over magnesium sulfate.. The solvent was evaporated to give the titled compound (1.25 g, 83 %) as pale yellow crystals.1H-NMR (CDCl3) delta: 2.61 (3H, s), 8.49 (1H, s), 8.60 (1H, s). IR(KBr): 2241, 1670, 1521, 1390, 1190, 1167, 1138, 1108, 887, 734 cm-1.

According to the analysis of related databases, 6863-74-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1424336; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3, A common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, molecular formula is C4H3BrClN3, 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-Bromo-5-chloropyrazin-2-amine (200 mg, 0.96 mmol),Triethylamine (290 mg, 2.88 mmol), cuprous iodide(5mg, 0.33mmol)And bis(triphenylphosphine)palladium dichloride (13 mg, 0.02 mmol) was dissolved in tetrahydrofuran (5 mL).The reaction solution was stirred at room temperature.Then trimethylethynyl silicon (0.15 mL, 1.06 mmol)Slowly adding dropwise to the above reaction solution,After completion of the dropwise addition, the resulting reaction solution was heated to 55 C to continue the reaction for 1 hour.After the reaction system is cooled to room temperature,The reaction solution was diluted with ethyl acetate (50 mL).Filter and concentrate the filtrate under reduced pressure.The residue obtained was purified by silica gel column chromatography (PE/EA (v/v) = 30/1).The title compound was obtained as a pale yellow solid ( 208 g, 96%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; Nie Biao; Xu Juan; Yan Huan; Chen Jianping; (90 pag.)CN108727369; (2018); A;,
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. 32111-21-0, name is 2-Iodopyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H3IN2

To a solution of 3-nitrophenol (0.151 g, 0.733 mmol) in DMSO (5 mL) was added NaH (35 mg of a 60% dispersion, 0.88 mmol) at 0 C under Ar atmosphere. After stirring for 30 min, 2-iodopyrazine (0.133 mg, 0.953 mmol) was added and mixture heated to 85 C for 4h. To the mixture was added satd. NH4Cl solution (25 mL) and the product extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to yield a crude residue which was purified by column chromatography to afford (97 mg, 61% yield) 2-(3-nitrophenoxy)pyrazine as a white solid.

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; DECIPHERA PHARMACEUTICALS, LLC; WO2006/71940; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-28-4,Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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.

[0504] Compound 481A was prepared by an analogous method as that of 473B, except using compound 2-chloro-6-aminopyrazine in place of compound 2-bromo-6-aminopyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-chloropyrazine, its application will become more common.

Reference:
Patent; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem