Tag: M.W=100-200

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

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

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

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

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

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. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 68774-77-6

Step 1. (3S, 4 ?)-tert-butyl 4-(([l,2,4]triazolo[4,3-o]pyrazin-8-ylamino)methyl)-3- fluoropiperidine-l-carboxylate [0187] A mixture of 8-chloro-[l,2,4]triazolo[4,3-a]pyrazine (2.00 g, 12.94 mmol), (3S, 4 ?)-tert-butyl 4- (aminomethyl)-3-fluoropiperidine-l-carboxylate (2.86 g , 12.32 mmol) and DIPEA (4.07 mL, 24.64 mmol) in n-butyl alcohol (40 mL) was heated to 120 C in the sealed tube under N2 atmosphere. After stirring overnight, the mixture was cooled to rt and concentrated under reduce pressure. The concentrate was partitioned into DCM and water. The organic phase was washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (MeOH/DCM = 1/20) to afford the title compound as a pale-yellow powder (2.91g, 67%). MS (ESI) calcd for C16H23FN602: 350.2; found: 351.7[M+H]. *H NM (400 MHz, CD3OD) delta 9.09 (s, 1H), 7.70 (d, J = 4.8 Hz, 1H), 7.31 (d, J = 4.8 Hz, 1H), 4.86-4.73 (m, 1H), 4.42-4.35 (m, 1H), 4.19-4.16 (m, 1H), 3.67-3.62 (m , 1H), 3.59-3.54 (m, 1H), 3.05-2.74 (m, 2H), 2.25 -2.10 (m, 1H), 1.67-1.53 (m, 2H), 1.46 (s, 9H).

According to the analysis of related databases, 68774-77-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (239 pag.)WO2016/100349; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4, Safety of 2,5-Dichloropyrazine

Step C: (S)-3 -(6-(Methylsulfonyl)pyridin-3 -ylamino)- 1 -(piperidin-4- yl)pyrrolidin-2-one (0.076 g, 0.22 mmol) and 2,5-dichloropyrazine (0.054 g, 0.36 mmol) were dissolved in NMP (0.45 mL) and treated with DIEA (0.098 mL, 0.56 mmol). The mixture was stirred at 80 °C overnight and then cooled to ambient temperature. The reaction mixture was partitioned between EtOAc (40 mL) and FLO (20 mL). The mixture was filtered through a 0.45 muiotaeta nylon membrane and the solids were washed with EtOAc and then dried under high vacuum to provide (S)-l-(l-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(6- (methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one (0.030 g, 0.067 mmol, 30percent).

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; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-28-4,Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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 8 N-(6-Chloro-pyrazin-2-yl)-2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 8.5 g (30 mmols) of methyl 2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 3.9 g (30 mmols) of 2-amino-6-chloro-pyrazine were reacted in 600 ml of xylene and worked up analogous to Example 1, yielding 7.3 g (64percent of theory) of N-(6-chloro-pyrazin-2-yl)-2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide. Melting point: 233°-235° C. (from xylene). C15 H13 ClN4 O4 S (380.83): Calc.: C–47.31percent; H–3.44percent; Cl–9.31percent; N–14.71percent; S–8.42percent. Found: C–47.42percent; H–3.44percent; Cl–9.50percent; N–14.62percent; S–8.51percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-chloropyrazine, its application will become more common.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
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. 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-(3-Ethylpyrazin-2-yl)ethanone

General procedure: The ligands L1-L4 were synthesized by reflux method. Shown in Scheme 1, 5mM of 2-Acetyl-3-ethylpyrazine and thiosemicarbazides (L1), 5mM of 2-Acetyl-3-ethylpyrazine and 4-methylthiosemicarbazide (L2), 5mM of 2-Acetyl-3-ethylpyrazine and 4-phenylthiosemicarbazide (L3), and 5mM of 2-Acetyl-3-ethylpyrazine and 3-pyrrolethiosemicarbazide (L4) were stirred in CH3OH for 3 h at 65C. The ligands were precipitated and filtered. L1-L4 were characterized by infrared spectroscopy, electrospray ionization mass spectrometry (ESI-MS), 1H NMR, and 13C NMR (Supplementary Figs S4- S31).

The synthetic route of 32974-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khan, Muhammad Hamid; Cai, Meiling; Li, Shanhe; Zhang, Zhenlei; Zhang, Juzheng; Wen, Xiaoan; Sun, Hongbin; Liang, Hong; Yang, Feng; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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 59489-32-6 as follows. Computed Properties of C6H7ClN2

Pd2(dba)3-CHC13 (5 mg, 0.5 mol %), ligand 1 (8 mg, 2 mol %) and 1.4 eq sodium tert- butoxide (13 mg, 0.14 mmol) were weighed in air and transferred into a microwave tube, followed by dioxane (750 muL), 1.0 eq JVrlambda/-dimethyl-l-(piperidin-4-yl)-2’/f-spiro[piperidine-4,41- quinolineJ-rp’i^O-carboxamide (36 mg, 0.10 rnmol) and 1.0 eq 5-chloro-2,3-dimethylpyrazine (14 mg). The tube was flushed with nitrogen, capped and stirred at 800C for 3 hours. The reaction was cooled to room temperature, diluted with methanol (500 muL), filtered (Whatman 0.45 mum PTFE) and subjected to reverse-phase HPLC purification (2-40% CH3CN gradient [w/ 0.1 % TFA (aq)] over / = 10 minutes, 750 muL injected, 35 mL/min) to yield compound no. 20. LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 463.4, retention time 2.13 minutes.

According to the analysis of related databases, 59489-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/100670; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem