1458-01-1 Archives

Shutske, Gregory M. et al. published their research in Journal of Heterocyclic Chemistry in 1981 | CAS: 1458-01-1

Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1) belongs to pyrazine derivatives. Pyrazine is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, 浼?hydroxyketone, 浼?methyl ketone. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.HPLC of Formula: 1458-01-1

Synthesis of anhydro-3-mercapto-5-pyrazinyl-1,2,4-triazolium hydroxides was written by Shutske, Gregory M.. And the article was included in Journal of Heterocyclic Chemistry in 1981.HPLC of Formula: 1458-01-1 This article mentions the following:

The synthesis of some novel anhydro-3-mercapto-5-pyrazinyl-1,2,4-triazolium hydroxides (I; R = H, NH₂, NHAc; R¹ = H, NH₂; R² = Et, H, Cl; R³ = alkyl, aryl, etc.) is described. The appropriate 1-methylhydrazides II (R⁴ = Me, R⁵ = H) were condensed with R³NCS to give the thiosemicarbazides III which were cyclized to I under mildly basic conditions. A few 1,2,4-triazole-3-thiones IV were synthesized for comparison, starting with the 2-methylhdrazides (II; R⁴ = H, R⁵ = Me) and then carrying out analogous synthetic transformations. In the experiment, the researchers used many compounds, for example, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1HPLC of Formula: 1458-01-1).

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Jorner, Kjell et al. published their research in Cell Reports Physical Science in 2020 | CAS: 1458-01-1

Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1) belongs to pyrazine derivatives. Pyrazines are volatile compounds that are used in the cosmetic, food, flavor, and fragrance industries. Pyrazines undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.Related Products of 1458-01-1

Degradation of Pharmaceuticals through Sequential Photon Absorption and Photoionization in Amiloride Derivatives was written by Jorner, Kjell;Rabten, Wangchuk;Slanina, Tomas;Proos Vedin, Nathalie;Sillen, Sara;Wu Ludvigsson, Jufang;Ottosson, Henrik;Norrby, Per-Ola. And the article was included in Cell Reports Physical Science in 2020.Related Products of 1458-01-1 This article mentions the following:

Herein, the photodegradation of analogs of amiloride, which are known to undergo photosubstitution in water was reported. Model compounds built on the same scaffold undergo clean photosubstitution also in alc. solvent, where a certain amount of photodehalogenation was normally expected. Available evidence points to a mechanism starting with photoexcitation followed by photoionization to give a radical cation intermediate. Subsequent substitution reaction with the protic solvent was assisted by a general base, possibly strengthened by the proximal solvated electron. Recombination with the solvated electron generates the observed product. Quantum chem. computations revealed that excited state antiaromaticity is relieved when an electron is ejected from the photoexcited mol. by the second photon. The mechanism indicated here could have wide applicability to photoinduced degradation of similar heteroaromatic compounds in the environment, as well as to a class of increasingly popular synthetic photoredox methods. In the experiment, the researchers used many compounds, for example, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1Related Products of 1458-01-1).

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Smith, Robert L. et al. published their research in Journal of the American Chemical Society in 1979 | CAS: 1458-01-1

Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1) belongs to pyrazine derivatives. Pyrazine derivatives have antitumor, antibiotic, anticonvulsant, antituberculous and diuretic effects as well as kinase, enzymatic and potent tubulin and FtsZ polymerization inhibitory activities. Pyrazine and a variety of alkylpyrazines are flavor and aroma compounds found in baked and roasted goods. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human Granulocytes.COA of Formula: C6H7ClN4O2

Proton, carbon-13, and nitrogen-15 nuclear magnetic resonance and CNDO/2 studies on the tautomerism and conformation of amiloride, a novel acylguanidine was written by Smith, Robert L.;Cochran, David W.;Gund, Peter;Cragoe, Edward J. Jr.. And the article was included in Journal of the American Chemical Society in 1979.COA of Formula: C6H7ClN4O2 This article mentions the following:

The favored ground-state structures were determined for the novel acylguanidine diuretic, amiloride (I), and its free base using natural-abundance ¹H, ¹³C, and ¹⁵N NMR techniques and CNDO/2 theor. calculations I existed primarily in the acylamino tautomer form as planar conformer F1, whereas the free base preferred the acylimino tautomer form as planar conformer A1 (and/or A4). The dynamic mechanism(s) for the exptl. observed rapid equilibrium of the terminal amino groups in I and the free base and, when N-substituted, their substituents were explored by the CNDO/2 method. Of the six possible pathways considered for effecting N-10-N-11 interconversion in the free base a novel mechanism involving a synchronous rotation around ϕ₂ and ϕ₃ was calculated to have the lowest barrier to interconversion. Exptl. verification of this novel mechanism was attempted, but not found, by preparation of an appropriate model, II and subsequent determination of the ΔG^ values (14.7-14.8 kcal/mol) for II and pyrazine analogs using the dynamic ¹³C NMR technique in Me₂SO-d₆-CD₃OI). The free base is likely to undergo N-10-N-11 interconversion via simple ϕ₃ rotation and/or ϕ₂ rotation plus inversion. Accordingly, I must equilibrate by a ϕ₃ rotation mechanism. In the experiment, the researchers used many compounds, for example, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1COA of Formula: C6H7ClN4O2).

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

S News Discovery of 1458-01-1

The synthetic route of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-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. name: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

4-(4-Aminophenyl)ethylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride (83) A mixture of 1-H-pyrazolecarboxamidine hydrochloride (2.8 g, 19 mmol), 4-aminoethylaniline (1.3 mL, 9 mmol) and diisopropylethylamine (1.3 ml) were stirred in dry DMF (5 mL) under argon for 18 h. After this time, ether (30 ml) was added to produce a clear oil. The obtained oil (82) was washed with ether and dried under vacuum (40 mTorr) overnight. After drying 70 mg of oil was taken into dry methanol (3 mL) and 25percent NaOH (0.14 mL) was added. The reaction volume was decreased to 1.0 mL and 3,5-diamino-6-chloropyrazine-2 carboxylic acid methyl ester (0.1 g, 0.5 mmol) was added. The mixture was stirred at room temperature overnight. Another portion of 82 (0.1 g) was dissolved in methanol (1 mL), treated with 25percent NaOH (0.15 mL) and the resulting solution was added to the reaction mixture. The reaction mixture was stirred 3 h at reflux, then cooled to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in a minimal volume of DMF and separated by preparative HPLC. The obtained fractions were analyzed by LC/MS. The fractions containing product with M+H=349 were collected and the solvent was removed under reduced pressure. The residue was dissolved in 10percent HCl and evaporated to dryness to produce 83 (23.5 mg, 11percent) as a yellow solid. 1H NMR (360 MHz, DMSO-d6) delta 2.91 (m, 2H), 3.59 (m, 2H), 7.31 (d, 2H), 7.42 (m, 4H), 9.02 (br s, 2H), 9.41 (br s., 1H), 10.56 (s, 1H). 13C NMR (90 MHz, DMSO-d6) 33.1, 42.0, 108.9, 119.6, 120.7, 129.9 (2 C), 131.0 (2 C), 153.1, 154.1, 155.8, 165.2. API MS m/z=349 [C14H17ClN8O+H]+.

The synthetic route of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PARION SCIENCES, INC.; JOHNSON, Michael Ross; (49 pag.)US2015/376146; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

September 18, 2021 News The origin of a common compound about 1458-01-1

The chemical industry reduces the impact on the environment during synthesis 1458-01-1. I believe this compound will play a more active role in future production and life.

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. 1458-01-1

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 I) and NaOH (6 mol/l in water; 240 mL; 1 .44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 mL). Water (200 mL) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60°C. Yield: 99.6 g (107percent of theory). C5H5ClN4O2. ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [M-H]-.

The chemical industry reduces the impact on the environment during synthesis 1458-01-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; BLUM, Andreas; HAMPRECHT, Dieter; KLEY, Joerg; WO2013/92674; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

September 14,2021 News Brief introduction of 1458-01-1

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.

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)

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

9/14/2021 News Extended knowledge of 1458-01-1

Adding a certain compound to certain chemical reactions, such as: 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-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 1458-01-1, name: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

Example 310; Synthesis of 3,5-diamino-6-chloropyrazine-2-carboxylic acid[0247] To a solution of methyl 3,5-diamino-6-chloropyrazine-2-carbamate (5 g, 0.025 mols ) in 2:1 THF/MeOH (90 mL) was added IM LiOH (62 mL, 0.062 mols ). After the reaction was stirred at r.t. 72 hrs, IN HCl (62 mL, 0.062 mols ) was added. The reaction was filtered and washed with water (3 x 10 mL) to give 3,5-diamino-6- chloropyrazine-2-carboxylic acid as white solid 4.3 g (93 percent yield). LCMS (m/z): 189.1 (MH+); LC Rt = 1.05 min.

Reference:
Patent; NOVARTIS VACCINES AND DIAGNOSTICS, INC.; WO2008/106692; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

September 9,2021 News New learning discoveries about 1458-01-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, and friends who are interested can also refer to it.

(b) A mixture of 2.0 g (10.0 mmol) of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate and 13.5 g (22.6 mmol) of ethylene diamine was allowed to stand for 3 days at ambient temperature. The excess amine was evaporated and the residue was crystallized from ethanol. There was obtained 1.38 g (5.9 mmol, 59percent) of 3,5-diamino-6-chloro-N-(2-aminoethyl)pyrazine-2-carboxamide: mp 173°-174° C. Analysis calculated for C7 H11 ClN6 O: C, 36.45: N, 4.81; N, 36.44; Found: C, 36.50; N, 4.71; N, 36.22

Reference:
Patent; ICI Americas Inc.; US4906633; (1990); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

8-Sep-21 News Analyzing the synthesis route of 1458-01-1

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Formula: C6H7ClN4O2

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 l) and NaOH (6 mol/l in water; 240 mL; 1.44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 mL). Water (200 mL) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60° C. C5H5ClN4O2 ESI Mass spectrum: m/z=189 [M+H]+; m/z=187 [M-H]-

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KLEY, Joerg; HECKEL, Armin; US2014/323447; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

September 6,2021 News Share a compound : 1458-01-1

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference of 1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem