Month: August 2021

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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-aminopyrazine-3-carboxylate

1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65C for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65C for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10% sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88%) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid.LCMS (EI, m/z): (M+l) 2801H NMR: 6H ppm (400 MHz, DMSO): 8.50 (1H, s, CHarom), 7.50 (2H, bs, NH2), 3.20 (3H, s, CH3).

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; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; KRUCZYNSKI, Anna; SCHMITT, Philippe; PEREZ, Michel; RAHIER, Nicolas; WO2012/101239; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 768-05-8,Some common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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: 2.3. General procedure for the synthesis of N’-(2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)pyrazine-2-carbohydrazide(8-14)The quest for the synthesis of N’-(2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)pyrazine-2-carbohydrazide (8-14) wasaccomplished in two steps as outlined in Scheme 1. A mixture of2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one (1-7) (1 mmol),commercially available pyrazine-2-carbohydrazide (PZH)(1.5 mmol) in methanol and chloroform mixture (1:1 v/v), andcatalytic amount of acetic acid (0.1 mL) was added and refluxed for2-3 h. On the completion of reaction, a solid mass was formed.After cooling to room temperature, the precipitate was filtered offand washed with cold mixture of ethanol and water. The crude product was recrystallized from ethanol [16].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazinoic acid hydrazide, its application will become more common.

Reference:
Article; Mangalam; Sebastian Antony Selvan; Sankar; Journal of Molecular Structure; vol. 1129; (2017); p. 305 – 312;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 914452-71-4, 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. 914452-71-4 name is 2-Bromo-6-methylpyrazine, 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.

To a solution of 2-bromo-6-methyl-pyrazine 53-3 (875.52 mg, 5.06mmol) and methyl 1- chloropiperidine-4-carboxylate 53-2 (1000 mg, 5.57mmoi) in toluene (25 mL) was added cesium carbonate (4.95 g, 15.18 mmol). The reaction was degassed with argon for 10 minutes. Xanthphos (146.40 mg, 253.03 umol) and Pd2(dba>3 (231.70 mg, 253.03 umol) were added and the mixture was heated at 90C for 16 hours. The reaction was then cooled to room temperature and diluted with ethyl acetate. Organic layer was washed with water and brine, dried over sodium sulfate, concentrated under reduced pressure, and purified by combiflash chromatography (eluting with 2 % methanol in dichi orom ethane) to afford methyl l-(6-methylpyrazin-2-yl)piperidine-4- carboxylate 53-4 (750 rng, 3.19 mmol, 62 99% yield) as brown solid. LC MS: ES+ 235.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-6-methylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-29-5, The chemical industry reduces the impact on the environment during synthesis 33332-29-5, name is 2-Amino-5-chloropyrazine, I believe this compound will play a more active role in future production and life.

Example 776-chloro-2-[3-nitro-4-(trifluoromethyl)phenyllimidazo[1 ,2-alpyrazineA solution of 5-chloropyrazin-2-amine (0.336 g, 2.6 mmol) and 2-bromo-1 -[3-nitro-4- (trifluoromethyl)phenyl]ethanone (0.81 1 g, 2.6 mmol) in acetonitrile (15 mL) is stirred at 100 C for 18 hr. The mixture is concentrated to give the title compound (890 mg), which is used without further purification. LCMS m/z = 343.3 [M+H]+, fR = 2.65 min.

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-Amino-5-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PAMLICO PHARMACEUTICAL INC.; ATKINSON, Robert N.; OMMEN, Andy J.; VEAL, James M.; HUANG, Kenneth H.; SMITH, Emilie, D.; WO2012/88411; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 59303-10-5, 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 59303-10-5 as follows.

Example 192-(2-Methyl-imidazol-1 -yl)-pyrimidine-5-carboxylic acid cvclopropyl-H -(5-methyl- pyrazin-2-yl)-pipehdin-4-vH-amideA mixture of 2-(2-methyl-imidazol-1 -yl)-pyrimidine-5-carboxylic acid cyclopropyl- piperidin-4-yl-amide (44 mg, Intermediate 20), 2-chloro-5-methylpyrazine (15 mg) and ethyldiisopropylamine (35 muIota_) in N-methyl-2-pyrrolidinone (1 .0 ml_) is heated in a microwave oven for 30 min at 200C. After removal of the solvent the residue is purified by HPLC (H2O/MeOH/TFA) to give the title compound. LC (method 3): tR = 0.92 min; Mass spectrum (ESI+): m/z = 419 [M+H]+.

According to the analysis of related databases, 59303-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products 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.

General procedure: To a solution of 2a-j (10 mmol, 1.0 eq) , 3,5-dibromo-1-methylpyrazin-2(1H)-one (2.95 g, 11 mmol, 1.1 eq) and DIEA (3.3 mL,20 mmol, 2.0 eq) in MeCN (20mL) was stirred at 80 °C for 5 hours. After cooling to room temperature, thesolvent was removed in vacuo, and the residue was purified using silica gelchromatography to give the title compounds, yield 72-85percent.

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:
Article; Yang, Jianhong; Du, Jiatian; Huang, Chong; Wang, Tianqi; Huang, Luyi; Yang, Shengyong; Li, Linli; Bioorganic and Medicinal Chemistry Letters; vol. 29; 13; (2019); p. 1609 – 1613;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 117103-53-4, name is 2-Bromo-5-nitropyrazine, 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 117103-53-4, Safety of 2-Bromo-5-nitropyrazine

Example 72 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N- [5- (2-METHOXY- ethylamino)-pyrazin-2-yl]-propionamide [000336] A mixture of 2-bromo-5-nitropyrazine (500 mg, 2.45 mmol) and 2- METHOXYETHYLAMINE (276 mg, 3.67 mmol) in methanol (15 ML) was stirred at 25C for 5 h. After such time, the reaction was concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 40/60 to 20/80 hexanes/ethyl acetate) afforded (2-methoxy-ethyl)- (5-nitro-pyrazin-2-yl) -amine (291 mg, 60%) as a yellow solid: mp 116.0-117. 3C ; EI- HRMS m/e calcd for C7HLON403 (M+) 198.0753, found 198. 0751.

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; WO2004/52869; (2004); 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. 5521-56-2, name is 6-Methylpyrazin-2-amine, A new synthetic method of this compound is introduced below., Formula: C5H7N3

Step 5: 5-bromo-6-methylpyrazin-2-amine A 10-L, 4-necked round-bottom flask was charged with 6-methylpyrazin-2-amine (590 g, 5.4lmol, 1.00 equiv), chloroform (7 L) and NBS (960 g, 5.39 mol, 1.29 equiv). The reaction mixture was stirred for 12 h at room temperature. The resulting solid was filtered out and the filtrate was concentrated under vacuum to give the title compound, which was used in the next step without further purification.

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 SHARP & DOHME CORP.; COLLETTI, Steven, L.; DEMONG, Duane; DYKSTRA, Kevin, D.; HU, Zhiyong; MILLER, Michael; (104 pag.)WO2019/99315; (2019); 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: (3-Chloropyrazin-2-yl)methanamine hydrochloride

(b). (S)-benzyl 2-((3-chloropyrazin-2-yl)methylcarbamoyl)pyrrolidine-1-carboxylate was prepared as follows. To a solution of (3-chloropyrazin-2-yl)methanamine HCI (9.57 g, 21.26 mmol, 40% wt) and Z-Pro-OH (5.3 g, 21.26 mmol) in dichloromethane (250 mL) was added triethylamine (11.85 mL, 85 mmol) and the reaction mixture was cooled to 0C. After 15 min stirring at 0C, HATU (8.49 g, 22.33 mmol) was added. The mixture was stirred for 1 hour at 0C and then overnight at room temperature. The mixture was washed with 0.1 M HCI- solution, 5% NaHC03, water and brine, dried over sodium sulfate and concentrated in vacuo. The product was purified using silica gel chromatography (heptane/ethyl acetate = 1/4 v/v%) to give 5 g of (S)-benzyl 2-((3-chloropyrazin-2-yl)methylcarbamoyl)pyrrolidine-1-carboxylate (62.7%).

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; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (268 pag.)WO2016/24227; (2016); 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C6H9N3

To a solution of 2-bromo-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5- carboxamide (0.25 g, 0.61 mmol) and 5,6,7,8-tetrahydroimidazo[1 ,2-a]pyrazine (0.09 g, 0.74 mmol) in dioxane (5 ml_), NaOtBu (0.09 g, 0.92 mmol) and RuPhos (0.06 g, 0.12 mmol) were added. The reaction mixture was purged with argon for 20 min followed by addition of Pd2(dba)3 (0.06 g, 0.06 mmol). The reaction mixture was heated at 1 10C for 6h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with H20 (70 mL) and extracted with EtOAc (3 x 100 mL). The organic layer was separated, washed with brine (75 mL), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 230-400 mesh, 0 to 6% MeOH in DCM) and preparative HPLC to afford 2-(6,8-dihydro-5H-imidazo[1 ,2-a]pyrazin-7-yl)-N-[1- (1 H-indol-3-ylmethyl)pentyl]thiazole-5-carboxamide (0.06 g, 19%) as an off- white solid. HPLC Purity: 98.7% MS (ESI) m/e [M+H]+/Rt %: 449.00/2.24/99.2% 1H NMR (400 MHz, DMSO-d6) delta 0.81 (t, J=6.85 Hz, 3H) 1.16 – 1.30 (m, 4H) 1.47 – 1.62 (m, 2H) 2.78-2.94 (m, 2H) 3.92-3.98 (m, 2H) 4.04-4.14 (m, 3H) 4.66 (s, 2H) 6.91 (s, 1 H) 6.95 (d, J=7.34 Hz, 1 H) 7.03 (t, J=7.58 Hz, 1 H) 7.09 (brs, 1 H) 7.14 (s, 1 H) 7.30 (d, J=7.83 Hz, 1 H) 7.56 (d, J=7.83 Hz, 1 H) 7.86 (s, 1 H) 8.01 (d, J=8.31 Hz, 1 H) 10.74 (brs, 1 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; UCB BIOPHARMA SPRL; HALL, Adrian; PROVINS, Laurent; MACCOSS, Malcolm; (72 pag.)WO2018/138088; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem