Month: June 2021

Reference of 54608-52-5,Some common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, molecular formula is C4H6N4, 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 mixture of amidrazone 1a (1.00 g, 0.0047 mol), benzaldehyde (2a)(0.50 g, 0.0047 mol), PEG-300 (5 mL) and CAN (5 mol%) was heated at 80 C for 1 h (Table 2). After completion of the reaction as monitored by TLC, the mixture was cooled to r.t. and extracted with Et2O (3 × 20mL). The combined organic layers were washed with H2O (2 × 30 mL) and aq NaHCO3 solution (2 × 30 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (EtOAc-hexane, 1:1) to afford pure 3a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Hydrazinopyrazine, its application will become more common.

Reference:
Article; Nakka, Mangarao; Tadikonda, Ramu; Rayavarapu, Srinuvasarao; Sarakula, Prasanthi; Vidavalur, Siddaiah; Synthesis; vol. 47; 4; (2015); p. 517 – 525;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4949-13-7, 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 4949-13-7 as follows.

(6-chloropyridin-2-yl)(3-fluoropyrazin-2-yl)methanone2,2,6,6-tetramethylpiperidine (1.729 g, 2.066 mL, 12.24 mmol) was dissolved in THF (20.00 mL) and cooled to -30 C under nitrogen. BuLi (4.488 mL of 2.5 M, 1 1.22 mmol) was added dropwise and the reaction allowed to warm to 0 C. Stir at this temperature for 10 minutes then cooled to -78 C. A solution of 2-fluoropyrazine (1 g, 10.20 mmol) in THF (4.000 mL) was added slowly and the mixture stirred at -78 C for lh. Methyl 6-chloropyridine-2-carboxylate (1.750 g, 10.20 mmol) in THF (6.000 mL) was added dropwise at between -78 and -70C, stirred at -78C for lh. Reaction quenched with 5% citric acid at -78 C then allow to warm to ambient temperature. Diluted with EtOAc and separated layers. Extracted with EtOAc (xl) then wash combined organics with aHCOs (xl), brine (xl). Dried (MgS04), filtered and concentrated. Crude product purified by ISCO companion (80 g S1O2, 0 to 50% EtO Ac/petrol) to leave title compound as an orange oil (1.12g, 46%). ¾ NMR (DMSO-d6) delta 7.90 (dd, 1H), 8.22 – 8.15 (dd, 2H), 8.67 (dd, 1H), 8.84 (dd, 1H). ES+ 238.13.

According to the analysis of related databases, 4949-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; JIMENEZ, Juan-Miguel; SETTIMO, Luca; FRAYSSE, Damien; BRENCHLEY, Guy; DAVIS, John, Christopher; MILLER, Andrew, W.; WO2011/94288; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1245644-42-1, 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 1245644-42-1 as follows.

To a solution of 6-bromo-3-iodoimidazo[1,2-a]pyrazine (3.00 g, 9.26 mmol) in DMF (20 mL), was added Na2CO3 (2.46 g, 23.2 mmol), 4-chlorophenylboronic acid (1.60 g, 10.2 mmol) and Pd(PPh3)4 (214 mg, 0.18 mmol). The resulting mixture was stirred at 80 C. for 18 h under inert atmosphere and was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent Hex/EtOAc 3:2) to afford 6-bromo-3-(4-chlorophenyl)imidazo[1,2-a]pyrazine (930 mg, 32%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.03 (d, J=1.2 Hz, 1H), 8.36 (d, J=1.2 Hz, 1H), 7.91 (s, 1H), 7.54 (q, J=12.3 Hz, 4H); MS (ESI) m/z 308 [C13H7BrN4+H]+.

According to the analysis of related databases, 1245644-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 27398-39-6, The chemical industry reduces the impact on the environment during synthesis 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

Intermediate Y 3-(Pyridin-2-yl)pyrazine-2-carboxylic acid Step 1 : methyl 3-chloropyrazine-2-carboxylate (YD To a solution of 3-chloropyrazine-2-carboxylic acid (100 mg, 0.63 mmol) in DCM/MeOH (2 mL : 0.2 mL) was added TMSCHN2 (0.47 mL, 0.95 mmol) at RT and the resulting mixture was stirred at RT for 2 h. Acetic acid (0.2 mL) was added and the mixture was diluted with water (2 mL) and extracted with DCM (4 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo to give the title compound. LRMS m/z (M+H) 173.0 found, 173.0 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (116 pag.)WO2016/100161; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4774-14-5, The chemical industry reduces the impact on the environment during synthesis 4774-14-5, name is 2,6-Dichloropyrazine, I believe this compound will play a more active role in future production and life.

To a mixture of 2,6-dichloropyrazine (11.0 g, 73.8 mmol) and formamide (58.6 mL, 1,476 mmol) was added dropwise sodium persulfate (17.1 g, 71.7 mmol). The reaction mixture was stirred at 90 for 2 h and was further stirred at rt for 12 h. After dilution with water, the mixture was extracted with isopropanol/chloroform (1/3) and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (70% n-hexane/EtOAc) to afford 3,5-dichloropyrazin-2-carboxamide (5.06 g, 36%) as an oil.

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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ST Pharm Co. Ltd.; Kim, Kyeong Jin; Kim, Kwang Rok; Kim, Wook Il; Bang, Hyeong Tae; Yoon, Ji Hye; Im, Hwan Jeong; Ho, Cheong Nyeong; (50 pag.)KR2016/7347; (2016); A;,
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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 36070-80-1

To a solution of 5-chloropyrazine-2-carboxylic acid (300 mg, 1.89 mmol) in CH2C12 (3.8 mL) was added EDCI (401 mg, 2.09 mmol), DMAP (12.5 mg, 0.102 mmol) and MeOH (0.15 mL, 3.7 mmol) at room temperature. After stirring for 2 h, the reaction was quenched by adding saturated NH4C1 solution. The crude products were extracted with CH2C12 (x3), and the combined organic extracts were washed with brine, dried (MgS04), and concentrated in vacuo. The residue was purified by flash column chromatography (hexane/EtOAc = 9/1 to 7/1) to afford methyl 5-chloropyrazine-2-carboxylate (213 g, 65%) as a white solid. NMR (300 MHz, CDCh) delta 9.12 (d, J = 1.8 Hz, 1H), 8.73 (d, J = 1.8 Hz, 1H), 4.07 (s, 3H).

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; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, A new synthetic method of this compound is introduced below., name: 2-Amino-5-bromopyrazine

Step 1. A solution of 5-bromopyrazin-2-amine (4.53 g, 26.03 mmol), (4-isopropylsulfonylphenyl)boronic acid (7.125 g, 31.24 mmol) and K3PO4 (11.05 g, 52.06 mmol) in MeCN (90.60 mL)/Water (22.65 mL) was degassed with nitrogen. Pd[P(tBu)3]2. (665.4 mg, 1.302 mmol) was added and the degassing/flushing with nitrogen repeated. The reaction mixture was heated at 60 C. for 4 hours. A further 300 mg catalyst added over the next 30 min and the reaction mixture was stirred for 2 hours at 66 C. to give complete disappearance of the 5-bromopyrazine-2-amine starting material. The reaction mixture was cooled to ambient temperature and diluted with ethylacetate/water. The organic layer was separated and the aqueous layer extracted again with ethylacetate. The combined organic extracts were washed with aq NaCl/NaHCO3, dried over MgSO4, then filtered through a short silica gel column washing through with ethylacetate. The eluant was concentrated in vacuo to about 40 ml volume. The product was filtered off and the product washed with ethylacetate, petrol ether to give 5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine a pale yellow powder (5.65 g, 78%). %). 1H NMR (400.0 MHz, DMSO-d6) delta 8.70 (s, 1H), 8.2 (d, 2H), 8.02 (s, 1H), 7.90 (d, 2H), 6.9 (s, 2H), 5.76 (s, 1H), 3.4-3.5 (m, 1H), 1.20 (d, 6H); LC/MS m/z 278.0 [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; VERTEX PHARMACEUTICALS INCORPORATED; Charrier, Jean-Damien; Storck, Pierre-Henri; Pinder, Joanne; Studley, John R.; US2013/115312; (2013); 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 32974-92-8 as follows. category: Pyrazines

To a solution of 6 g (40 mmol) 1-(3-Ethyl-pyrazin-2-yl)-ethanone in 21 ml HBr (33%) and 7 ml methanol was added 2 ml (40 mmol) bromine and the mixture was heated to 60 C for 3 h. After removal of the volatiles under reduced pressure the residue was washed with diethyl ether and ethyl acetate. 6.4 g (41%) of the title compound was obtained as grey solid. MS (m/e): 229.1 (M+H, 100%).

According to the analysis of related databases, 32974-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. Hoffmann-La Roche AG; WO2004/14884; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Safety of (3-Chloropyrazin-2-yl)methanamine hydrochloride

trichloromethyl chloroformate (105 mmol, 12.68 mL) in tetrahydrofuran (100 mL) was cooled to 0 C and a solution of azetidine (88 mmol, 5 g) and N,N-diisopropylethylamine (193 mmol, 33.6 mL) in tetrahydrofuran (100 mL) was added slowly in 25 minutes. After stirring at 0 C for one hour the solids were removed by filtration and the filtrate was concentrated at 50 mbar (50C bath temperature). The residue was added to a solution of 2-aminomethyl-3-chloropyrazine hydrochloride (66.7 mmol, 12 g) and triethylamine (200 mmol, 27.9 mL) in dichloromethane (200 mL) and the reaction mixture was stirred for three hours. The solids were removed by filtration and the filtrate was concentrated in vacuo. Purification using column chromatography (silica gel; gradient dichloromethane / methanol 100:0 to 95:5) yielded 9.5 g of N-((3-chloropyrazin-2-yl)methyl)azetidine-1-carboxamide.

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSD Oss B.V.; Man, de, Adrianus, Petrus, Antonius; Sterrenburg, Jan-Gerard; Raaijmakers, Hans C.A.; Kaptein, Allard; Oubrie, Arthur A.; Rewinkel, Johannes, Bernardus, Maria; Jans, Christiaan, Gerardus, Johannes, Maria; Wijkmans, Jacobus C.H.M.; Barf, Tjeerd A.; Gao, Xiaolei; Boga, Sobhana Babu; Yao, Xin; Zhu, Hugh Y.; Cooper, Allen B.; Kim, Ronald M.; EP2548877; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5521-58-4, 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. 5521-58-4, name is 5-Methylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

3-[(Phenylmethyl)oxy]-5-(tetrahydro-2H-pyran-4-yloxy)benzoic acid (3.14 g, 9.5 mmol), 2-amino-5 methylpyrazine (2.08 g, 19.0 mmol) and EtaATU (4.70 g, 12.35 mmol) were dissolved in DMF (12.5 niL) and DIPEA (3.31 mL, 19.0 mmol) added. The resultant mixture was stirred at RT for 20 hours. The mixture was quenched with water (150 mL) and extracted with ethyl acetate (2 x 75 mL), washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica, eluting with 0-50% ethyl acetate in isohexane, to give the desired compound as a pale yellow gum (1.70 g). m/z 420 (M+Eta)+

The synthetic route of 5-Methylpyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem