Category: 50866-30-3

Related Products of 50866-30-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 50866-30-3 name is 5-Methylpyrazine-2-carbaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

155. ( +)-2-( (3,4-trans)-4-methyl- 1-( ( 5-methylpyrazin-2- yl)methyl)pyrrolidin-3-yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- f] ri,2,41triazin-4(3H)-one [1114] To a stirred solution of (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (150 mg, 0.49 mmol) in MeOH (10 mL) was added 5-methylpyrazine-2-carbaldehyde (72 mg, 0.59 mmol) at room temperature and stirred for 2 h under argon atmosphere. To the resulting solution was added NaCNBH3 (93 mg, 1.48 mmol) and stirring was continued for another 8 h at room temperature. The volatiles were evaporated under reduced pressure. The residue was diluted with water and extracted with CH2C12 (2 x 20 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-4-methyl-l-((5- methylpyrazin-2-yl)methyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4- yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (54 mg, 27%) as an off-white solid; 1H- NMR (DMSO-de, 400 MHz): delta 8.54 (s, 1H), 8.47 (s, 1H), 7.64 (s, 1H), 3.96-3.94 (m, 2H), 3.88-3.83 (m, 2H), 3.52-3.47 (m, 2H), 3.41-3.37 (m, 1H), 2.99-2.95 (m, 2H), 2.91-2.85 (m, 2H), 1.67-1.62 (m, 1H), 2.47 (s, 3H), 2.34-2.31 (m, 1H), 1.88-1.82 (m, 4H), 1.12 (d, 3H); Mass (ESI): 410 [M++l]; LC-MS: 98.17%; 410 (M++l); (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 1.86 min. 0.05% TFA in water: ACN; 0.8 ml/min); UPLC (purity): 98.35%; (column; Acquity BEH C-18, 50×2.1 mm, 1.7mu; RT 1.16 min. 0.025% TFA (Aq): ACN; 0.50 ml/min; Chiral HPLC: 98.63%, R, = 9.76 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) 0.1% DEA in n-Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D20: + 68.65 (c = 0.25, DCM). TLC: 5% MeOH/DCM (Rf: 0.4).

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

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 50866-30-3, 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. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(1R,2S)-1-Hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methylpyrazin-2-yl)propane-2-sulfonamide and (1S,2R)-1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methylpyrazin-2-yl)propane-2-sulfonamide, Example 27.2 (1063) To a solution of N,N-bis(4-methoxybenzyl)ethanesulfonamide (Example 12.0, 73.13 g, 0.209 mol, 1.2 equivalent.) in anhydrous THF (600 mL) at -78 C. was slowly added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equivalent.) via additional funnel, and the resulting mixture was stirred for 10 min. Next, a solution of 5-methylpyrazine-2-carbaldehyde (Example 27.1, 21.3 g, 0.174 mol, 1.0 equivalent.) in anhydrous THF (150 mL) was added, and the mixture was stirred at the same temperature for 45 min and then allowed to warm to RT for 2 h. The reaction mixture was then quenched by addition of aqueous ammonium chloride (200 mL) and extracted with EtOAc (2¡Á2 L). The combined organic layers were washed with brine (2¡Á500 mL). No product was observed in the ammonium chloride or brine layers. After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford the product as an oil. The product thus obtained was purified by flash column chromatography (silica gel, 230-400 mesh) to afford the two isomers. The faster moving isomer (32 g) was obtained as a white solid 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 (app s, 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 positive ion) m/z: 472.4 (M+H)+. (1S,2S)-1-Hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methyl-pyrazin-2-yl)propane-2-sulfonamide and (1R,2R)-1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methyl-pyrazin-2-yl)propane-2-sulfonamide, Example 28.3 (1064) Further elution of the mixture in Example 27.2 with a gradient of 30% to 35% 21 EtOAc in 201 petroleum ether yielded Example 27.3 (16 g, pale yellow gummy liquid). 1H NMR (400 MHz, CDCl3) delta 8.62 (d, J=1.6 Hz, 1H), 8.44 (d, J=1.5 Hz, 1H), 7.25-7.12 (m, 4H), 6.93-6.82 (m, 4H), 5.17 (d, J=7.1 Hz, 1H), 4.47 (d, J=15.2 Hz, 3H), 4.14 (d, J=15.4 Hz, 2H), 3.82 (s, 3H), 3.82 (s, 3H), 3.66-3.61 (m, 1H), 2.60 (d, J=2.0 Hz, 3H), and 1.08 (dd, J=7.2, 2.1 Hz, 3H). LCMS (ESI positive ion) m/z: 472.4 (M+H)+.

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

Reference:
Patent; AMGEN INC.; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEDLEY, Simon J.; HOUZE, Jonathan; JUDD, Ted C.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YEH, Wen-Chen; (415 pag.)US2017/320860; (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. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, A new synthetic method of this compound is introduced below., Product Details of 50866-30-3

A vial was charged with C65 (100 mg, 0.33 mmol), and the vial was evacuated and flushed with nitrogen; this procedure was repeated twice, tetrahydrofuran (1.6 mL) was added, and the solution was cooled to -78 C. 2,2,6,6-Tetramethylpiperidinylmagnesium chloride, lithium chloride complex (1 M solution in tetrahydrofuran and toluene; 0.497 mL, 0.497 mmol) was added, and the reaction mixture was allowed to stir for 1 hour at -78 C. In a separate vial, 5-methylpyrazine-2- carbaldehyde (80.9 mg, 0.662 mmol) was dissolved in tetrahydrofuran (1.6 mL), and the resulting solution was cooled in a dry ice/acetone bath for 10 minutes. This solution wasthen added to the reaction mixture, which was subsequently allowed to stir while slowly warming to 15 C. After 1 hour, it was combined with two similar reaction mixtures derived from C65 (50 mg, 0.17 mmol; 100 mg, 0.33 mmol), and the resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 15 mL). The combined organic layers were concentrated in vacuo and subjected to reversed-phaseHPLC (Column: Phenomenex Synergi Max-RP, 10 pm; Mobile phase A: 0.1% trifluoroacetic acid in water; Mobile phase B: acetonitrile; Gradient: 15% to 45% B), affording a diastereomeric mixture of 14 and 15 as a viscous, brick-red oil. Combined yield of diastereomeric mixture: 180 mg, 0.425 mmol, 51%. This material was separated into its component diastereomers via supercritical fluid chromatography [Column: Regis Technologies, (S,S)-Whelk-O 1, 10 pm; Mobile phase: 3:2 carbon dioxide I (ethanol containing 0.1 % ammonium hydroxide)]. The firsteluting diastereomer, obtained as a light yellow solid, was designated as 14. Yield: 58.6mg, 0.138 mmol, 32% for the separation. LCMS m/z 423.9 (chlorine isotope pattern observed) [M+H]. 1H NMR (400 MHz, CD3OD) 9.12 (br s, 1 H), 8.92 (5, 1 H), 8.83-8.74 (brs, 1H), 8.48 (5, 1H), 8.18 (d, J=9.0 Hz, 1H), 7.74 (dd, J=9.0, 2.0 Hz, 1H), 6.51 (5, 1 H), 5.58-5.46 (m, 1 H), 4.29 (dd, J=1 1.8, 5.3 Hz, 1 H), 3.80-3.66 (br m, 1 H), 3.66-3.52 (br m, 1H), 2.79-2.66 (m, 1H), 2.60 (5, 3H), 2.42-2.27 (br m, 1H), 2.13-2.00 (br m, 1H),1.77-1.63 (brm, 1H), 1.28 (brd, J=5.5 Hz, 3H).The second-eluting diastereomer, also isolated as a light yellow solid, was designated as 15. Yield: 56.8 mg, 0.134 mmol, 32% for the separation. LCMS m/z 423.9 (chlorine isotope pattern observed) [M+H]. 1H NMR (400 MHz, CD3OD) 9.12 (br s, 1 H), 8.92 (5, 1 H), 8.82-8.74 (br s, 1 H), 8.47 (br s, 1 H), 8.18 (d, J=8.5 Hz, 1 H),7.74 (dd, J=9.0, 2.0 Hz, 1H), 6.50 (5, 1H), 5.57-5.46 (m, 1H), 4.21 (dd, J=11.8, 4.8 Hz,1 H), 3.82-3.70 (br m, 1 H), 3.62-3.47 (br m, 1 H), 2.71-2.57 (br m, 1 H), 2.59 (5, 3H),2.48-2.35 (m, 1H), 2.24-2.13(brm, 1H), 1.63-1.50 (brm, 1H), 1.34(d, J=6.0 Hz, 3H).

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; PFIZER INC.; BRODNEY, Michael Aaron; CHAPPIE, Thomas Allen; CHEN, Jinshan Michael; COE, Jotham Wadsworth; COFFMAN, Karen Jean; GALATSIS, Paul; GARNSEY, Michelle Renee; HELAL, Christopher John; HENDERSON, Jaclyn Louise; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G.; MARTINEZ-ALSINA, Luis Angel; PETTERSSON, Martin Youngjin; REESE, Matthew Richard; ROSE, Colin Richard; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; WARMUS, Joseph Scott; ZHANG, Yuan; (193 pag.)WO2018/163066; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

50866-30-3, Name is 5-Methylpyrazine-2-carbaldehyde, 50866-30-3, 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.

The compound (82.2 mg) obtained in Example 47-3 was dissolved in methanol (5.0 ml) and added with the compound (35.9 mg) obtained in Example 73-1, followed by the addition of sodium cyanoborohydride (36.9 mg). Then, the reaction solution was adjusted to about pH 5 with acetic acid, followed by stirring at room temperature for 16 hours. The reaction solution was added with a saturated aqueous sodium bicarbonate solution and then extracted with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off. The resulting crude product was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (84.0 mg) of the subject compound as a pale-yellow solid. MS(FAB,Pos.):m/z=526[M+H]+1H-NMR(500MHz,DMSO-d6):delta=0.87(6H,t,J=7.3Hz),1.69-1.78(4H,m),2.47(3H,s),2.86-2.95(4H,m),3.82(2H,s),3.85(2H,s),4.11(2H,s),4.26(2H,d,J=5.2H z),7.58-7.62(6H,m),7.88-7.89(2H,d,J=8.7Hz),7.95-7.96(2H,d,J=8.4Hz),8.47(1H,dd,J=0.6,1.3Hz),8.69(1H,d,J=1.4Hz ),10.47(1H,s),10.70(1H,brs),14.51(1H,brs).

Statistics shows that 5-Methylpyrazine-2-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 50866-30-3.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem