Tag: M.W=100-200

Application of 23688-89-3, 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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

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, 6-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 98-97-5, 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. 98-97-5, name is Pyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

? Charged MeOH (8.8 L) and OT-1 (1758 g) at RT. (0129) ? Charged H2S04 (69.5 g) in one portion (21-22 C exotherm). Heated to (60-65 C) and stirred at 55-65 C for 19 hours. (0130) 19 h, 96.0% OT-2 and 4.0% OT-1 by HPLC (0131) ? Reaction was cooled to 15/30 C. No precipitate formed. (0132) ? NaHC03 (180 g) was charged in lots. The solution bubbled slightly and quickly went from yellow to pink. The mixture was stirred for 5 min at 15/30 C. (0133) ? The mixture was then concentrated to 1.5-2.5 vol at (0134) ? Charged NaCl (.700 g) in water (2.5 vol). Upon stirring, solution became clear. (0135) ? Stirred for 15 min at 15/30 C. After stirring, the aqueous layer became slightly cloudy. The solids were filtered off and the layers were separated. (0136) ? The aqueous layer was extracted with DCM (3×2 vol.). TLC indicated that extraction was complete after 3rd extraction. (0137) ? Organic layers were dried over anhydrous Na2S04 (.4g/g SM) . (0138) ? Concentrated to 1.5-2.5 vol under vacuum at (0139) ? Charged heptanes (8 vol) over a minimum of 30 min. Pale white slurry. Let stir overnight. ? Stirred at -5/- 15 C for a minimum of 1 hr. Solids were filtered off and rinsed with cold heptanes (0140) ? (2×1 vol.) Pulled solids dry on filter for 10 min. Dried in vacuum oven at (0141) Color changed, but no degradation was observed . (0142) Output material: ST-601 (0143) Lot No.: 2463-24- 1 (0144) Appearance: light Brown Solids (0145) Yield: 1721 g (91.0%) (0146) HPLC purity: 98.9% (0147) 1 NMR- Conforms to structure

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, Pyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ST IP HOLDING AG; FRAMROZE, Bomi P.; (65 pag.)WO2016/207914; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, 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: (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

Step B – Syntheses of Intermediate Compound Int-31b (0407) (0408) To a -78 °C solution of (2R)-(-)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (0.61 g, 4.36 mmol) in THF (8 mL) was added n-BuLi (2.5 M in hexane, 1.8 mL, 4.58 mmol). The resulting reaction was allowed to stir for 20 minutes, then Compound Int-31a (2.75 g, 6.98 mmol, in 2 mL of THF) was added and the reaction was allowed to stir at -78 °C for 4 hours. The reaction was quenched with saturated aqueous NH4Cl solution and the organic layers were extracted with EtOAc. The combined organic solution was washed with brine solution, dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified using an ISCO 40 g column (gradient from 0percent to 2.5percent ether in hexane) to provide Compound Int-31b, 783 mg (44percent). 1H NMR (CDCl3) delta 4.05 (m, 1H), 3.96 (t, J = 3.4 Hz, 1H), 3.72 (s, 3H), 3.71 (s, 3H), 3.49 (dd, J = 2,8, 0.4 Hz, 1H), 3.26 (dd, J = 6, 9.4 Hz, 1H), 2.30 (m, 1H), 1.96 (m, 1H), 1.60 (m, 2H), 1.37-1.17 (m, 3H), 1.08 (d, J = 6.9 Hz, 3H), 0.99-0.86 (m, 2H), 0.72 (d, J = 6.6 Hz, 3H), 0.49 (dd, J = 11.0, 14.4 Hz, 1H), 0.35 (dd, J = 11.0, 14.2 Hz, 1H), 0.16 (s, 6H).

The synthetic route of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Nair, Anilkumar Gopinadhan; Keertikar, Kerry M.; Kim, Seong Heon; Kozlowski, Joseph A.; Rosenblum, Stuart; Selyutin, Oleg B.; Wong, Michael; Yu, Wensheng; Zeng, Qingbei; EP2545060; (2015); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5521-55-1, 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. 5521-55-1 name is 5-Methylpyrazine-2-carboxylic acid, 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.

The reaction was carried out, under nitrogen, in a 1 L×4 neck flask equipped with a mechanical stirrer, water condenser (with gas inlet), and a thermocouple. The reactor was charged with 5-methylpyrazinecarboxylic acid (100 g), AMBERLYST 15 ion exchange resin (20 g), and methanol (300 g). The mixture was stirred at reflux for about 20 h. After the reaction was complete (analyze with GC or GC/MS), the resin was removed by pressure filtration. The resin was rinsed with methanol and about 75% of the solvent was removed under reduced pressure. The resulting suspension was allowed to stand at room temperature overnight, and then in an ice-bath for 3 h. The solid was collected by filtration and washed with ice-cold methanol (2×80 g). Drying under vacuum at room temperature (25 inches of Hg) yielded 102.4 g (93%) of 5-methyl-2-pyrazonecarboxylic acid, methyl ester that was suitable for further use.

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

Reference:
Patent; ISP INVESTMENTS INC.; US2005/261312; (2005); 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. 123-32-0, name is 2,5-Dimethylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 123-32-0

2,5-Dimethylpyrazine (0.99 g, 9.15 mmol), benzaldehyde( 4.00 mL, 39.4 mmol) and benzoic anhydride (4.97 g,22.0 mmol) were stirred in a microwave tube until full dissolution occurred. Argon was bubbled through the yellow mixture and was reacted at 175 C in the microwave for 5 h,with rapid stirring. After cooling, a dark brown solid was obtained, which was suspended in cold ethanol before filtering and washing with cold ethanol to yield a yellow crystalline solid (1.61 g, 5.7 mmol, 62%). This product was carriedthrough to the next reaction without further purification. 1HNMR (500 MHz, CDCl3):delta 8.60 (2H, s, ArH), 7.74 (2H, d,J = 16 Hz, CH), 7.63-7.59 (4H, m, ArH), 7.43-7.31 (6H, m,ArH), 7.19 (2H, d, J = 16 Hz, CH).

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 123-32-0.

Reference:
Article; Dais, Tyson N.; Brown, Michael J.; Coles, Martyn P.; Laur, Francois; Price, Jason R.; Rowlands, Gareth J.; Plieger, Paul G.; Journal of Inclusion Phenomena and Macrocyclic Chemistry; vol. 94; 3-4; (2019); p. 175 – 182;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 109838-85-9, These common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, 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 5 L- 3 necked round bottomed flask, equipped with a mechanical stirrer, temperature probe, addition funnel and N2 inlet, was charged with the Schollkopf chiral auxiliary-(Int-13a, 200 g, 1.09 mol, 1.0 eq), bis(chloromethyl) dimethylsilane (Int-13b, 256 g, 1.63 mol, 1.5 eq), and THF (2 L, Aldrich anhydrous). The flask was cooled in a dry ice/ 2- propanol bath until the internal temperature reached -75 °C. n-Butyllithium (Aldrich 2.5 M in hexanes , 478 mL, 1.19 mol, 1.09 eq) was added via a dropping funnel over 1 hour while maintaining the internal reaction temperature between -67 °C and -76 °C. The resulting orange-red solution was allowed to gradually warm to room temperature for about 15 hours. The reaction mixture was then re-cooled to 0 °C and quenched with 500 mL of water.Diethyl ether (2L) was added and the layers were separated. The aqueous layer was extracted with 1 L of diethyl ether. The combined organic extracts was washed with water and brine, dried with MgS04, filtered, and concentrated in vacuo to dryness, giving 480 g of orange oil. This material was left in vacuo for about 15 hours to provide 420 g of oil. The crude product was split into two batches and purified via silica gel chromatography on a 1.6 kg flash column. The column was eluted with gradient of 0-4percent Et20 in hexanes. The product fractions were concentrated in vacuo at a bath temperature at or below 40 °C giving 190 grams of Int-13c-(60percentyield).

The synthetic route of 109838-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; COBURN, Craig, A.; LAVEY, Brian, J.; DWYER, Michael, P.; KOZLOWSKI, Joseph, A.; ROSENBLUM, Stuart, B.; WO2012/50848; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 123-32-0, A common heterocyclic compound, 123-32-0, name is 2,5-Dimethylpyrazine, molecular formula is C6H8N2, 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.

2,5-dimethylpyrazine (0.5 g, 0.00462 mol) and 1-methylpyr-role-2-carboxaldehyde (1.513 g, 0.0138 mol) were dissolved in DMFand the mixture was cooled to 0 C (Scheme 1). To this mixture,potassium-tert-butanolate (1.55 g, 0.013 mol) were added in smallportions and the mixture was brought to ambient temperature andstirring was continued until all starting material had beenconsumed (TLC). After the completion of the reaction, waterwas added, and the product was isolated by extraction withchloroform. The organic layer was concentrated in vacuum and thesolid material obtained was recrystallized to give the product(1.2 g, 42%) as an orange solid. The structure of the compound wasconfirmed by IR and 1H and 13C NMR techniques.1H NMR (CDCl3, 500 MHz): delta = 3.7 (s, 6H), 6.16 (m, 2H), 6.64 (m,2H), 6.72 (m, 2H), 6.86 (d, 2H, J = 15.4 Hz), 7.60 (d, 2H, J = 15.4 Hz),8.42 (s,2H). 13C NMR (CDCl3, 150 MHz): delta = 34.2, 107.9, 108.2, 119.3,120.6, 122.1, 128.5, 140.1, 147.8.

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:
Article; El-Daly, Samy A.; Asiri, Abdullah M.; Alamry, Khalid A.; Osman, Osman I.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 312; (2015); p. 64 – 72;,
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. 54608-52-5, name is 2-Hydrazinopyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 54608-52-5

To a mixture of 2.38 g (21.6 mmol) of 2-hydrazinopyrazine and 2.41 g (3.32 mL, 23.8 mmol) of triethylamine in 50 mL of acetonitrile was added 3.25 g (2.66 mL, 23.8 mmol) of ethyl chloro (oxo) acetate at 0 C. The reaction mixture was stirred at ambient temperature for 18 h, and then partitioned between aqueous sodium bicarbonate solution and ethyl acetate. The aqueous phase was extracted with three portions of ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, and concentrated to give the title compound. LC/MS 211 (M+1).

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; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486460-21-3,Some common heterocyclic compound, 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C6H7F3N4, 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 solution of (R) -3- [N- (tert- butoxycarbony1) amino] -4- (2, 4, 5-trifluoro-phenyl) butanoic acid ( 0.333 g, lmmol) of Example 8 and 3- ( trif luoromethyl- 5, 6, 7, 8-tetrahydro-l, 2, 4-triazolo [4, 3a] pyrozine (0.192 g, 1 mmol) in DMF (12 ml) was added HOBT (0.162 g, 1.2mmol) and EDC (0.230 g. 1.2 mmol) at 0 0C. After being stirred at room temperature for 16 h, DMF was evaporated and the residue extracted with ethyl acetate (3 X 20 ml) . The organic extracts were washed with NaHSO4 aq, then NaHCO3, then brine, and then dried over Na2SO4. Concentration was followed by purification by flash chromatography to afford 0.375 g of the title compound (71.8%) . 1H NMR (300 MHz, CDCl3) 7.10-7.00 (m, IH), 7.00-6.90 (m, IH), 5.25-5.35 (br, IH), 5.10-5.00 (m, IH), 4.90 (s, IH), 4.30-3.90 (m, 5H), 3.00-2.90 (m, 2H), 2.80-2.60 (m, 2H), 1.35 (s, 9H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, its application will become more common.

Reference:
Patent; CHIRAL QUEST, INC.; WU, Shulin; YU, Bo; WANG, Yejing; DELICE, Alain; ZHU, Jingyang; WO2010/78440; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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. Recommanded Product: 875781-43-4

A.1. Synthesis of lM-1A.1.1. Experimental procedure for the synthesis of IM-1SM-1 SM-5a IM-1a2-Bromo-5/-/-pyrrolo[2,3- 5]pyrazine SM-1 (500 mg, 2.5 mmol), 1-Boc-4-(methylamino)- piperidine SM-5a (1.082 g, 5.0 mmol), Pd2(dba)3 (139 mg, 0.1 mmol), DavePhos (238 mg, 0.6 mmol) and LiHMDS (12.625 mL, 12 mmol) are taken-up in dry THF (10 mL) and the resulting mixture is flushed with Argon and stirred for 1 h at 80 C. The reaction mixture is diluted with H20 and AcCN, Isolute is added, the solvent is removed in vacuo and the residue is purified via RP HPLC. The product containing fractions of IM-1 a (HPLC-MS method A: tRet. = 1.72 min; MS (M+H)+ = 332) are freeze dried.

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STADTMUELLER, Heinz; WO2012/104388; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem