Tag: M.W=200-300

These common heterocyclic compound, 1458-16-8, name is Methyl 3-amino-6-iodopyrazine-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. category: Pyrazines

Example 3b: 3-amino-6-iodopyrazine-2-carboxamide 30 ml of ammonia in water is added under magnetic stirring to 15 g (53.8 mmol) of a solution of methyl 3-amino-6-iodopyrazine-2-carboxylate in 150 ml of methanol. The reaction medium is stirred at 25C for 48 hours. After evaporation of the solvents, the precipitate obtained is filtered, rinsed with water and then dried at 50C to yield 12.50 g of 3-amino-6-iodopyrazine-2-carboxamide (88%) in the form of a beige solid. LCMS (EI, m/z): (M+l) 265.02 1H NMR: deltaEta ppm (400 MHz, DMSO): 8.35 (1H, s, CHarom), 7.85 (1H, bs, NH), 7.60 (3H, bs, NH), 3.25 (3H, s, CH3).

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

Reference:
Patent; PIERRE FABRE MEDICAMENT; SOKOLOFF, Pierre; CACHOUX, Frederic; WO2014/16433; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9, 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 6,8-dibromoimidazo[1,2-a]pyrazine (6, 1.86 g, 6.72 mmol) was added to asolution of 3a-3c, 5a-5e (5.6 mmol), DIPEA (1.4 mL, 8.4 mmol) inisopropanol (60 mL), stirred at 85 C for 8 h, and then the solvent wasevaporated to dryness. The crude product was purified by columnchromatography to obtain the desired intermediates 7a, 11a-11 g.

The synthetic route of 6,8-Dibromoimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fan, Yan; Huang, Zhi; Li, Yao; Qin, Zhongxiang; Wang, Cheng; Wang, Tianqi; Wang, Xin; Xiang, Rong; Yang, Shengyong; Bioorganic Chemistry; vol. 95; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 622392-04-5, name is 2-Bromo-5-iodopyrazine, 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 622392-04-5, Recommanded Product: 2-Bromo-5-iodopyrazine

Preparation 62: Methyl {(2S)-1 -[(2S)-2-{4-[4-(5-bromopyrazin-2-yl)phenyl]-1 H-imidazol-2-yl}pyrrolidin- 1 -yl]-3-methyl-1 -oxobutan-2- l}carbamateMethod A:To a solution of methyl {(2S)-3-methyl-1-oxo-1-[(2S)-2-{4-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl]-1 H-imidazol-2-yl}pyrrolidin-1-yl]butan-2-yl}carbamate obtained from Preparation 61 (33.00 g, 66.53 mmol) and 2-bromo-5-iodopyrazine obtained from Preparation 10 (24.70 g, 86.67 mmol) in 1 ,4- dioxane (600 mL) and water (150 mL), were added potassium phosphate (28.20 g, 133.01 mmol) and tetrakis(triphenylphosphine)palladium (0) (2.30 g, 1.99 mmol). The mixture was sparged with nitrogen for 10 minutes before heating to reflux for 16 hours. After this time, the reaction was allowed to cool to room temperature, the solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (250 mL) and water (250 mL). The layers were separated and the organic layer was washed with brine (500 mL), dried over magnesium sulphate. The solvent was removed under reduced pressure to give a black gum. The crude product was purified by flash chromatography (heptane : acetone, 20:80) to give the title compound as a foam ( 22.00 g).LCMS (run time = 25 minutes, System K) Rt= 13.19; m/z 527 and 529 [MH+]H NMR (400 MHz, CD3OD+drop of TFA) : delta= 8.99 (s, 1 H), 8.81 (s, 1 H), 8.25 (d, 2H), 7.94 (s, 1 H) 7.86 (d, 2H), 5.27-5.23 (m, 1 H), 4.24 (d, 1 H), 4.13-4.08 (m, 1 H), 3.88 (m, 1 H), 3.65 (s, 3H), 2.62-2.54 (m, 1 H), 2.31- 2.24 (m, 1 H), 2.20-2.14 (m, 2H), 2.09-2.00 (m, 1 H), 0.93 (d, 3H), 0.88 (d, 3H).

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-Bromo-5-iodopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; TRAN, Thien Duc; WAKENHUT, Florian; WO2011/154871; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 21943-17-9,Some common heterocyclic compound, 21943-17-9, name is 5-Bromo-3-chloropyrazin-2(1H)-one, molecular formula is C4H2BrClN2O, 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: A solution of 56 (1.50 g, 7.16 mmol), the appropriate secondary amine (8.59 mmol, 1.20 equiv) and diisopropylethylamine (1.50 mL, 8.59 mmol) in n-butanol (15 mL)was heated in a microwave reactor using variable wattage to 140 C for 1 h. The mixture was concentrated and purified by flash column chromatography on silica, eluting with 9:1 dichloromethane/methanol, to give gave 58-63.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-3-chloropyrazin-2(1H)-one, its application will become more common.

Reference:
Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728,16;; ; Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728;,
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

3-Bromo-8-(methylthio)imidazo|”l,2-a”|pyrazine[00241] A solution of NaSMe (385 mg, 5.497 mmol) in DMSO (4 mL) was added to a solution of 3-bromo-8-bromo/chloroimidazo[l,2-a]pyrazine (1.015 g, 4.581 mmol) in DMSO (20 niL) and the resulting mixture was heated at 1000C for 16 hours. After cooling to room temperature, brine was added and the product then extracted into a DCM/isopropanol (9:1) mixture (3 times). The combined organic layers were washed with brine, dried (MgSO4) and purified by flash column chromatography (2:1, 40-60 petrol:EtOAc) to give the title compound (657 mg; 57%). 1H NMR (d6-DMSO): 8.17 (IH, d, J4.8), 7.91 (IH, d, J4.8), 7.84 (IH, s), 2.61 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 41270-66-0, 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. 41270-66-0 name is 5-Chloro-2,3-diphenylpyrazine, 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.

[123] Step 1. 2-(1.1.2.2.3.3.4.4-dg-4-((5.6-Diphenylpyrazin-2-yl)(propan-2-yl)amino)butan- l-ol (12b). To a solution of commercially available 5-chloro-2,3-diphenylpyrazine (10) (0.57 g, 2.14 mmol) in NMP (2.0 mL), was added d7-aminoalcohol lib (0.75 g, 5.35 mmol, 2.5 equiv, prepared as described in Example 10). The reaction vessel was sealed and heated to 190 0C for 15 hours, then cooled to ambient temperature. The mixture was diluted with ice water and extracted with Et2O (3 x 20 mL). The combined organic layers were washed successively with water and brine. The resulting organic layer was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 30-50% EtO Ac/heptane) to afford 12b (0.20 g, 25%). MS (M+H): 370.0

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

Reference:
Patent; CONCERT PHARMACEUTICALS, INC.; HARBESON, Scott L.; MASSE, Craig E.; LIU, Julie F.; WO2011/17612; (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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1196152-38-1

bis(triphenylphosphine)palladium(II) chloride (21.40 mg, 0.030 mmol), triphenylphosphine (15.99 mg, 0.061 mmol), TEA (4.5 ml, 32.3 mmol), 2-bromo-5-(trifluoromethyl)pyrazine (346 mg, 1.524 mmol) and copper(I) iodide (11.61 mg, 0.061 mmol) were collected together in a round bottomed flask. The mixture was stirred for 30 minutes and then 1,1- dimethylethyl (lR,4S,6R)-4-ethynyl-3-azabicyclo[4.1.0]heptane-3-carboxylate D5 (337 mg) was added. The reaction was stirred at room temperature for 2 hours.A saturated solution of H4CI (10 ml) was added and the aqueous layer was back extracted with diethyl ether (3 x 10 ml). The collected organic layers were washed with brine (3 x 5 ml), dried over Na2S04, filtered, and concentrated under vacuum to give the crude product. The crude product was purified by silica gel chromatography (SNAP KP-Sil 25g cartridge; eluted with Cy/EtOAc 5CV from 100% Cy to 90/10, 5 CV 90/10).Collection and evaporation of the fractions gave the title compound D27 (300 mg).UPLC (GEN_QC_SS) rt = 1.02 minutes, peak observed: 312 [M-C(CH3)3] Ci8H20F3N3O2 requires: 368.

According to the analysis of related databases, 1196152-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89607; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 762240-92-6, A common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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 the 1 OOgm(3R)-3- [(1,1 -dimethyl ethoxy carbonyl)amino}-4-(2,4,5-trifluorophenyl butanoic acid charged 700m1 methylenedichioride and 67gm triethylamineandstirred for 10 minutes.Added 68gmNN?-Dicyclohexylcarbodiimide, 44.6 gm of anhydrous 1 – hydroxylbenzotriazole and maintained for about 10-20 minutes.Added75.5gm 3- trifluromentyl 5,6,7,8-tetrahydro (1 ,2,4) triazolo[4,3-a] pyrazineHCl and heated to 25- 30C and maintained for 4 hours. After completion of reaction,filtered the reaction mass and filtrate was washed with 2x350m1 2.5%sodium bicarbonate solutionandwashed with 2x500m1 of water.MDC layer was taken without purification and Cooled to 0-10C.400m1 1 6%Methanolic HCI added and raised the temperature to 25-30C and Stirred for 4 hours.After completion of the reaction added 1000m1 water and separatedlayers.ExtractedtheMDClayer with 2x300m1 DM water.Aqueous layer was washed with 300m1 MDC and pH of the aqueous layer was adjusted to 10-1 1%with 1 0%sodium hydroxide solution. 1 000m1 MDC charged and Stirred for I 0mm. The organic layer separated and the Aq layer was extracted twice with 300 ml MDC. The organic layer was separated and washed with 300 ml of water followed by 300m1 5% NaCl; and driedthe organic layer with anhydrous sodium sulfate. The organic layer separated and the solvent was distilled out under vacuum. 1 OOm1IPA was added to residue and again distilled under vacuum followed by addition of 800m1 heptane. Filtered the crystallized Material and dried under vacuum at 50C for 12-15 hours to get 96.5% titled compound.BPLC purity:99-99.9% Chiral purity: 99.9%

The synthetic route of 762240-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HARMAN FINOCHEM LIMITED; KADAM, Vijay, Trimbak; SARANAPU, Nareesh; SINGAMPALLI, Sri, Hari; MINHAS, Harpreet, Singh; MINHAS, Gurpreet, Singh; (16 pag.)WO2017/6335; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 762240-92-6 as follows. name: 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

At room temperature, compound I22.8g (100mmol), bromoacetyl chloride 31.2g (200mmol) and cesium carbonate 65.2g (200mmol) were added to the flask in 100mL DMF and stirred for 3h at room temperature; after the reaction was completed, ethyl acetate was extracted The organic phase was concentrated, washed with water, and then recrystallized from ethanol, and dried to obtain 28.4 g of compound II in a yield of 91%.

According to the analysis of related databases, 762240-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Qike Pharmaceutical Co., Ltd.; Yang Bo; Chen Yao; (11 pag.)CN110577542; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1379338-74-5, A common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, molecular formula is C7H3Cl2N3, 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.

Intermediate 32: 1,1-Dimethylethyl {4-[(7-chloropyrido[3,4-b]pyrazin-5-yl)amino]butyl}carbamate To 5,7-dichloropyrido[3,4-b]pyrazine (650 mg, 3.25 mmol) was added 1,1-dimethylethyl (4-aminobutyl)carbamate (0.622 ml, 3.25 mmol) (Fluka) and diisopropylethylamine (0.851 ml, 4.87 mmol). To the mixture was added N-methyl-2-pyrrolidone (NMP) (10 ml). The microwave vial was sealed and heated to 130 C. for 30 min. The reaction mixture was partitioned between water (70 ml) and ethyl acetate (70 ml) and then separated. The aqueous layer was extracted with ethyl acetate (2*50 ml). The combined organics were passed through a phase separation cartridge and reduced in vacuo. The residue was dissolved in DCM and loaded onto a silica cartridge (50 g) and purified via SP4 using a 15-75% EtOAc in cyclohexane gradient. The appropriate fractions were combined and concentrated to give the title compound as a yellow film (1.01 g). LCMS (Method C): Rt=1.11 min, MH+=352.0

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; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Atkinson, Stephen John; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander G.; Shipley, Tracy Jane; Wilson, David Matthew; Watson, Robert J.; US2014/5188; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem