Tag: M.W=200-300

Electric Literature of 313340-08-8,Some common heterocyclic compound, 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, molecular formula is C7H7Cl2N3O, 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.

Preparation Example 210 A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (500 mg), 5-methyl-6-(4-methylpiperazin-1-yl)pyridin-3-amine (470 mg), diisopropylethylamine (800 muL), and dioxane (10 mL) was stirred in a microwave reaction device at 150 C. for 30 minutes. After leaving to be cooled, water was added thereto, and the precipitated solid was collected by filtration and then dried under reduced pressure to obtain 5-chloro-6-ethyl-3-{[5-methyl-6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino}pyrazine-2-carboxamide (210 mg) as a yellow solid.

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-Dichloro-6-ethylpyrazine-2-carboxamide, its application will become more common.

Reference:
Patent; ASTELLAS PHARMA INC.; Matsuya, Takahiro; Kondoh, Yutaka; Shimada, Itsuro; Kikuchi, Shigetoshi; Iida, Maiko; Onda, Kenichi; Fukudome, Hiroki; Takemoto, Yukihiro; Shindou, Nobuaki; Sakagami, Hideki; Hamaguchi, Hisao; US2014/323463; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-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.

A suspension of S-amino-beta-bromo-pyrazine^-carboxylic acid (0.5g, 2.3 mmol) and 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenylboronic acid (patent WO 2003076422, 1.28g, 4.6 mmol) in MeCN (20ml) was treated with K2CO3 (3.8g, 27.5 mmol) in H2O (5ml) under nitrogen at room temperature. The mixture was stirred for 10 min before adding bis(triphenylphosphine)palladium dichloride (0.08g, catalytic) and stirred at 9O0C for 3 hr. The cooled reaction mixture was dilute with H2O (20ml), basified to ph4, filtered to remove catalyst and evaporated. The residue dissolved in DCM (200ml), washed with brine, dried (MgSO4) and condensed. The solid residue was subjected to flash column chromatography on silica eluting gradient of hexane to (2:1 , v/v) ethyl acetate and hexane to give title compound (0.38g, 44%) as a yellow solid; LC/MS: Rt 2.78 (Method A) [M+H]+ 374.

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERNALIS (R & D) LIMITED; WO2008/38010; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-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. HPLC of Formula: C6H5Cl2N3O2

Examples 54 and 55222.03 140.57[0266] Methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate, (3.2 gm, 0.0144 moles) and benzoyl chloride (7.03 gm, 0.05 moles) are combined in chloroform (50 mL) and pyridine (8 mL) is added. This mixture is stirred at 50C overnight. Additional portions of benzoyl chloride (3.5.0 gm, 0.025 moles) and pyridine (4 mL) are added and heating is continued at 65C overnight. The solution is cooled and methanol (25 mL) is added. After stirring for 30 minutes, the solvents are removed under reduced pressure. The solid residue is recrystallized from n-butanol.

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

Reference:
Patent; JANUS BIOTHERAPEUTICS, INC.; LIPFORD, Grayson, B.; ZEPP, Charles, M.; WO2012/167046; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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 87486-34-8, Product Details of 87486-34-8

Example 186a 5-Bromo-1-methyl-3-(pyridin-3-ylamino)pyrazin-2(1H)-one 186a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with pyridin-3-amine (940 mg, 10 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (5.4 g, 20 mmol), i-propanol (50 mL), and di-i-propylethylamine (10 mL). The mixture was heated at reflux for 5 h. After the completion of the reaction, it was cooled to room temperature. The solvent was removed under reduced pressure. The crude was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 186a (1.4 g, 50percent) as a yellow solid. MS-ESI: [M+H]+ 281.6.

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; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1196152-38-1, 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

1 ,1 -dimethylethyl (1 S,4S,6S)-4-(aminomethyl)-3-azabicyclo[4.1.0]heptane-3- carboxylate D29 (400 mg) and 2-bromo-5-(trifluoromethyl)pyrazine (401 mg, 1.767 mmol) were dissolved in DMF (2 ml) then sodium carbonate (375 mg, 3.53 mmol) was added and the mixture was heated to 50 0C for 2 hours. DMF was concentrated under vacuum and the residue was taken up with DCM (3 ml) and washed with NaHCO3 saturated solution (4 ml). The organic phase was filtered through a phase separator tube, concentrated under vacuum and purified by silica gel chromatography (Biotage SP- column size 25 g SNAP using Cy:EtOAc = 8:2 to 2:8 as eluent). It was recovered the title compound D30 (300 mg)

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

Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; CASTIGLIONI, Emiliano; DI FABIO, Romano; PAVONE, Francesca; WO2010/63662; (2010); 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Amino-6-bromopyrazine-2-carboxylic acid

-Amino-6-bromopyrazine-2-carboxylic acid (53.59 g, 0.229 mol) and 4-hydroxy-3-aminopyridine (33.64 g, 0.275 mol) were mixed in THF (500 mL) and triethyl amine (115.86 g, 1.145 mol) was added. The mixture was stirred at 25 for 10 min. The temperature was raised to 55 C. and T3P (218.90 g, 0.344 mol) was added. The mixture was stirred at 55 C. for 30 min. Water (150 mL) was added at 55 C. and the mixture was stirred for 2 h at 55 C. Solvents were distilled of until fractions at 55-80 C. was removed.Acetonitrile (500 mL) was added followed by water (350 mL) while maintaining the temperature at 75 C. The mixture was stirred for 2 h at 75 C. The solid was isolated by filtration. The solid was washed with water (250 mL) followed by acetonitrile (250 mL). The solid was dried under vacuum at 80 C. for 5 h to give the title compound (84.5%)1HNMR (400 MHz, DMSO-d6): 11.64 (s, 1H) 10.26 (s, 1H) 8.78 (s, 1H) 8.45 (s, 1H) 7.78 (s, 2H) 7.72 (d, 1H) 6.31 (d, 1H).MS (ESI+) m/z 310 [M+H]+

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 486424-37-7.

Reference:
Patent; ASTRAZENECA AB; US2011/118275; (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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H11BrN2O3

EXAMPLE 5 r3-(2.2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acidThe title compound was prepared according to the procedure shown below and described in details thereinafter.n-Butanol (2919.6 g, 3.6 I), 3-bromo-6-methyl-2-oxo-2(2H-pyrazine acetic acid) ethyl ester (Reagent (A) 600 g, 2.14 mol 1 equiv.)), and 2,2- difluoro-2-phenylethylamine (Reagent (B) 675 g, 4.29 mol, 2.00 equiv.) were charged to the reaction vessel and the reaction mixture heated to reflux. The reaction mixture was maintained at reflux. The reaction was then cooled to 750C and a 25% solution of sodium hydroxide (759 g, 600 ml 2.68 equiv.) was added. The reaction mixture was stirred at 750C. A 22% hydrochloric acid solution (1010 g, 900 ml, 3.13 equiv.) was then added slowly to the reaction mixture. The reaction mixture was allowed to cool to room temperature and then stirred overnight. The next morning the reaction mixture was cooled to 1 O0C, filtered, the filtrate washed with n-butanol (2.1 I), and then dried at 550C to yield the title compound as a residue.

According to the analysis of related databases, 221136-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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.

EXAMPLE 25 Step 1. 2-iodo-5-methoxy-pyrazine. Sodium methoxide (25% wt. in MeOH,0.321 mL, 1.4 mmol) was combined with N-methyi pyrrolidine (NMP) (1.28 mL) and warmed to 60 C. 2-bromo-5-iodo-pyrazine (0.40 g, 1.4 mmol) was added. The suspension was stirred at 60 0C for 1 hour. Combined with an additional 100 mg previously run reaction prior to work-up. Reaction mixture was partitioned between H2O and ethyl acetate and the aqueous layer was extracted (3x) with ethyl acetate. The combined extracts were dried over MgSO4, filtered and concentrated to give a brown oil which solidified to obtain 406 mgs of crude material. 1H NMR (400 MHz, CHLOROFORM-d) d ppm 3.90 (s, 3 H), 8.03 (d, J=1.4 Hz, 1 H), 8.29 (d, J=1.4 Hz, 1 H); MS (APCI+, m/z) 237.

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; PFIZER PRODUCTS INC.; WO2007/72151; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 143591-61-1, name is 3-Bromo-8-chloroimidazo[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 143591-61-1, SDS of cas: 143591-61-1

A mixture of compound 102 (2.00 g, 8.6 mmol), conc. aqueous NH4OH (60 mL) and 2-propanol (6 mL) was stirred in a closed pressure vessel at 85 C. for 3 days. The reaction mixture was cooled to 25 C., diluted with water (120 mL) and stirred at 25 C. for 10 minutes. The resulting heterogeneous solution was filtered, the solid was washed with water (3×) and air dried overnight. This gave compound 108 as a beige solid 1.50 g (82%). 1H-NMR (400 MHz, DMSO-d6) delta 7.66 (s, 1H), 7.56 (d, 1H), 7.35 (d, 1H), 7.1 (bs, 2H).

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

Reference:
Patent; Schering Corporation; US2007/105864; (2007); 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. 91775-62-1, name is 3-Bromo-8-methoxyimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Quality Control of 3-Bromo-8-methoxyimidazo[1,2-a]pyrazine

To a degassed mixture of 3-bromo-8-methoxyimidazo[1,2a]pyrazine (1.4g, 6.2mmol), cyclopropylboronic acid (0.8g, 9.3 mmol) potassium phosphate (4.6g, 21.Smmol) in water (5m1) and toluene (30m1), was added Palladium(ii)acetate and tricyclohexyl phosphine. The resulting reaction mixture was stined at 90C for 12h. The reaction mixture was cooled and partitionedbetween ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel and 10- 30% EtOAc in hexane) to obtain 3-cyclopropyl-8-methoxyimidazo[ 1 ,2-a]pyrazine (1 .0g, 91%). ?H NMR (300 MHz,CDC13): oe 7.79 (d, J= 4.8 Hz, 1H), 7.41 (d, J= 4.8 Hz, 1H), 7.33 (s, 1H),4.13 (s, 3H),1.84 – 1.83 (m, 1H), 1.07 – 1.02(m, 2H) 0.77 – 0.73(m,2H); LC-MS: 190.3 [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; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; KOTRABASAIAH UJJINAMATADA, Ravi; PANDIT, Chetan; (152 pag.)WO2016/185342; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem