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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 33332-28-4

Pre Step A 6-(Methyloxy)-2-pyrazinamine A mixture of 6-chloro-2-pyrazinamine (200 mg, 1.544 mmol) and sodium methoxide (250 mg, 4.63 mmol) in methanol (3.9 ml) was heated to 130° C. via a microwave reactor for 60 min. The crude product mixture was purified by RP-HPLC to give 6-(methyloxy)-2-pyrazinamine (154 mg, 1.231 mmol, 80percent yield). MS (ES+) m/z 125.8 (MH+).

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; Glaxosmithkline LLC; Aubart, Kelly M.; Benowitz, Andrew B.; Fang, Yuhong; Hoffman, James; Karpinski, Joseph M.; Knox, Andrew Nicholson; Liao, Xiangmin; Qin, Donghui; Shi, Dongchuan; Spletstoser, Jared T.; US2013/345120; (2013); A1;; ; Patent; GlaxoSmithKline Intellectual Property (No. 2) Limited; Aubart, Kelly M.; Benowitz, Andrew B.; Fang, Yuhong; Hoffman, James; Karpinski, Joseph M.; Knox, Andrew Nicholson; Liao, Xiangmin; Qin, Donghui; Shi, Dongchuan; Spletstoser, Jared T.; US8901119; (2014); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 68774-77-6, 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. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1.28. (3 ?,4S)-4-methylbenzyl 4-(([l,2,4]triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3- fluoropiperidine-l-carboxylate (E2-1.2). [0265] A mixture of 8-chloro-[l,2,4]triazolo[4,3-a]pyrazine (120 mg, 0.78 mmol), (3R,4S)-4- methylbenzyl 4-(aminomethyl)-3-fluoropiperidine-l-carboxylate hydrochloride (297 mg, 0.94 mmol) and DIPEA (0.65 mL, 3.9 mmol) in n-BuOH (4 mL) was heated to 120C under N2 atmosphere. After stirring overnight at 120C, the mixture was cooled down to room temperature and concentrated under vacuum. The concentrate was partitioned into EtOAc 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 (eluent: 100% ethyl acetate) to afford the title compound as a brown powder (187 mg, 78%). MS (ESI) calcd for C20H23FN6O2: 398.2; found: 399.3[M+H]. *H NMR (400 MHz, CD3OD) delta 9.09 (s, 1H), 7.69 (d, J = 4.8 Hz, 1H), 7.30 (d, J = 4.8 Hz, 1H), 7.24 (d, J = 8.0 Hz, 2H), 7.16 (d, J = 8.0 Hz, 2H), 5.08 (s, 2H), 4.85-4.71 (m, 1H), 4.50-4.40 (m, 1H), 4.28-4.20 (m, 1H), 3.68-3.63 (m, 1H), 3.60-3.55 (m, 1H), 3.11-3.00 (m, 1H), 2.95-2.80 (m, 1H), 2.33 (s, 3H), 2.30-2.11 (m, 1H), 1.71-1.57 (m, 2H).

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, 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, other downstream synthetic routes, hurry up and to see.

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

Synthetic Route of 186534-02-1, 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. 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A cyclopentanone was added sequentially to a 25O mL three-necked flask(1 OmL, 0.115mo 1),Morpholine (1 OmL, 0.114 mol), benzene 100 mL,Reflux reaction to the oil-water separator after the formation of anhydrous,The reaction solution was cooled to room temperature,Add p-methoxybenzaldehyde(13 mL, 0.115 mol), refluxed for 8 h,TLC (petroleum ether – ethyl acetate = 1: 1) detection reaction is basically complete,Slowly add 6mol / L HC1 50mL,Stirring at room temperature lh,Then add 10% NaHC03 solution 115mL,Stirring at room temperature for 30min,The solution was poured into a separatory funnel,The layers were allowed to stand, the organic layer was dried over anhydrous sodium sulfate,concentrate. Dissolved in 40 mL of absolute ethanol,Add 1.5g of Chuanxiong aldehyde (0.0lmo 1),Ice bath conditions slowly add 10% NaOH ethanol solution 5mL,Reaction about lh,TLC (petroleum ether – ethyl acetate = 2: 1) detection reaction is basically complete,The precipitate was filtered off and the precipitate was washed with absolute ethanol,Purification by silica gel column chromatography (dichloromethane: ethyl acetate = 2: 1) gave 2.01 of Z1 yellow crystals,The yield was 6 1.2%.

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, 3,5,6-Trimethylpyrazine-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anhui University of Chinese Medicine; Hefei Medical Engineering Pharmaceutical Co., Ltd.; Hefei Enruite Pharmaceutical Co., Ltd.; Li Jiaming; He Guangwei; Zhang Yang; Huang Weijun; Zhang Yanchun; Liu Weizhong; Zuo Jian; Liu Huicai; Zhu Panhu; Wang Yujun; (14 pag.)CN106518791; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6863-73-6,Some common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, 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 1 3-Chloro-2-nitropyrazine STR11 Step A: S,S-Dimethyl-N-(3-chloropyrazin-2-yl)sulfilimine (2) To a mechanically stirred solution of 3.9 g (0.05 mol) dimethyl sulfoxide in 30 ml dry methylene chloride at -78 under nitrogen is added 13.1 g (0.046 mol) trifluoromethanesulfonic anhydride dropwise to afford a white precipitate. To this is added a solution of 5.0 g (0.039 mol) 2-amino-3-chloropyrazine (1) in 30 ml methylene chloride/15 ml dimethyl sulfoxide and the resulting solution is stirred at -78 for 2 hours and at -55 for 1 hour. The reaction mixture is then quenched with 50 ml of 5% aqueous sodium bicarbonate solution and stirred at -5 for 5 minutes. The reaction mixture is diluted with 200 ml methylene chloride and the phases are separated. The aqueous phase is extracted with 250 ml methylene chloride and the combined organic phases are washed with 3*75 ml portions of water and dried over anhydrous sodium sulfate. The solvent is removed from the rotary evaporator to give 5.8 g (79%) of 2 as yellow crystals, m.p. 106-108.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloropyrazin-2-amine, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US4709035; (1987); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 3149-28-8, 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 3149-28-8 as follows.

Alternate synthesis of (8) A solution of 5.4 ml of 2,2,6,6-tetramethylpiperidine, in 300 ml of dry THF was cooled to -8C as 19 ml of 1.6 M butyllithium (0.03 mol) in hexane was added dropwise. The reaction was stirred 20 min then cooled to -77C. A solution of 2.5 g of 2-methoxypyrazine (0.023 mol) in 5 ml of THF was added dropwise to the reaction. After 5h, 2.9 g of 3-quinuclidinone (0.023 mol) in 5 ml of THF was added dropwise and the reaction stirred another h. A solution of 8 ml of concentrated HCl and 4 ml of ethanol was added, the cooling was removed, and when the temperature reached -10C, 20 ml of 5 N NaOH was added. The volatile organics were evaporated and the residue extracted 3X with 50 ml of CHCl3 The extracts were washed with brine, dried, and the solvent evaporated to give a clear yellow liquid that solidified on further drying. Recrystallization from ether gave 3.53 g of (8) identical to the material produced in the previous reaction.

According to the analysis of related databases, 3149-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVO NORDISK A/S; EP521067; (1995); B1;,
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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C6H6N2O2

tert-Butyl (5-methylpyrazin-2-yl)carbamate To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added 5-methylpyrazine-2-carboxylic acid (1.0 eq), tert-butanol (3.5 vols) and di-isopropylethylamine (1.5 eq) under a nitrogen atmosphere. The mixture was heated to 82 C., then diphenylphosphorylazide (1.0 eq) was added over a time period of 5-14 hours, maintaining the temperature of the reaction mixture at approximately 82 C. The reaction mixture was stirred for at least 1.5 hours, and then cooled to approximately 60 C. A solution of 4% w/w sodium hydroxide (1.75 eq) was added over a period of 2 hours. The mixture was cooled to 15 C. over at least 5 hours then held at 15 C. for 3 hours. The batch was then filtered, and the solid slurry washed with water (2 vols). The batch was again slurry washed with water (2 vols). After drying at 55-60 C. overnight, the desired product was obtained as a solid (corrected yield 56-63%). 1H NMR delta (400 MHz CDCl3): 9.18 (s, 1H), 8.17 (bs, 1H), 8.11 (s, 1H), 2.51 (s, 3H), 1.56 (s, 9H)

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US2010/210621; (2010); 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. 21279-64-1, name is 5-Chloropyrazine-2-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Chloropyrazine-2-carboxamide

General procedure: 150 mg (0.952 mmol) of 5-Cl-PZA (1) or 6-Cl-PZA (2) was dissolved in ethanol together with triethylamine (1 eq., 96 mg, 0.952 mmol). Three equivalents of corresponding alkylamine were added to the reaction mixture and refluxed in ethanol generally for 6 hours. The completion of the reaction was checked by TLC chromatography (eluent: hexane/ethyl acetate, 1:2). The crude product was absorbed on silica by solvent evaporation and purified by flash chromatography (hexane/ethyl acetate gradient elution).

According to the analysis of related databases, 21279-64-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Servusova, Barbora; Paterova, Pavla; Mandikova, Jana; Kubicek, Vladimir; Kucera, Radim; Kunes, Jiri; Dolezal, Martin; Zitko, Jan; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 450 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 23688-89-3, 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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

2-Phenoxyaniline (0.185 g, 1.0 mmol), 6-chloropyrazine-2-carboxylic acid (0.158 g, 1.0 mmol) and 30 mL of dichloromethane were added to the reaction flask, and Et3N (0.202 g, 2.0 mmol) was added. Then, EDCI (0.287 mg, 1.5 mmol), HOBt (0.20 g, 1.5 mmol) was added, and the reaction was carried out at 25 C for 2.5 hours. The reaction was completed by TLC, and the reaction was completed. The reaction mixture was washed twice with water and once with saturated brine. The organic phase is dried over anhydrous sodium sulfate, de-solued to give a crude product, and recrystallized from ethanol.Brick red solid, m.p. 138-140 C, yield 79.0%

The chemical industry reduces the impact on the environment during synthesis 6-Chloropyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chen Lei; (6 pag.)CN108997228; (2018); 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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 56423-63-3

Example 88CPreparation of Compound (95c) A mixture of compound (95b) (1.70 g), K2CO3 (1.87 g, 4 equiv.), Pd(Ph3P)2Cl2 (72.0 mg, 3%), and 2-bromopyrazine (1.07 g, 2 equiv.) in dioxane (18 mL) and H2O (6 mL) was degassed within an ultrasonic cleaner for 1 hr under argon protection. The mixture was heated at reflux with stirring for 3 hr. The residue was partitioned with EtOAc (80 mL) and H2O (30 mL). The EtOAc layer was washed with brine, dried on MgSO4 and purified through FCC (EtOAc/Hexanes=1/1) to give 1.5 g of compound (95c).

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; BIOMARIN PHARMACEUTICAL INC.; US2011/178065; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-28-4, A common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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.

Synthesis 2-1 -B 5-bromo-6-chloropyrazin-2-amine 6-Chloropyrazin-2-amine (2.50 g, 19.3 mmol) was stirred in dichloromethane (60 mL) and cooled to O°C. N-Bromosuccinimide (2.92 g, 16.4 mmol) was added slowly and the reaction mixture was stirred at 0°C for 60 minutes. The reaction mixture was filtered through celite and concentrated to give a brown oil. Purification by flash chromatography, eluting with 0-25percent ethyl acetate-hexane, gave the title compound as a yellow solid (1.69 g, 8.16 mmol, 42percent). 1HMR (d6-DMSO, 400 MHz) delta 7.65 (s, 1H), 7.1 (br s, 2H). LC-MS (1) rt 1.46 min; m/z (ESI-) 205 (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; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem