Tag: M.W=200-300

Synthetic Route of 63744-22-9, A common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

Intermediate Example 10-1 : Preparation of 6,8-dibromo-3-iodo-imidazo[1 ,2- aj yrazineTo a stirred solution of intermediate example 1 -1 (8.7 g g, 31 .4 mmol) in DMF (210 mL) was added NIS (7.42 g, 33 mmol, 1 .05 eq) in one portion at rt. After 18 h stirring at 60 C, the solvent was removed in vaccuo and the residue was taken up in DCM 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 %) 6,8-Dibromo-3-iodo-imidazo[1 ,2-a]pyrazine: 1H- NMR (300 MHz, CDC ): delta = 8.22 (1 H, s), 7.91 (1 H, s) ppm

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; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80234; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]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. Formula: C7H3Cl2N3

Intermediate 25: 1 ,1-Dimethylethyl (3 ~)-3-fr(7-chloropyridor3,4-blpyrazin-5- yl)amino1methylV4-methyl-1-piperazinecarboxylate; 1 , 1-Dimethylethyl (3S)-3-(aminocarbonyl)-4-methyl-1-piperazinecarboxylate (0.5g, 2.055mmol) was dissolved in dry tetrahydrofuran (THF) (10ml) and borane- tetrahydrofuran complex (8ml, 8.00mmol) was added. The reaction was refluxed under nitrogen overnight. A further portion of borane-tetrahydrofuran complex (8ml, 8.00mmol) was added and the reaction was refluxed under nitrogen for a further 24h. After cooling, the reaction was cooled further in an ice bath and quenched by the addition of methanol (25ml) and 1 M HCI (5ml), stirred for 90min and left standing at room temperature for 2h. Ethyl acetate (25ml) was added and the layers were separated. The aqueous was extracted with ethyl acetate. The combined organics were dried using a hydrophobic frit and evaporated in vacuo to give a white solid (270mg). TLC (10% MeOH/DCM, KMn04) looked like starting material. The aqueous layer was neutralised with 2M NaOH and extracted with DCM (x3). The combined organics were washed with brine, dried using a hydrophobic frit and evaporated in vacuo to give 1 , 1-dimethylethyl (3f~)-3-(aminomethyl)-4-methyl-1- piperazinecarboxylate as a crude colourless oil (313mg). 1 , 1-dimethylethyl (3R)-3- (aminomethyl)-4-methyl-1-piperazinecarboxylate (143mg, 0.624mmol) and diisopropylethylamine (0.131 ml, 0.750mmol) were added to a solution of 5,7- dichloropyrido[3,4-b]pyrazine (100mg, 0.500mmol) in dry N-methyl-2-pyrrolidone (NMP) (2ml). The reaction was heated at 130C in the microwave for 30min. After cooling, the reaction was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (x2). The combined organics were washed with brine, dried using a hydrophobic frit and evaporated to give an orange oil. The residue was loaded in dichloromethane and purified on silica (25g) using a 0-100% ethyl acetate/cyclohexane gradient. Appropriate fractions were combined and evaporated to give the title compound as yellow oil (162mg).LCMS (Method A): Rt = 1.2min, MH+ = 393/395

The synthetic route of 5,7-Dichloropyrido[3,4-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1458-16-8,Some common heterocyclic compound, 1458-16-8, name is Methyl 3-amino-6-iodopyrazine-2-carboxylate, molecular formula is C6H6IN3O2, 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 dimethylformamide (60 ml) suspension of copper (II) bromide (19.2 g, 86.0 mmol) raised in temperature to 50C, t-butyl nitrite (5.7 ml, 43.0 mmol) was added and subsequently a dimethylformamide (60 ml) suspension of 3-amino-6-iodopyrazine-2-carboxylic acid methyl ester (see Patent Document: WO2006/015124)(12.0 g, 43.0 mmol) was added dropwise and the mixture was stirred for one hour. The reaction mixture was charged with t-butyl nitrite (11.4 ml, 86.0 mmol) and was further stirred for 30 minutes at an external temperature of 50C. The reaction solution was poured into a 3 M aqueous hydrochloride solution (60 ml) of sulfamic acid (7.6 g) under ice cooling and extracted with ethyl acetate, dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: hexane: ethyl acetate = 5:1 to 1:1]. The resultant low polarity product was washed with hexane-ethyl acetate to obtain 3-bromo-6-iodopyrazine-2-carboxylic acid methyl ester (6.38 g) in the form of a white solid substance. A high-polarity product was washed with ethyl acetate to obtain 3-hydoxy-6-iodopyrazine-2-carboxylic acid methyl ester (2.70 g) in the form of a yellow solid substance. 3-Bromo-6-iodopyrazine-2-carboxylic acid methyl ester MS (ESI): 342 (M+1) 1H NMR (300 MHz, CDC13) delta ppm 4.02 (d, J = 0.55 Hz, 3 H) 8.72 (s, 1 H) 3-Hydoxy-6-iodopyrazirie-2-carboxylic acid methyl ester MS (ESI): (ES+) 281 (ES-) 279 1H NMR (300 MHz, DMSO) delta ppm 3.82 (s, 2.53 H) 3.84 (s, 0.47 H) 8.35 (s, 0.78 H) 8.39 (s, 0.22 H) 12.69 – 13.03 (br, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-6-iodopyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2157090; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 24241-18-7, 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Synthesis of Compound (A’) as Described in the General Reaction Scheme; 2-chloro-3,5-dibromo-pyrazineTo a well stirred solution of 2-amino-3,5-dibromopyrazine (3.21 g, 12.692 mmol) in DCM (20 1 mL) cooled to 0 C. is added TiCl4 (2.41 g, 12.692 mmol, 1.00 equiv.) in one portion, thus giving a dark red slurry. t-Butylnitrite (2.62 g, 25.385 mmol, 2.00 equiv.) is then added dropwise, causing the solution to turn bright yellow. The ice bath is then removed and the reaction is then allowed to proceed at room temperature. More TiCl4 (1.50 g, 1.2 equiv.) is added and the mixture is stirred further for one hour. At that point an orange solution has formed and LC-MS shows full conversion of the starting material to the desired product which ionises very poorly. Water (100 1 mL) is added to the reaction, forming an emulsion. DCM (50 1 mL) is added, and the DCM layer is separated, and the aqueous layer is further extracted with DCM (3¡Á50 mL) until the DCM layer is colorless. The DCM layers are gathered, washed with brine and dried over anhydrous Na2SO4, to yield after solvent removal, compound A’ (2.81 g, 82%) as an orange oil, which is used as such in the following step.

The synthetic route of 2-Amino-3,5-dibromopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andrews, Martin James Inglis; Chambers, Mark Stuart; Van De Poel, Herve; Bar, Gregory Louis Joseph; US2009/286798; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, 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 63744-22-9, HPLC of Formula: C6H3Br2N3

Step-(iii): Synthesis of (4-((6-bromoimidazo [1, 2-a] pyrazin-8-yl) amino) phenyl)(morpholino) methanone:To a stirred solution of Intermediate-lOb (7.0 g, 19.6 mmol), Intermediate-8b (4.0 g, 19.6 mmol) in 70 mL of DMF was added, DIPEA (10.68 mL, 58.82 mmol) and stirred at 110C for 20h. The reaction mixture was distilled under a reduced pressure to remove the solvent. Theresidue was taken in water and extracted with DCM (2 x 250 mL). The combined organic phases were washed with brine, dried over sodium sulphate and concentrated. The obtained crude product was purified by colunm chromatography using 100-200 mesh silica gel and 5% MeOH in DCM as eluent to give the titled product as a pale brown viscous solid (4.8 g, 61%); 1H NMR (400 MHz, DMSO-d6): oe 10.21 (s, 1H), 8.33 (s, 1H), 8.07 (d, 2H, J=8 Hz), 7.98 (s, 1H), 7.97 (s,1H), 7.43 (d, 2H, J=8.8 Hz), 3.61-3.5 1 (m, 8H); MS (ES) m/z 402 (M+1).

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; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125410; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 110223-15-9, name is 2-Amino-3-benzyloxypyrazine, 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 110223-15-9, Safety of 2-Amino-3-benzyloxypyrazine

General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

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, 2-Amino-3-benzyloxypyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Elkamhawy, Ahmed; Park, Jung-eun; Hassan, Ahmed H.E.; Pae, Ae Nim; Lee, Jiyoun; Paik, Sora; Park, Beoung-Geon; Roh, Eun Joo; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 268 – 278;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 173253-42-4, These common heterocyclic compound, 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine, 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.

7. 2,6-Diamino-3-bromopyrazine A suspension of 2-chloro-3-bromo-6-aminopyrazine (15 g, 0.072 mole) in absolute ethanol (150 ml) and 0.880 ammonia (375 ml) was stirred and heated in an autoclave at 160 C. and 20 atm. for 16 hrs. The cooled mixture was evaporated in vacuo and extracted with hot methanol (3*100 ml). The combined methanol extracts were evaporated in vacuo. The residue was dissolved in hot chloroform, dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was triturated with 40-60 C. petroleum ether, filtered, and dried in vacuo. Yield 5.51 g (40%), M.p. 176-178 C.

Statistics shows that 2-Amino-5-bromo-6-chloropyrazine is playing an increasingly important role. we look forward to future research findings about 173253-42-4.

Reference:
Patent; Glaxo Wellcome, Inc.; US6255307; (2001); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1215852-11-1, A common heterocyclic compound, 1215852-11-1, name is 7-tert-Butyl 3-ethyl 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-3,7(8H)-dicarboxylate, molecular formula is C13H20N4O4, 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.

Step A: tert-Butyl 3-(2-hydroxypropan-2-yl)-5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate. To a solution of 7-tert-butyl 3-ethyl 5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazine-3,7(8H)-dicarboxylate (0.9 g, 3.04 mmol) in THF (20 mL) at 0C, was added 3 M methylmagnesium iodide in diethyl ether (3.04 mL, 9.11 mmol) dropwise. The reaction was stirred overnight at RT. After 16 hours, the reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic layer was concentrated to provide tert-butyl 3-(2-hydroxypropan-2- yl)-5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate as a white powder (0.4 g, 46.6 % yield).

The synthetic route of 1215852-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; BODE, Christiane, M.; CHENG, Alan, C.; CHOQUETTE, Deborah; LEWIS, Richard, T.; POTASHMAN, Michele, H.; ROMERO, Karina; STELLWAGEN, John, C.; WHITTINGTON, Douglas, A.; WO2012/18668; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 63744-22-9, The chemical industry reduces the impact on the environment during synthesis 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

General procedure: 6,8-dibromoimidazo[1,2-a]pyrazine (6, 1.86 g, 6.72 mmol) was added to asolution of 3a-3c, 5a-5e (5.6 mmol), DIPEA (1.4 mL, 8.4 mmol) inisopropanol (60 mL), stirred at 85 C for 8 h, and then the solvent wasevaporated to dryness. The crude product was purified by columnchromatography to obtain the desired intermediates 7a, 11a-11 g.

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, 6,8-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fan, Yan; Huang, Zhi; Li, Yao; Qin, Zhongxiang; Wang, Cheng; Wang, Tianqi; Wang, Xin; Xiang, Rong; Yang, Shengyong; Bioorganic Chemistry; vol. 95; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5900-13-0,Some common heterocyclic compound, 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, molecular formula is C5H6BrN3O, 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 46 Sodium hydride (60% dispersion in oil; 0.094 g) was added to a solution of 2-amino-5-bromo-3-methoxypyrazine (0.159 g) in dimethoxyethane (4 ml). The solution was stirred for 10 minutes and then 4-nitrophenyl 4′-isobutyl-2-biphenylsulphonate (0.321 g) was added. The solution was allowed to stand for 5 hours and then water (20 ml) was added. 2M Hydrochloric acid (2 ml) was added and the mixture was extracted with ethyl acetate (2*30 ml). The extracts were dried (MgSO4) and volatile material was removed by evaporation. The residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column. The resulting solid was recrystallized from a mixture of ether and hexane to give N-(5-bromo-3-methoxy-2-pyrazinyl)-4′-isobutyl-2-biphenylsulphonamide (0.09 g), m.p. 154-156 C.; 1 H NMR (d6 -DMSO): 0.9 (d,6H), 1.8-2.0 (m,1H), 2.5 (d,2H), 3.85 (s,3H), 7.1 (s,4H), 7.3 (d,1H), 7.5-7.7 (m,2H), 7.8 (br s,1H), 8.05 (d,1H), 10.2-10.3 (br, 1H); mass spectrum (+ve FAB, methanol/NBA): 478 (M+H)+.

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

Reference:
Patent; Zeneca Limited; US5861401; (1999); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem