Month: September 2021

Application of 5049-61-6, These common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, 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 1: Synthesis of 5-bromopyrazin-2-amine To a stirred solution of pyrazin-2-amine (3 g, 31.545 mmol) in anhydrous DCM (30 mL) was added NBS (5.6 g, 31.54 mmol) under nitrogen and stirred at 0 C. for 1 h. Progress of reaction was monitored by TLC. After reaction completion DCM was added and washed with water. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Crude was purified by silica gel (100-200 mesh) column chromatography using 70% DCM/hexane to 10% ethyl acetate in hexane as eluent to yield 5-bromopyrazin-2-amine (3.4 g, 62.9%) as white solid. MS: 175.1 [M++1]

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mankind Pharma Ltd.; Patil, Rakesh Ishwar; Verma, Jeevan; Shah, Dharmesh; Ali, Sazid; Bapuram, Srinivasa Reddy; Rai, Santosh Kumar; Kumar, Anil; (146 pag.)US2017/291910; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 77112-52-8, These common heterocyclic compound, 77112-52-8, name is Ethyl imidazo[1,2-a]pyrazine-2-carboxylate, 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.

10% Pd/C (40 mg) was added to a solution of ethyl imidazo[1,2-a]pyrazine-2-carboxylate (410 mg, 2.15 mmol) and conc.HCl (0.5 mL) in EtOH (9.5 mL) and stirring was continued under a hydrogen atmosphere for 16 h. The reaction mixture was filtered over a celite bed and the filtrate was concentrated under reduced pressure to afford the crude product, which was purified by washing with diethyl ether and dried to afford 400 mg of the title compound as a yellow hygroscopic solid. MS (ESI): m/z 196 (M+H).

The synthetic route of 77112-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; Sasmal, Pradip Kumar; Ahmed, Shahadat; Prabhu, Ganesh; Tehim, Ashok; Paradkar, Vidyadhar; Dattatreya, Marahanakuli Prasanna; Mavinahalli, Nanjegowda Jagadeesh; US2015/5280; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 40155-47-3, name is 3-Methoxypyrazine-2-carboxylic acid, 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. Product Details of 40155-47-3

[0423] A solution of 3-amino-4-(4-(2,4-difluorophenoxy)piperidin-l-yl)benzonitrile (50 mg, 0.152 mmol), 3~niethoxypyrazme-2-carboxyiie acid (46.8 mg, 0.304 mmol), HATU (115 mg, 0.304 mmol) and DIPEA (106 mu,, 0.607 mmol) in DMF (759 muEpsilon) was stirred on a hot plate at 80C overnight. The reaction mixture was filtered through a Millipore filter, diluted with DMF and MeOH, and purified by HPLC (Shimadzu) eluting with a gradient of ACN in water (basic mode) to give the title compound as a light brown solid (68.7 mg, 97%). .H NMR (400 MHz, CDCb) delta ppm 2.07 – 2.18 (m, 2 H), 2.19 – 2.28 (m, 2 H), 2.91 (ddd, J=l 1.68, 8.02, 3.28 Hz, 2 H), 3.26 (ddd,./ 1 1.62. 7.58, 3.54 Hz, 2 H), 4.18 (s, 3 H), 4.37 – 4.45 (m, 1H), 6.78 ·· 6.86 (m, 1H), 6.90 (ddd,.7=11, 12, 8.34, 3.03 Hz, 1H), 7.03 (td,.7=9.09, 5,56 Hz, 1H), 7.23 (d,.7=8,34 Hz, 1H), 7.41 (dd, J=8.34, 2.02 Hz, 1H), 8.26 (d, J=2.27 Hz, 1H), 8.41 (d, J=2.53 Hz, 1H), 8.93 (d,./ 1.77 Hz, 1H), 10.62 (s, 1H); ESI-MS m/z [M+H}+ 466.2.

The synthetic route of 3-Methoxypyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); 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. 5049-61-6, name is Pyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., name: Pyrazin-2-amine

A solution of aminopyrazine (1 g, 10.5 mmol) and chloroacetaldehyde (50% wt in H2O; 1.98 g, 12.6 mmol) in 1.6 mL of EtOH was heated at 900C in a sealed tube for 5 h. Upon cooling to ambient temperature, the reaction mixture was concentrated and diluted with dichloromethane (DCM). The organic layer washed with saturated aqueous NaHCO3 then dried over MgSO4 and concentrated. The crude product was purified by silica gel flash chromatography (eluted with 10% MeOH/DCM) to provide 0.8 g of product.

According to the analysis of related databases, 5049-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; WO2007/75869; (2007); A2;,
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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 55557-52-3

An aqueous K2CO3 solution (2.0 M, 30 mL) is added to a solution of 3-chloro- pyrazine-2-carbonitrile (21.5 mmol) and the respective phenylboronic acid (21.5 mmol) in DME (65 mL). Triphenylphosphine (3.21 mmol) and palladium(II) acetate (1.06 mmol) are added and the mixture is stirred at 900C for 16 h and allowed to reach RT. EtOAc is added and the mixture is filtered through Celite, dried over MgSO4 and concentrated in vacuo to give the respective carbonitrile derivative which is diluted with MeOH (100 mL) and aqueous NaOH solution (4.0 M, 160 rnL). The mixture is stirred at 85C for 16 h, cooled to RT and concentrated partially in vacuo to remove methanol. Water and cone, hydrochloric acid are added (pH ~ 2) and the obtained precipitate is filtered off. The residue is dissolved in a mixture of EtOAc and DCM, dried over MgSO4 and concentrated in vacuo to give the desired acid derivative.3-(3-Methoxy-phenyl)-pyrazine-2-carboxylic acid prepared by reaction of S-chloro-pyrazine-l-carbonitrile with 3-methoxybenzene- boronic acid. LC-MS (A): tR = 0.71 min; [M+H]+ = 231.5.

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; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; BROTSCHI, Christine; KOBERSTEIN, Ralf; SIEGRIST, Romain; SIFFERLEN, Thierry; TRACHSEL, Daniel; WILLIAMS, Jodi T.; WO2010/44054; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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.

0.15 eq. palladium (II) acetate and 0.2 eq. 1,1′-bis(diphenylphosphino)-ferrocene were combined in dimethylformamide under nitrogen and heated to 50 C. for 20 minutes. R3 and n are each as defined herein. The reaction was allowed to cool to room temperature and 1.0 eq. of the pyrazine, 1.5 eq. of the boronic acid and 1.15 eq. of triethylamine were added. The reaction was heated to 90 for 12 hours and allowed to cool to room temperature. The DMF was removed by rotary evaporation. The crude reaction mixture was dissolved in chloroform and washed twice with 1N aq. HCl and then twice with saturated aq. NaHCO3 solution. The organic layer was dried over sodium sulfate, filtered and concentrated. Material was purified by silica gel chromatography using 100% chloroform as eluent.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2004/180905; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-29-5, 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. 33332-29-5 name is 2-Amino-5-chloropyrazine, 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.

General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, 5-chloropyrazin-2-amine (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

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

Reference:
Article; Zitko, Jan; Mindlova, Al?b?ta; Vala?ek, Ond?ej; Jand’ourek, Ond?ej; Paterova, Pavla; Janou?ek, Ji?i; Kone?na, Klara; Dole?al, Martin; Molecules; vol. 23; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1458-01-1, The chemical industry reduces the impact on the environment during synthesis 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

EXAMPLE 4 A mixture of 1-beta-aminoethylamino-3-alpha-naphthoxypropan-2-ol (3.9 g.) and methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (1.1 g.) was heated at 90° C. for 25 hours, cooled and chromatographed on a silica column (Merck `60`, 50 g., column 140 mm.long and 32 mm.diameter) using a 9:1 v/v mixture of chloroform and methanol as eluant. The fractions containing a product with an Rf of 0.2 when examined by thin layer chromatography using the above solvent system were collected, combined and evaporated to dryness under reduced pressure. The residue was converted into a hydrogen oxalate salt by a similar procedure to that described in Example 1, and the salt was crystallized from ethanol. There was thus obtained 3,5-diamino-6-chloro-N-beta-(2-hydroxy-3-alpha-naphthoxypropylamino)ethylpyrazine-2-carboxamide hydrogen oxalate, m.p. 224°-226° C. (with decomposition)

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 3,5-diamino-6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imperial Chemical Industries plc; US4550111; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5521-58-4, 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 5521-58-4 as follows.

(a) A solution of bromine (0.11 ml) in chloroform (20 ml) was added dropwise over 20 minutes to a solution of 2-amino-5-methylpyrazine (0.218 g) in chloroform (30 ml) which was protected from light. The reaction mixture was stirred for 90 minutes after addition was complete and was then washed with water (50 ml). The organic phase was dried (MgSO4) and volatile material was removed by evaporation to give a yellow oil. The oil was purified by elution with dichloromethane through a silica gel Mega Bond Elut column to give 2-amino-3-bromo-5-methylpyrazine (0.286 g) as a white solid, m.p. 51-52 C.; mass spectrum (+ve CI): 188 (M+H)+.

According to the analysis of related databases, 5521-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeneca Limited; US5866568; (1999); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products 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