Tag: M.W=100-200

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

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. COA of Formula: C5H6N2O

Triphenylphosphine(7.80 g, 29.7 mmol) and phthalimide (4.50 g, 30.6 mmol)were added to a solution of crude 2-(hydroxylmethyl)pyrazine(2.80 g, 25.5 mmol) in dry tetrahydrofuran (200 mL).The stirred solution was then cooled in an ice bath beforediisopropyl azodicarboxylate (5.90 g, 30.4 mmol) wasslowly added over 5 min. The solution was stirred for twodays at room temperature and taken to dryness underreduced pressure and the resulting yellow oil was suspendedin ethanol (20 mL) before again being taken todryness under reduced pressure, producing a thick yellowslurry. The slurry was dissolved in hot ethanol (~200 mL)and left to cool and evaporate to ~50 mL overnight atroom temperature. The resulting solid was filtered off togive the desired product as an analytically pure slightlyyellow solid (3.82 g, 75%). Found: C, 65.14; H, 3.89; N, 17.52.Calc. for C13H9N3O2: C, 65.27; H, 3.79; N, 17.56. 1H NMR (300MHz, CDCl3): delta (ppm) 8.66 (s, 1H, H-3), 8.48 (s, 2H, H-2 +H-1), 7.89-7.92 (m, 2H, phth-H), 7.77-7.74 (m, 2H, phth-H),5.06 (s, 2H, CH2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6705-33-5, its application will become more common.

Reference:
Article; Feltham, Humphrey L. C.; Cowan, Matthew G.; Kitchen, Jonathan A.; Jameson, Guy N. L.; Brooker, Sally; Supramolecular Chemistry; vol. 30; 4; (2018); p. 296 – 304;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 109838-85-9,Some common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, molecular formula is C9H16N2O2, 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.

R8 (212 g, 1151 mmol) in tetrahydrofuran (dry) (600 mL) is cooled to ?78¡ã C. Then n-butyllithium (2.5 M in hexanes, 552 mL, 1381 mmol) is added dropwise, keeping the temperature below ?78¡ã C. After 30 min R9 (324 g, 1209 mmol) in tertahydrofuran (dry) (120 mL) is added dropwise. The reaction mixture is stirred at ?78¡ã C. for 1 h. The mixture is quenched with saturated NH4Cl solution and extracted three times with ethyl acetate. The organic layer is washed with brine, dried over Na2S04 and evaporated in vacuo. The residue is purified by flash chromatography (heptane/ethyl acetate=80/20). Yield 60percent

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
Pyrazine – Wikipedia,
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 69214-33-1 as follows. Formula: C6H4ClN3

Morpholine (2.0 ml, 23.2 mmol) was added to a stirred solution of a mixture 72/28 of 3-bromo-8-chloro-imidazo[l,2-a]pyrazine and 3,8-dibromo-imidazo[l,2-a]pyrazine (intermediate 15) (5.9 g, 11.6 mmol) and DIPEA (1.93 ml, 13.9 mmol) in ACN (54 ml). The mixture was stirred at 80 C for 7 h. and then the solvent was evaporated in vacuo. The crude product was dissolved in DCM and washed with a saturated solution of sodium carbonate. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 10/90). The desired fractions were collected and evaporated in vacuo and the crude product precipitated from Et20 to yield intermediate 26 (2.79 g, 85%) as a white solid.

According to the analysis of related databases, 69214-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; PASTOR-FERNANDEZ, Joaquin; VAN GOOL, Michiel, Luc, Maria; MARTIN-MARTIN, Maria, Luz; VANHOOF, Greta, Constantia, Peter; WO2011/110545; (2011); 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. 14508-49-7, name is 2-Chloropyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C4H3ClN2

Preparation of compound 46: To a solution of 2-chloropyrazine (500 mg, 0.0027 moles, 1 eq) in DMF (20 ml) was added cesium carbonate (1.7 g, 0.0052 moles, 2 eq) followed by N-Boc-piperazine (506.8 mg, 0.0027 moles, 1.0 eq). The reaction mixture was heated at 100 C. for 12 hrs and monitored by TLC. Upon completion, the excess solvent was removed under reduced pressure and the crude material was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. The crude material was washed, purified on silica gel (60-120 mesh) using 30% ethylacetate-hexane to provide 400 mg of compound 46 (44.1% yield).

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; Salituro, Francesco G.; Saunders, Jeffrey O.; Yan, Shunqi; US2010/331307; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, belongs to Pyrazines compound, 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 63286-28-2, Recommanded Product: 2-Chloro-3-hydrazinylpyrazine

[00118] To a 0 0C solution of l-(4-chlorophenyl)cyclobutanecarboxylic acid (105.3 mg, 0.50 mmol) in THF (2 mL) was added 4-methylmorpholine (60.5 muL, 0.55 mmol). The reaction mixture was stirred for 10 minutes, and then isobutyl chloroformate (67.4 muL, 0.52 mmol) was added dropwise over a 2 minute period. Upon completion of addition, the reaction mixture was stirred for 1 h. A solution of Compound IA (72.3 mg, 0.50 mmol) in THF (3 mL) was then added dropwise over a 2 minute period. The resulting mixture was stirred for 10 minutes and then the cooling bath was removed. The reaction mixture was allowed to warm to room temperature where it stirred for 1 h. After this time, water (5 mL) and ethyl acetate (10 mL) were added, and the resulting mixture was stirred for 10 minutes. At the conclusion of this period, the organic phase was separated, dried over Na2SO4, and then concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, 0-60% ethyl acetate / hexanes) to afford compound 2A, which was used directly in the preparation of compound 2B set forth below. LC/MS (m/z) = 337 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-3-hydrazinylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/130951; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 186534-02-1,Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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 1 Synthesis of TBN (FIG. 2) 2-[[(1,1-Dimethylethyl)oxidoimino]methyl]-3,5,6-trimethylpyrazine (TBN). To aldehyde 5 (1.9 g, 0.013 mol) in methanol (200 mL) was added tert-butylhydroxylamine (1 g, 0.011 mol), and the solution was refluxed for 2 h. Another portion of tert-butyl hydroxylamine (1 g, 0.011 mol) was then added, and the solution refluxed until aldehyde 5 was completely reacted. Solvent was removed in vacuo, and the product was extracted. The solution was dried with Na2SO4, and solvent removed in vacuo. The product was purified by column chromatography, eluding with ethyl acetate/petroleum ether (1/1, v/v), to produce TBN as a light yellow solid (1.1 g, 38% yield), mp: 68-70 C. 1H NMR (CDCl3, ppm): 7.82 (s, 1H), 2.47 (s, 3H), 2.50 (s, 3H), 2.52 (s, 3H), 1.63 (s, 9H). ESI-MS: 222 [M+H]+, 244 [M+Na]+. Anal. (C12H19N3O) C, H, N.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Yuqiang; Jiang, Jie; Yu, Pei; Sun, Yewei; Wang, Linda; Zhang, Zaijun; US2011/34485; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 19745-07-4, 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. 19745-07-4, name is 2,5-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Example 745-[(5-Ch[oropyrazin-2-y[)amino]-N- (3,4-dif[uoropheny[)-3-methy[- 1 ,2-thiazo[e-4- carboxamideA mixture of 5-amino-N-(3,4-dif[uoropheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide [Intermediate 3] (300 mg, 1.11 mmo[, 1.0 eq), 2,5-dich[oropyrazine [CAS RN:19745-07-4] (166 mg, 1.11 mmo[, 1.0 eq) and cesium carbonate (835 mg,2.56 mmo[, 2.3 eq) in 11 mL dioxane/DMF (7/1) was p[aced in a microwave via[ and f[ushed with argon. Then, pa[[adium(II) acetate (25 mg, 0.11 mmo[, 0.1 eq) andXantphos (64 mg, 0.11 mmo[, 0.1 eq) were added. The via[ was capped and the reaction mixture was stirred at an environmenta[ temperature of 110 ¡ãC overnight. On coo[ing, the reaction mixture was partitioned between dich[oromethane/methano[ (5/1) and water. The organic phase was washed with brine and the phases were separated by the use of a Whatman fi[ter. The crude materia[ wascrysta[[ized with dich[oromethane/methano[ and the preciptitate was iso[ated via fi[tration. After drying, 192 mg (6 percent yie[d of theory) of the tit[e compound were obtained.UPLC-MS (Method 3): Rt = 1 .29 mm; MS (ESIneg) m/z = 380 [M-H].1HNMR (400 MHz, DMSO-d6): oe [ppm] = 2.44 (s, 3H), 7.38-7.53 (m, 2H), 7.94 (dd,1H), 8.56 (s, 2H), 10.47 (s br, 1H), 11.10 (s br, 1H).

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

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

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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C6H7N3O2

(A) Methyl 2-bromo-3-pyrazine carboxylate To a stirred mixture of 12.7 g. of methyl 2-amino pyrazine carboxylate and 47 ml. of 48percent hydrobromic acid there was added, dropwise, 12.6 ml. of bromine keeping the temperature at 0¡ã. A solution of 14.4 g. of sodium nitrite in 60 ml. of water was then added, dropwise, at 0¡ã and the reaction mixture stirred for 15 minutes. The reaction mixture was basified to pH 8 with sodium bicarbonate and extracted with ethyl acetate and again with chloroform. The organic layers were dried over magnesium sulfate, filtered and concentrated to a yellow oil. Recrystallization from ether-hexane yielded the product, m.p. 43¡ã-45¡ã C.

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; Schering Corporation; US4632923; (1986); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6164-79-0, name is Methyl 2-pyrazinecarboxylate, belongs to Pyrazines compound, 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 6164-79-0, Formula: C6H6N2O2

To a mixture of NaH (60% in mineral oil, 0.68 g, 28.2 mmol),methyl pyrazine-2-carboxylate (3 g, 21.7 mmol) and dry DMF(30 mL), methyl acetate (2.09 g, 28.2 mmol) was added dropwiseunder N2 atmosphere. After being stirred at rt for 5 h, the reactionmixture was concentrated in vacuo, and the residue treated withsaturated aqueous NaHCO3 solution followed by extraction withEtOAc. The combined organic phase were dried with MgSO4,filtered, and concentrated in vacuo. Column chromatographicpurification (n-hexane/EtOAc = 8:1) yielded 5a as white solid(1.95 g, 50%). 1H NMR (CDCl3, 400 MHz) d keto form: 9.28 (d, 1H,J = 1.5 Hz), 8.80 (d, 1H, J = 2.4 Hz), 8.66 (overlapped, 1H), 4.18 (s,2H), 3.74 (s, 3H); enol form: 12.30 (s, 1H), 9.15 (d, 1H, J = 1.5 Hz),8.66 (overlapped, 1H), 8.60 (dd, 1H, J = 2.3, 1.5 Hz), 6.34 (s, 1H),3.85 (s, 3H).

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, Methyl 2-pyrazinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lee, Young Hun; Lee, Jung Min; Kim, Sang Geon; Lee, Yong Sup; Bioorganic and Medicinal Chemistry; vol. 24; 12; (2016); p. 2843 – 2851;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem