Tag: M.W=100-200

Some common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, molecular formula is C9H16N2O2, 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. Computed Properties of C9H16N2O2

General procedure: n-Butyllithum (500 muL, 1.6 M in hexane) was added dropwise to a stirred solution of (2R)-2,5 -dihydro-2-isopropyl-3,6-dimethoxypyrazine( 150 jiL, 0.83 mmol) in 3 mL dry THF at -78°C under argon atmosphere. The resultant mixture was allowed to be stirred for additional 5 mm. The obtained yellow solution was subsequently transferred via a double-tipped needle to stirred slurry of copper (I) cyanide (38 mg, 0.42 mmol) in 2 mL THF at -78°C under argon. This mixture was stirred at 0 °C for around 1.5 mm to afford cyanocuprate as a tan colored solution. The reaction was then immediately cooled down to-78 °C. A solution of the iodide 6 (0.28 mmol) in 10 mL dry THF was then added dropwise. The reaction mixture was stirred at -78 °C for 30 mm and then for 16 h at -25 °C under argon. The reaction was quenched by adding a 1:9 mixture of aqueous ammonia/saturated aqueous ammonium chloride (15 mL). The aqueous phase was further extracted with diethyl ether (3 x20 mL). The organic layer was combined and then washed with the 1:9 mixtures of concentrated aqueous ammonia/saturated aqueous ammonium chloride, followed by brine, and then dried with anhydrous Na2SO4. After removing the volatile components with rotavapor, the crude product was purified by silica gel flash chromatography (hexane:EtOAc = 4:1 then 3:1) afforded the desired product 7 as colorless oil. [0066] 7b R = Et, 79percent yield. [CL]D179 +6.75(c 1.01, CHC13); 1H-NMR (600 MHz, DMSO-d6,64°C): delta 0.65(d, 3H,J= 6.8 Hz), 0.99(d, 3H,J= 6.8 Hz), 1.10(t, 3H,J= 7.0 Hz), 1.25(s,3H), 1.37(s, 3H), 1.45-1.48(m, 1H), 1.50-1.60(m, 3H), 1.71-1.75(m, 1H), 1.82-1.85(m, 1H),2.15-2.20(m, 1H), 3.14-3.19(m, 2H), 3.25(s, 3H), 3.60(s, 3H), 3.61(s, 3H), 3.89(t, 1H, J 3.6Hz), 3.98(dd, 1H, J= 10.8Hz, 4.0 Hz), 3.99-4.01(m, 2H), 4.53(d, 1H, J 5.9 Hz), 4.55(d, 1H,J= 5.9 Hz), 4.86(s, 1H), 5.09(s, 2H), 7.30-7.31(m, 1H), 7.33-7.36(m, 4H); 13C-NMR (150MHz, DMSO-d6 rotamers): delta 14.20, 15.17, 16.38, 19.01, 24.64, 26.23, 27.90, 30.73, 31.03,37.52, 37.88, 52.07, 53.83, 54.03, 54.27, 59.77, 65.81, 66.13, 83.29, 83.41, 83.66, 83.70,84.90, 109.05, 109.22, 111.32, 127.22, 127.60, 127.68, 128.21, 128.36, 136.97, 137.26,155.52, 162.76, 163.03, 163.11; MS(ESI) mlz: 590 [M+H] HRMS: calculated forC31H48N308 ([M+H]+) 590.3441, found 590.3440.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 109838-85-9, its application will become more common.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; ZHENG, Weihong; LUO, Minkui; IBANEZ SANCHEZ, Glorymar del Valle; WO2013/63417; (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 23688-89-3 as follows. name: 6-Chloropyrazine-2-carboxylic acid

The preparation method is:0.185 g (ie 1.0 mmol) of 2-phenoxyaniline, 0.158 g (ie 1.0 mmol) of 6-chloropyrazine-2-carboxylic acid and 30 ml of dichloromethane were added to the reaction flask. Then 0.202 g (ie 2.0 mmol) of Et3N was added, followed by 0.287 mg (1.5 mmol) of EDCl, 0.20 g (ie 1.5 mmol) of HOBt,After reacting at 25 C for 2.5 hours, the reaction was completed by TLC, and the reaction was completed. The reaction solution was washed twice with water and once with saturated brine. The organic phase is dried over anhydrous sodium sulfate and de-solued to give a crude product. Recrystallization of ethanol to give a brick red solid is 6-chloro-N-(2-phenoxyphenyl)pyrazine-2-carboxamide, m.p (melting point): 138-140 C, yield: 79.0%;

According to the analysis of related databases, 23688-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Kaiai Network Technology Co., Ltd.; Xu Liyong; (8 pag.)CN108892646; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 25911-65-3, A common heterocyclic compound, 25911-65-3, name is 3-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

c) 4-Amino-2-(methoxymethoxymethyl)pteridine Obtained using the procedure described in section c of Example 2, starting with 12.0 g (0.10 mole) of 3-amino-2-pyrazinecarbonitrile and 18.0 g (0.15 mole) of 2-(methoxymethoxy)acetamidine in 400 ml of absolute ethanol. Refluxing time: 4 hours. Yld: 15.8 g (71%), m.p. 129-131 C. (ethanol). NMR (DMSO-d6): delta=3.3 (3H, s); 4.5 (2H, s); 4.7 (2H, s); 8.2 (2H, peak exchangeable with CF3 COOD); 8.7 (1H, d); 8.9 (1H, d).

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; Lipha, Lyonnaise Industrielle Pharmaceutique; US5167949; (1992); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-79-8, name is 6-Chloropyrazine-2-carboxamide, 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 36070-79-8, name: 6-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).

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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

Electric Literature of 4774-14-5, These common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, 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.

Step 1. Preparation of (2-chlorophenyl)-(3,5-dichloropyrazin-2-yl)-methanol. To a -20 C. solution of n-butyllithium (2.5 M in hexane, Aldrich, 26.5 mmol) in dry tetrahydrofuran (200 mL) under argon was added 2,2,6,6-tetramethylpiperidine (Aldrich, 11.5 mL, 66.5 mmol, 1.22 eq). The resulting solution was warmed to 0 C. over 0.5 hour period. The solution was then cooled to -78 C., and a solution of 2,6-dichloropyrazine (Aldrich, 8.24 g, 55.3 mmol, 1.0 eq) in tetrahydrofuran was slowly added via a syringe. After addition was complete, the resulting mixture was stirred at -78 C. for an additional 1 hour after which 2-chlorobenzaldehyde (Aldrich, 9.3 mL, 83 mmole, 1.5 eq) was added drop wise via a syringe. The reaction mixture was stirred for an additional 1 hour, quenched with hydrochloric acid (18 mL, 220 mmol, 4 eq)/ethanol (75 mL)/tetrahydrofuran (90 mL) mixture, and then warmed to room temperature. The reaction mixture was diluted with aqueous saturated sodium bicarbonate solution and extracted with ether. The organic layer was separated and washed with brine, dried over sodium sulfate, filtered, and concentrated to give a crude oil which was purified via chromatography using dichloromethane/hexanes (1:1) as the eluent to give (2-chlorophenyl)-(3,5-dichloropyrazin-2-yl)methanol (12.8 g, 44 mmol, 80% yield). Mass spec M+1=290.

Statistics shows that 2,6-Dichloropyrazine is playing an increasingly important role. we look forward to future research findings about 4774-14-5.

Reference:
Patent; Arora, Nidhi; Billedeau, Roland Joseph; Dewdney, Nolan James; Gabriel, Tobias; Goldstein, David Michael; O’Yang, Counde; Soth, Michael; US2005/197340; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, 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 5521-55-1, HPLC of Formula: C6H6N2O2

General procedure: To the dipeptide salt (7 or 11, 1 mmol) in Schemes 2 and 3 wasadded a solution of 7 N NH3 in CH3OH (10 mL) and reaction mixturewas stirred for 10 min at 0 C. The solvent was evaporatedunder reduced pressure to afford free peptides, which was dissolvedin DMF (4 mL) and cooled to 4 C. To this reaction mixturerequisite carboxylic acid (1 mmol), DIC (1.1 mmol) and HOBt(1.1 mmol) was added and stirring continued at 4 C for 36 h. Thesolvent was removed under reduced pressure and the resultingresidue purified by column chromatography over neutral alumina using CHCl3/CH3OH (4:1) as eluant to afford desired peptides.The peptides were checked for their homogeneity on aShimadzu SPD-M20A HPLC system using a Supelcosil LC-8(25 cm 4.6 mm ID) column. The peptides were analyzed by usingan isocratic solvent system of CH3CN-H2O-TFA (70:30:0.8%) usinga SUPELCOSIL C-18 column with a flow rate of 1 mL/min

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Reference:
Article; Meena, Chhuttan L.; Thakur, Avinash; Nandekar, Prajwal P.; Sangamwar, Abhay T.; Sharma, Shyam S.; Jain, Rahul; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5641 – 5653;,
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. 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 38557-72-1

To 2-chloro-3,5-dimethylpyrazine (2.8 g) were added 1-(tert-butoxycarbonyl)piperazine (3.7 g),palladium(II)acetate (225 mg),2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (953 mg),sodium tert-butoxide (2.7 g) and toluene (40 mL) and the mixture was stirred under reflux for 8 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The solvent was evaporated and the obtained residue was purified by column chromatography (hexane:ethyl acetate)to give 3′,5′-dimethyl-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (5 g).

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; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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 mixture of 2-chloropyrazine (4.00 g) and hydrazine hydrate was heated at 110 C. for 1 h, and then cooled to room temperature. The mixture was filtered to give the title compound as a solid (2.30 g, 60.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 111.0 (M+1).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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 suspension of 5-aminopyrazine-2-carbonitrile (44.3 mg, 0.37 mmol) in THF (10 mL) was added NaH (24.4 mg, 0.61 mmol) at 0 C. The resulting mixture was stirred at ambient temperature for 1 h. A solution of compound 3 05-5 (120 mg, 0.3 lmmol) in THF (2 mL) was added and stirred at 55 C for 3.5 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography (hexanes/ethyl acetate: 3/1) to afford the title compound 306-5 as a yellow solid (110 mg, 77 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminopyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-25-1,Some common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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 methyl-5-chloropyrazine-2-carboxylate (120 mg, 0.70 mmol) in a mixture of acetonitrile (2 ml) and DMF (1 ml) was added lithium chloride (295 mg, 6.95 mmol). The suspension was heated to 1600C for 5 mins in a Smith creator microwave after which time the reaction was diluted with water (10 ml). Saturated sodium bicarbonate solution (20 ml) was added and the aqueous layered extracted twice with ethyl acetate (30 ml). The combined organics were discarded and the aqueous layer adjusted to pH 4 with IN hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate (20 ml) and the combined organics washed with water (2 x 20 mlL), brine (10 ml) and dried (MgSO4). The volatiles were removed to give the title compound as a colourless solid (68 mg), 1H NMR delta (CDCl3): 7.20 (IH, br s), 8.72 (IH, s), 9.21 – 9.21 (IH, m); m/z 157 (M-H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-chloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125958; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem