Tag: M.W=200-300

Electric Literature 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

Synthetic Route of 369638-68-6, 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. 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

tert-butyl 5-methylpyrazin-2-yl carbamate (6.27 g, 30.0 mmol) was weighed and dissolved in 30 mL dichloromethane, and in an ice water bath, 20 mL trifluoroacetic acid was added slowly. It was moved to react at room temperature for 1 hour, rotate evaporated to dryness to remove the solvent, and was used for the next step directly.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (5-methylpyrazin-2-yl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KBP Biosciences Co., Ltd.; ZHANG, Yan; ZHANG, Min; LO, HoYin; (52 pag.)EP2781508; (2014); 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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 117719-17-2

A mixture of intermediate 1-02 (360 mg, 1.35 mmol), indazole-4-boronic acid hydrochloride (600 mg, 2.97mmol), K2C03 (2 mE of saturated solution), PdC12(dppf). DCM (112 mg, 0.135 mmol) in DME (5 mE) was heatedunder microwave irradiation for 10 mm at 130 C. Thereaction mixture was filtered through a celite pad, washingwith DCM. The filtrate was dried over Na2SO4 and concentrated. The crude was purified by flash column chromatography (Isolute Si 1110 g cartridge) eluting with a gradient ofDCMJMeOH (from 100% to 90:10) to yield 250 mg of theintermediate 1-03 pure (Y: 62%).

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 117719-17-2.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); Serrano Marugan, Manuel; Pastor Fernandez, Joaquin; Martinez Gonzalez, Sonia; Ortega Molina, Ana; Bischoff, James R.; Oyarzabal Santamarina, Julen; (220 pag.)US9993554; (2018); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 87486-34-8,Some common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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 109c 5-Bromo-3-(l-cyclopropyl-lH-pyrazol-4-ylamino)-l-methylpyrazin- -one 109cCGIPHARM60WOA 100-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet was charged with 109b (378 mg, 3.07 mmol), 3,5- dibromo-l-methylpyrazin-2(lH)-one (906 mg, 3.38 mmol), cesium carbonate (3.00 g, 9.21 mmol), and 1,4-dioxane (45 mL). After bubbling nitrogen through the resulting suspension for 30 min, Xantphos (151 mg, 0.261 mmol) and tris(dibenzylidene-acetone)dipalladium(0) (141 mg, 0.154 mmol) were added, and the reaction mixture was heated at reflux for 3 h. After this time, the mixture was cooled to room tempera-ture and diluted with ethyl acetate (150 mL) and water (30 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 45 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 0percent to 10percent methanol/methylene chloride) to afford a 28percent yield (266 mg) of 109c as an off-white solid: mp 228-230 °C; ]H NMR (300 MHz, DMSO-i3/4) delta 9.90 (s, 1H), 8.06 (s, 1H), 7.69 (s, 1H), 7.21 (s, 1H), 3.70 (m, 1H), 3.41 (s, 3H), 0.96 (m, 4H); MS (ESI+) m/z 310.0 (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 3,5-Dibromo-1-methylpyrazin-2(1H)-one, its application will become more common.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; CURRIE, Kevin S.; WANG, Xiaojing; YOUNG, Wendy B.; WO2012/31004; (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. 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H3BrClN3

To a solution of 1-69 (100 mg, 0.2 mmol) in DMF are added 2-amino-5-bromo-6- chloropyrazine (51 mg, 0.24 mmol), Tetrakis (triphenylphosphine)palladium (0) (24 mg, 0.02 mmol) and 2M Na2C03 solution (2M aqueous)(0.5 mL, 1 mmol). The mixture is heated to 100 C for 1 hour in a microwave reactor. The mixture is cooled down and is extracted with H20 and EtOAc. The combined organic layer is dried with MgS04 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2C12 as the eluent to afford 1- 155 (86 mg) (m/z: 493.2 [M++H]).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John; LO, Ho Yin; LOKE, Pui Leng; LIU, Weimin; MORWICK, Tina Marie; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee; WO2012/24150; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 642459-03-8,Some common heterocyclic compound, 642459-03-8, name is 6-Chloro-N-phenylpyrazin-2-amine, molecular formula is C10H8ClN3, 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 36 36A. Preparation of Phenyl- [6- (2. 2, 2-triiluoroethoxy-pyrazm-2-yl]-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, 2, 2-trifluoroethanol (90 1ll, 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 80C for 3 days. The title compound was purified by flash chromatography on silica (19 g, Si02), eluted with 25% ethyl acetate-petrol, to afford 110 mg (49%) ; LCMS 3.95 min, [M+H]”270.; 36B. Preparation of (6-Methylsulfanyl-pyrazin-2-yl)-phenyl-amine The title compound was obtained as a side product of the method of 36A and was isolated as a minor fraction of the reaction products following flash chromatography on silica (19 g, Si02), eluting with 25% ethyl acetate-petrol, to afford 3 mg (1%); LCMS 2.76 min, m/z [M+H] + 218.

The synthetic route of 642459-03-8 has been constantly updated, and we look forward to future research findings.

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

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, Recommanded Product: 1458-01-1

(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

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.

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

Synthetic Route of 24241-18-7, These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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 stirred suspension of 2-amino-3,5-dibrompyrazine (427 g, 1688mmol) in water (6.4 L) / THF (482 mL), at rt was added bromacetaldehyde-diethylacetal (998 g, 5065 mmol) in one portion. After stirring under reflux for 4 h, the clear orange solution was stirred for an additional 15 h at rt. The suspension was filtered, and the remaining solid was washed with MeOH (2 L) and dried in vaccuo at 60 C to yield 6,8-dibromo-imidazo[1 ,2-a]pyrazine as an off-white solid (500 g, 107% with residual MeOH): 1H-NMR (300 MHz, d6-DMSO): delta =9.02 (s, 1 H), 8.23 (d, 1 H), 7.89 (d, 1 H) ppm. UPLC-MS: RT = 0.80 min; m/z 277.9 [MH+]; required MW = 276.9.

Statistics shows that 2-Amino-3,5-dibromopyrazine is playing an increasingly important role. we look forward to future research findings about 24241-18-7.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SIEMEISTER, Gerhard; BADER, Benjamin; WENGNER, Antje, Margret; MUMBERG, Dominik; KOPPITZ, Marcus; KLAR, Ulrich; KROEMER, Guido; VITALE, Ilio; JEMAA, Mohamed; WO2014/20041; (2014); 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C5H2BrF3N2

example 3o (100 mg, 0.55 mmol), 2-Chloropyrimidine (76.3 mg, 0.67 mmol) and N,N- diisopropylethylamine (192 mu, 1.11 mmol) are dissolved in 1 ml of DMSO and the reaction mixture is heated in a microwave reactor 30 minutes at 120C. The crude product is partitioned between Et20 and water; the organic layer is then separated and concentrated under reduced pressure to obtain the title compound (158 mg). UPLC-MS (Method 2): Rt = 0.76 MS (ES+): m/z = 259 [M+H]+ . Example 37a is synthesized as described for example 28a using example 3r (70 mg, 0.35 mmol) instead of example 3o, 2-Bromo-5-(Trifluoromethyl)pyrazine (102 mg, 0.45 mmol) instead of 2-Chloropyrimidine, N,N-diisopropylethylamine (239 mu, 1.38 mmol) and 1 ml of DMSO. The mixture is heated in a microwave reactor during 30 minutes at 120C. The crude product is partitioned between Et20 and water then the organic layer is separated and concentrated under reduced pressure; the residue is purified by preparative HPLC-MS to obtain the title compound (70 mg, 44 % yield) as trifluoroacetate salt. UPLC-MS (Method 1): Rt = 0.90 MS (ES+): m/z = 349 [M+H]+

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0,Some common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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.

Methyl 3-amino 5,6-dichloro-2-pyrazinecarboxylate (10 g, 45 mmol) was placed in a three-necked round bottom flask flushed with nitrogen, equipped with a bubbler and a gas condensor. The round bottomedflask and condensor were cooled to -80 C using a dry ice in acetone bath. Gaseous ammonia (500 mL) was condensed into the flask over a period of 1.5 h. Thereaction mixture was allowed to warm to reflux and maintained at reflux for a period of10 h. The ammonia then was allowed to evaporate from the flask (fume hood!) and the solid obtained was dried under high vacuum overnight to provide 3-amino-5,6-dichloro-2-pyrazinecarboxamide 4 (9.5 g, 100%) as solid,

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-5,6-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Article; Massey, Archna P.; Harley, William R.; Pasupuleti, Nagarekha; Gorin, Fredric A.; Nantz, Michael H.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2635 – 2639;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem