Tag: M.W=200-300

Application of 622392-04-5, A common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, 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.

To a solution of 2-bromo-5-iodopyrazine (CAS 622392-04-5) (250 mg, 878 muiotaetaomicron) in 0.7 ml of pyridine, was added 2-methylpropane- 1,2-diamine (116 mg, 138 mu, 1.32 mmol, 1.5 equiv.) at room temperature. The colorless solution was stirred for 16 hours at 100C. The reaction mixture was cooled and concentrated in vacuo. The crude material was used directly in the next step.

The synthetic route of 622392-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GREEN, Luke; GUBA, Wolfgang; JAESCHKE, Georg; JOLIDON, Synese; LINDEMANN, Lothar; RICCI, Antonio; RUEHER, Daniel; STADLER, Heinz; VIEIRA, Eric; WO2011/128279; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 762240-92-6, The chemical industry reduces the impact on the environment during synthesis 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, I believe this compound will play a more active role in future production and life.

Example 4 Synthesis 7-chloroacetyl-3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine of formula (VIII, Q = chlorine) 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (54.6 g, 239 mmol) is suspended in ethyl acetate (300 ml) and added, under strong stirring, with a 30% NaOH solution (100 g) and water (50 ml). After 10 minutes the phases are separated, the aqueous phase is extracted with 3×70 ml of ethyl acetate and the organic phase is dried with Na2SO4, then filtered and the solvent is evaporated off under reduced pressure to obtain a white solid (45.4 g, 236 mmol, 99% yield).

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, 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dipharma Francis S.r.l.; EP2270009; (2011); A1;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

A mixture of methyl 3-amino-5,6-dichloropyrazine-2-carboxylate (1.00 g, 4.50 mmol), (4-methylphenyl)boronic acid (0.612 g, 4.50 mmol), sodium carbonate (0.955 g, 9.01 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.18 g, 0.22 mmol) in 1,4-dioxane (18 mL) and water (2 mL) was evacuated then refilled with nitrogen. The resulting mixture was stirred at 90 C. for 2 h. The mixture was cooled to room temperature then (4-cyanophenyl)boronic acid (0.66 g, 4.50 mmol) was added, followed by another portion of [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) complexed with dichloromethane (1:1) (0.2 g, 0.2 mmol). The vessel containing the mixture was evacuated then refilled with nitrogen and stirred at 90 C. for additional 2 h. The reaction mixture was cooled to room temperature and diluted with methylene chloride, washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified on a silica gel column eluting with 0 to 25% EtOAc/DCM to give the desired product (1.2 g, 77%). LC-MS calculated for C20H17N4O2 (M+H)+: m/z=345.1. found 345.1.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1458-18-0.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Courter, Joel R.; He, Chunhong; Li, Jingwei; Lu, Liang; Sun, Yaping; Wang, Xiaozhao; Yao, Wenqing; Zhang, Colin; Zhuo, Jincong; (87 pag.)US2016/9720; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-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 6966-01-4, Recommanded Product: Methyl 3-amino-6-bromopyrazine-2-carboxylate

(4-(5-(5-Amino-6-(5-tert-butyl- 1 ,3,4-oxadiazol-2-yl)pyrazin-2-yl)- 1 -methyl- 1H- 1 ,2,4- triazol-3 -yl)piperidin- 1 -yl)-3 -(tetrahydro-2H-pyran-2-yloxy)propan- 1 -one (Example 2.1) was prepared as follows: Hydrazine hydrate (23.59 mL, 480.75 mmol) was added dropwise to a stirred mixture of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 g, 418.04 mmol) in EtOH (2 L). The mixture was heated at 50C under nitrogen. The resulting thick suspension was stirred at 50 C for 16 hours. Further hydrazine (2.5 mL) was added in one portion and the suspension was stirred at 50 C for a further 24 hours. Ethanol (500 mL) was charged to the thick reaction mixture and the mixture was allowed to cool to room temperature. The resulting suspension was filtered and the solid washed with ethanol (1 L) and dried in vacuo to give 3-amino-6-bromopyrazine-2-carbohydrazide (98 g, quantitative) as a cream solid: 1H NMR Spectrum: (DMSO-d6) 4.52 (2H, s), 7.59 (2H, s), 8.30 (1H, s), 9.74 (1H, s); Mass Spectrum [M+H]+ = 232.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-bromopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard Christophe; BERRY, David; DELOUVRIE, Benedicte; HARRIS, Craig Steven; LAMBERT-VAN DER BREMPT, Christine Marie Paul; OUVRY, Gilles; REID, Gary Patrick; TOMKINSON, Gary Peter; WO2014/114928; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3, 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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate C75-Chloro-3-( I ,3-dimethyl-I H-pyrazol-4-yl)-pyrazi n-2-ylam me To a solution of 3-bromo-5-chloropyrazin-2-amine (3.75 g, 18.01 mmol) in DME (90 mL) wasadded 1 ,3-dimethyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (4 g, 18.01 mmol), bis(triphenylphosphine)palladium(ll) chloride (0.632 g, 0.901 mmol) and Na2003 (aq.2.OM) (27.0 mL, 54.0 mmol). The reaction was heated to 90C overnight. The reaction was added to water (250m1) and the product was extracted into EtOAc (2 x 230m1). The organic phase was washed with brine, dried over MgSO4. The solids were removed by filtration, washed with EtOAc and the filtrate concentrated under vacuum. The crude product was purified by flash column chromatography, eluting with 0-10% gradient of (2M NH3 in MeOH)in DCM on a 80g Si-column, loading with DCM to give the product (2.5g)LCMS: Rt 0.81 mins; MS mlz 224.0 [M+H]+; Method 2minLowpHvol

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

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature 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: 5-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine 2 (Trimethylsilyl)acetylene (1.845 g, 2.655 mL, 18.78 mmol) was added dropwise to a solution of 3,5-dibromopyrazin-2-amine 1 (5 g, 19.77 mmol) in DMF (25 mL) Triethylamine (10.00 g, 13.77 mL, 98.85 mmol), copper(I) iodide (451.7 mg, 2.372 mmol) and Pd(PPh3)4 (1.142 g, 0.9885 mmol) were then added and the resulting solution stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc and water and the layers separated. The aqueous layer was extracted further with EtOAc and the combined organic layers washed with water, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography eluting with 15% EtOAc/Petroleum ether to give the product as a yellow solid (3.99 g, 75% Yield). 1H NMR (400.0 MHz, DMSO) delta 0.30 (9H, s), 8.06 (IH, s); MS (ES) 271.82.

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-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Charrier, Jean-Damien; Pinder, Joanne; Storck, Pierre-Henri; US2014/107093; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 642459-03-8, name is 6-Chloro-N-phenylpyrazin-2-amine, 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 642459-03-8, Computed Properties of C10H8ClN3

EXAMPLE 37 Preparation of [6- .-pyrazin-2-yl]-phenyl-amine To sodium hydride (50 mg, 1.25 mmol of a 60% dispersion in oil, 1.5 equiv) in DMSO (1 ml) was added a solution of 2-isopropylimidazole (138 mg, 1.25 mmol, 1.5 equiv) in DMSO (1 ml). The mixture was stirred 15 minutes and 6-chloro- (pyrazin-2-yl) -phenyl-amine (171 mg, 0.833 mmol, 1 equiv) was added as a solution in DMSO (1 ml). The mixture was heated to 80 C for 3 days then 130 C for a further 3 days. The title compound was purified by flash chromatography on silica (19 g, Si02), eluted with 10% MeOH-CH2Cl2, to afford 44 mg (19%); LCMS 2.06 min, iiilz [M+H] + 280.

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-Chloro-N-phenylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX TECHNOLOGY LIMITED; WO2004/4730; (2004); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6966-01-4, 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. 6966-01-4 name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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.

(iv) 3-Amino-6-bromopyrazine-2-carboxylic acid: To a solution of the product of step (iii) (200 g, 0.86 mol) in MeOH (500 mL) was added 5 N-NaOH (500 mL) slowly. The resulting mixture was stirred at 50 C for 3 hours. MeOH was removed under a reduced pressure and water (300 mL) added to the reaction mixture. The solution was acidified to pH 3 with 6N-HC1. The solution was extracted with EtOAc and washed with water. The combined organic extract was dried over Na2S04, filtered and evaporated to dryness to afford the subtitle compound (iv) as a brown yellow solid (180 g). 1H-NMR (400 MHz, CDC13) delta 8.30 (s, 1H);HPLC Retention Time = 0.850min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-bromopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FENG, Tao; SANGANEE, Hitesh, Jayantilal; WADA, Hiroki; WO2011/89416; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1082843-70-6, name is 3,5-Dibromo-2-chloropyrazine, 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 1082843-70-6, Product Details of 1082843-70-6

[0955] Into a 250 mL sealed tube was placed compound90d (50.0 g, 184 mmol) andNH40H (150mL). The resultingmixture was stirred overnight at 100 C. Uponcooling, a solidwas collected by filtration and dried in an oven under reducedpressure to obtain the compound 90e as a grey solid (28.0 g,66% yield), which was used in next step without furtherpurification.

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; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 5900-13-0, The chemical industry reduces the impact on the environment during synthesis 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, I believe this compound will play a more active role in future production and life.

General procedure: Azaheteroaryl halide (1 mmol), catalyst (0.005-0.05 mol %) and 1M aq. Na2CO3 (1.1 mL) were stirred in a mixture of H2O-EtOH(1:2, 5 mL). The arylboronic acid (1.1 mmol) was added to the above mixture and stirring was continued for required time at 60 C. After the requisite time, reaction mixture was diluted with ethyl acetate and the catalyst was separated by centrifugation. The centrifugate was dried over anhydrous sodium sulphate and evaporated. Then the product was analyzed by GC-MS or LC-MS.The solution was concentrated and chromatographed on a silicagel column with n-hexane-ethyl acetate (4:1) as the eluting solvent to give the coupled product. The product was confirmed by 1H and 13C NMR spectral analysis. The used catalyst was washed with water, ethanol and dichloromethane, and dried under vacuum before reuse.

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, 5-Bromo-3-methoxypyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ganesamoorthy; Muthu Tamizh; Shanmugasundaram; Karvembu; Journal of Organometallic Chemistry; vol. 862; (2018); p. 76 – 85;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem