Month: January 2021

Adding a certain compound to certain chemical reactions, such as: 58139-04-1, name is 2-Iodo-3-methoxypyrazine, 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 58139-04-1, Product Details of 58139-04-1

To a solution of 2-iodo-3-methoxypyrazine (22)9 (118 mg, 0.5 mmol) in THF (1 mL) was added isopropylmagnesium chloride (0.3 mL, 0.6 mmol, 2 M in THF) at 0 C. The mixture was stirred for exactly 7 min and a solution of 1,1?-bisindole-3,3?-dicarbaldehyde (14) (29 mg, 0.1 mmol) in THF (1 mL) was added dropwise. The reaction mixture was warmed to room temperature for 18 h and diluted with ethyl acetate (15 mL). The organic solution was washed with water (10 mL) and NH4Cl (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography using n-hexanes/ethyl acetate (1:1) as eluent to give diol 16 as a yellow oil (51 mg, 0.098 mmol, 98%) and an inconsequential mixture of diastereomers, which was used immediately in the next step. To a solution of 16 (51 mg, 0.098 mmol) in dichloromethane/acetonitrile (1:2, 5 mL) were added triethylsilane (28 mg, 38.4 muL, 0.24 mmol) and boron trifluoride diethyl etherate (34 mg, 29.6 muL, 0.24 mmol) at 0 C. The reaction mixture was stirred at 0 C for an additional 30 min and diluted with dichloromethane (15 mL). The solution was washed with NaHCO3 (satd, 10 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash column chromatography using ethyl acetate/methanol (19:1) as eluent to give the title compound as a yellow oil (40 mg, 0.084 mmol, 86%); numax (neat)/cm-1 3054, 2947, 2925, 2865, 1540, 1450, 1391, 1310, 1123, 1009, 740; deltaH (400 MHz, CDCl3) 8.05 (2H, d, J 2.8, 2¡ÁArH), 7.96 (2H, d, J 2.8, 2¡ÁArH), 7.77 (2H, d, J 7.4, 2¡ÁArH), 7.19-7.12 (4H, m, 4¡ÁArH), 7.18 (2H, s, 2¡ÁArH), 6.82 (2H, d, J 7.8, 2¡ÁArH), 4.31 (4H, d, J 4.2, 2¡ÁCH2), 3.99 (6H, s, 2¡ÁMe); deltaC (100 MHz, CDCl3) 158.8 (2¡ÁC), 146.1 (2¡ÁC), 138.9 (2¡ÁCH), 137.3 (2¡ÁC), 135.9 (2¡ÁCH), 126.6 (2¡ÁC), 126.3 (2¡ÁC), 123.3 (2¡ÁCH), 120.9 (2¡ÁCH), 119.9 (2¡ÁCH), 112.2 (2¡ÁC), 109.2 (2¡ÁCH), 53.7 (2¡ÁMe), 28.9 (2¡ÁCH2); m/z (ESI) 499 (65%, [M+Na]+), 376 (15), 311 (12), 261 (100); HRMS (ESI, [M+Na]+) found 499.1858. [C28H24N6NaO2]+ requires 499.1853.

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

Reference:
Article; Wang, Christy; Sperry, Jonathan; Tetrahedron; vol. 70; 21; (2014); p. 3430 – 3439;,
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

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

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

Application of 25710-18-3,Some common heterocyclic compound, 25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, molecular formula is C7H3Cl2N3, 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 suspension of 2,3-dichloro-pyrido[2,3-b]pyrazine (200mg; lmmol; leq), ethane sulfonamide (109.1 mg, 1 mmol, 1 eq.), 7-methyl-l,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene. hi (862 mg, 2.5 mmol, 2.5 eq.) and NaI (149.87 mg, lmmol, 1 eq.) in DMA (5 ml) is heated at 1000C in the microwave for 1 hour under high absorbance. HCl in dioxane (374.9 mul, 4M; 1.5 mmol, 1.5 eq.) then 3,5-dimethoxyaniline (765.8 mg, 5 mmol, 5 eq.) are added, and the resulting reaction mixture is heated at 1700C in the microwave for 30 min. The polymer is filtered off, washed with DMA, and the solvent evaporated under reduced pressure. The product was extracted withEtOAc, the organic layer is washed with brine and dried under MgSO4 them conecentrated to near dryness. The residue is purified by preparative HPLC to afford 69.4 mg (18 percent) of the title EPO compound as a parent. The parent (58.6 mg, 0.15 mmol, 1 eq.) is suspended in water (2 ml) then potassium hydroxide (300.9 mul, 0.50 M, 0.15 mmol, 1 eq.) is added and the mixture is lyophilised to afford 64 mg (99 percent) of the title compound as a yellow powder. IH NMR (DMSO- d6) delta 8.92 (s, IH), 8.34 (dd, J = 4.5, 1.7 Hz, IH), 7.79 (dd, J = 7.9, 1.7 Hz, IH), 7.31 (d, J = 2.3 Hz, 2H), 7.14 (dd, J = 7.9, 4.5 Hz, IH), 6.16 (t, J = 2.3 Hz, IH), 3.78 (s, 6H), 3.40 (q, J = 7.5 Hz, 2H), 1.15 (t, J = 7.5 Hz, 3H). HPLC (max plot) 99percent; Rt 2.87 min. LC/MS: (ES+): 390.3, (ES-): 388.3.

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

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/23186; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 297172-19-1, These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-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.

In 0 C lower, to the 5, 6, 7, 8-tetrahydro-imidazo [1, 5-a] pyrazine (50.0 mg, 0 . 40mmol) and Boc-(R)-3-amino-4-(2, 5-difluorophenyl) butanoic acid (128.0 mg, 0 . 40mmol) in dichloromethane (5 ml) is added in solution HOBT (54.5 mg, 0 . 42mmol). The reaction in the 0 C lower stirring 10 min, then adding EDC (96.6 mg, 0 . 50mmol). After removing the ice bath, the reaction stirring at ambient temperature 14h. The mixture is concentrated and used for purifying HPLC (Gilson; YMC-PackProC18 column, 100x20mmI. D. ; A solvent gradient from 10% acetonitrile, 90% water and 0.1% trifluoroacetic acid to 90% acetonitrile, 10% water and 0.1% trifluoroacetic acid), to obtain 103 mg in the form of a solid as the title compound.

Statistics shows that 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 297172-19-1.

Reference:
Patent; CGene Tech (Suzhou,China)Co.,Ltd; YU, QIANG; WEI, FENGPING; (31 pag.)CN101899047; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 117719-17-2, 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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Preparation of Intermediate I-03. A mixture of intermediate I-02 (360 mg, 1.35 mmol), indazole-4-boronic acid hydrochloride (600 mg, 2.97 mmol), K2CO3 (2 mL of saturated solution), PdCl2(dppf).DCM (112 mg, 0.135 mmol) in DME (5 mL) was heated under microwave irradiation for 10 min at 130 C. The reaction mixture was filtered through a celite pad, washing with DCM. The filtrate was dried over Na2SO4 and concentrated. The crude was purified by flash column chromatography (Isolute Si II 10 g cartridge) eluting with a gradient of DCM/MeOH (from 100% to 90:10) to yield 250 mg of the intermediate I-03 pure (Y: 62%).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-3-morpholinopyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); 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. 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone, A new synthetic method of this compound is introduced below., Computed Properties of C8H10N2O

General procedure: The ligands L1-L4 were synthesized by reflux method. Shown in Scheme 1, 5mM of 2-Acetyl-3-ethylpyrazine and thiosemicarbazides (L1), 5mM of 2-Acetyl-3-ethylpyrazine and 4-methylthiosemicarbazide (L2), 5mM of 2-Acetyl-3-ethylpyrazine and 4-phenylthiosemicarbazide (L3), and 5mM of 2-Acetyl-3-ethylpyrazine and 3-pyrrolethiosemicarbazide (L4) were stirred in CH3OH for 3 h at 65C. The ligands were precipitated and filtered. L1-L4 were characterized by infrared spectroscopy, electrospray ionization mass spectrometry (ESI-MS), 1H NMR, and 13C NMR (Supplementary Figs S4- S31). L1: 2-Acetyl-3-ethylpyrazine-thiosemicarbazides; yield:79.6%. Anal. Calcd (%) for C9H13N5S: C, 48.41; H, 5.87; N, 31.36; S, 16.36. Found: C, 48.32; H, 5.80; N, 31.43; S, 16.40. IR, cm-1: 3430.8 (s, amide), 3234.7 (s, NH), 3158.7 (m, aromatic hydrogen), 1598.16, 1504.69, 1459 (s, aromatic), 1396.96 (m, C=N), 1293.39 (s, thioamide), 1155, 1102.57, 880 (m, C-H), 715 (m, C=S), 596. m/z (ESI): calcd for C9H13N5S, 222.08 [M-H]-. 1H NMR (400MHz, DMSO) delta 10.48 (s, 1H), 8.55 (d, J=2.4Hz, 1H), 8.49 (d, J=2.4Hz, 1H), 8.38 (s, 1H), 7.60 (s, 1H), 3.04 (q, J=7.4Hz, 2H), 2.35 (s, 3H), 1.20 (t, J=7.4Hz, 3H); 13C NMR (100MHz, DMSO) delta 179.42, 156.21, 150.18, 148.02, 142.99, 140.68, 28.00, 15.87, 12.75.

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:
Article; Khan, Muhammad Hamid; Cai, Meiling; Li, Shanhe; Zhang, Zhenlei; Zhang, Juzheng; Wen, Xiaoan; Sun, Hongbin; Liang, Hong; Yang, Feng; European Journal of Medicinal Chemistry; vol. 182; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 951626-95-2, name is Ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate, 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 951626-95-2, Formula: C9H11N3O3

A solution of lithium hydroxide monohydrate (2.73 g, 65.0 mmol) in H20 (30.0 mL) was added to a suspension of ethyl 4-oxo-4,5 ,6,7-tetrahydropyrazolo [1,5 -a]pyrazine-2- carboxylate (2.72 g, 13.0 mmol) in THF (30 mL) and MeOH (30 mL) at 0 C. Then, the suspension was stirred at rt overnight. The solvents were removed. H20 (20 mL) wasadded. The clear solution was cooled to 0 C, conc. HC1 (5.42 mL, 65.0 mmol) was added to bring pH to 3. The suspension was stirred at 0 C for 2 h, filtered, and dried to give a white solid (2.2 g, 93%). LC-MS(ESI) m/z: 182.1 [M+H].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63744-22-9, 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

6 8-dibromo-3-iodo-imidazo[1 ,2-a]pyrazineTo a stirred solution of 8.7 g (31.4 mmol) 6,8-dibromo-imidazo[1 ,2-a]pyrazine which was prepared according to a procedure described in the Journal of Medicinal Chemistry, 1984, vol. 27, No. 2, p. 206 – 212 in 210 ml_Nu,Nu-dimethylformamide was added 7.42 g N-iodopyrrolidin-2,5-dione in one portion at 23 C. After 18 hours of stirring at 60 C, the solvent was removed in vaccuo and the residue was taken up in dichloromethane and washed with water and saturated sodium thiosulfate solution. The organic phase was dried over sodium sulphate, filtered and the solvent was evaporated to yield 9.46 g (74.8 of the title compound.

The synthetic route of 6,8-Dibromoimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; KOPPITZ, Marcus; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; SCOTT, William; WO2011/151259; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem