Tag: M.W=100-200

Related Products of 768-05-8, These common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, 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.

pyrazine-2-carbonvl azide.; pyrazine-2-carbohydrazide (11.1 g, 80 mmol) was dissolved in 140 mL of water and charged with 6N HC1 (13.3 mL, 80 mmol) and cooled to 0C. To the stirred reaction mixture was added a solution of sodium nitrite (8.3 g, 120 mmol) in 80 mL of water was added slowly over a period of 15-30 minutes using an addition funnel. After the addition was complete the reaction was warmed to room temperature and stirred for an additional 5h. The solution was the neutralized by the careful addition of solid NaHC03 and then extracted with CHC13 (3x). The pooled organic fractions were dried over Na2SO4, filtered, concentrated and dried under high vacuum overnight to yield 2.5 g (21%) the title acyl azide. The product was used in subsequent steps without purification. IH NMR (d6-DMSO 8 9.30, d, 1H; 8 9.03, d, 1H; 8 8.90, dd, 1H).

Statistics shows that Pyrazinoic acid hydrazide is playing an increasingly important role. we look forward to future research findings about 768-05-8.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/66163; (2005); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 912773-24-1, These common heterocyclic compound, 912773-24-1, name is 6-Bromoimidazo[1,2-a]pyrazine, 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 : To a solution of 6-bromoimidazo[l,2-a]pyrimidine (2.4 g, 12.1 mmol) in DMF, were sequentially added (4-methylpiperazin-r-yl)(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)methanone (80% of 4.1 g, 12.1 mmol), a solution of NaHC03 (3.1g, 36.3 mmol) in water (30 mL), water (3 mL) and (A-Phos)2PdCl2 (400 mg, 0.60 mmol). The reaction mixture was heated at 90 C for 4 h, then was diluted with water (100 mL) and extracted with EtOAc (3><100 mL). The combined organic layer was dried over Na2S04, filtered and concentrated under reduced pressure.. The residue was purified by flash column chromatography (silica gel, eluent CHCl3/MeOH 95 :5 to 85 : 15) to afford of (4-(imidazo[ 1 ,2-a]pyrazin-6-yl)phenyl)(4- methylpiperazin-l-yl)methanone (1.5 g, 65%). 1H NMR (400 MHz, CDC13) delta 8.60 (d, J~ 2,0 Hz, 1 H), 8.10 (d, J= 4.0, 1 H), 7.80 (d, J= 8.0 Hz, 1 H), 7.58 (m, 4 H) 7.39 (d, J= 8.0, 1 H), 3.84 (br s, 2 H), 3.50 (br s, 2 H), 2.40 (br s, 4 H), 2.35 (s, 3 H); MS (ESI) m/z 322 [M+1] Statistics shows that 6-Bromoimidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 912773-24-1. Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (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 4858-85-9 as follows. Formula: C4H2Cl2N2

A mixture 2,3-dichloropyrazine (50 g, 0.34 mmol) and concentrated aqueous ammonium hydroxide (200 mL) was stirred at 85 C. in a closed pressure vessel for 4 days. The mixture was cooled to 25 C., water (200 mL) was added, and the mixture was filtered. The solid was washed with water (400 mL), then with dichloromethane (400 mL) and dried under vacuum. Compound 100 was isolated as a white solid 32.5 g (73%). 1H NMR (400 MHz, DMSO-d6 delta 7.93 (d, 1H), 7.55 (d, 1H), 6.79 (bs, 2H).

According to the analysis of related databases, 4858-85-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2007/105864; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 875781-43-4,Some common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4BrN3, 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.

[0358] Step 1. To a suspension of 15A (1.0 equiv.) in THF (0.15 M) is added a solution of 2.0 M aqueous NaOH (3 equiv.). The homogeneous reaction mixture is stirred overnight, and then the organics are removed under reduced pressure. The aqueous residue is brought to pH–4 with 1.0 M aqueous HC1. The resulting precipitate is collected by filtration and rinsed with H20 to afford a solid of 1 5B. The filtrate is extracted with EtOAc (2x), and the organics are concentrated under reduced pressure to provide an additional portion of 15B.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, its application will become more common.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; WO2015/112806; (2015); A3;,
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. 6294-70-8, name is 5,6-Dimethylpyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6294-70-8

To an acetonitrile solution (8.00 mL) of the compound (519 mg) obtained in Reference Example 433 was added N-bromosuccinimide (749 mg) at 0C, and the reaction mixture was stirred at room temperature for 30 min. Aqueous sodium thiosulfate solution was added and the mixture was extracted twice with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated, and the obtained residue was purified by silica gel column chromatography (solvent; hexane/ethyl acetate=100/0 – 60/40) to give the title compound (619 mg). MS(ESI)m/z; 202,204[M+H]+

According to the analysis of related databases, 6294-70-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; OKUYAMA, Masahiro; FUKUNAGA, Kenji; USUI, Kenji; HAYASHI, Norimitsu; IIJIMA, Daisuke; HORIUCHI, Hideki; FUJIMOTO, Nobuaki; (218 pag.)EP3372601; (2018); 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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H16N2O2

The chiral auxiliary group (2.12 g, 11.5 mmol) was dissolved in dry THF solution (10 mL) and cooled to -78 o.n-Butyllithium reagent (2.5 M in hexane, 5.5 mL,13.8 mmol) was added dropwise to the reaction system and reacted at -78 °C for 30 minutes.Add the substrate (3.24 g, 12.1 mmol) in dry THF (10 mL).-78 oC reaction for 60 minutes. After the reaction system is quenched with saturated brine,Take it out from the -78 oC environment and naturally rise to room temperature.It was then extracted 3 times with ethyl acetate (30 mL x 3). Combine the organic phase,Backwash twice with saturated brine (50 mL x 2), dry over anhydrous magnesium sulfate.Filter and concentrate. Obtaining crude product by column chromatography for separation and purification(ethyl acetate: n-hexane = 1: 6), the product was obtained as a pale yellow solid.The yield is 3.85 g,Yield 70percent,

According to the analysis of related databases, 109838-85-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wang Lu; (17 pag.)CN109384806; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 710322-57-9,Some common heterocyclic compound, 710322-57-9, name is Methyl 5-formylpyrazine-2-carboxylate, molecular formula is C7H6N2O3, 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 5-formyl-pyrazine-2-carboxylic acid methyl ester (0.400 g, 2.40 mmol), piperidine (0.204 g, 2.40 mmol), and NaB(OAc)3H (1.40 g, 3.60 mmol) in DCM (10 mL) was stirred for 18 h at rt. The reaction was quenched by the addition of 10% aq. NaOH (10 mL) and the mixture was stirred for 30 min. The mixture was extracted with DCM (3*20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to yield the title compound (0.130 g, 23%).

The synthetic route of 710322-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Carruthers, Nicholas I.; Shah, Chandravadan R.; Swanson, Devin M.; US2005/222151; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 21279-62-9, 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 21279-62-9 as follows.

General procedure: Compounds 1-6 were prepared according to conventional organic synthesis methods. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was dissolved in THF (20 mL) in a round bottom flask and after that treated with two equivalents of the corresponding benzylamine and an equimolar amount of triethylamine. The reaction was conducted with continuous stirring and heating (70 C) under reflux in an oil bath for 15 h. Compounds 7-15 were synthesised using a microwave reactor with a focused field. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was put into a thick-walled tube together with the corresponding benzylamine (2.54 mmol), pyridine (1.27 mmol), methanol (approx. 5 mL) and a magnetic stir bar and then sealed with a special cap. The reaction parameters were set according to the previously published paper as follows-140 C, 30 min, 200 W [29]. Reaction progress was checked by TLC (hexane:ethyl acetate-1:1). Regardless of the synthesis method used,all reaction mixtures were adsorbed on silica and subjected to preparative flash chromatography (hexane and ethyl acetate, gradient elution, detection wavelengths 260 nm and 280 nm). Products were recrystallized from ethanol or ethanol and water if necessary. All final substances were chemically characterized (1H-NMR, 13C-NMR, IR, melting point and elemental analysis).

According to the analysis of related databases, 21279-62-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jandourek, Ondrej; Tauchman, Marek; Paterova, Pavla; Konecna, Klara; Navratilova, Lucie; Kubicek, Vladimir; Holas, Ondrej; Zitko, Jan; Dolezal, Martin; Molecules; vol. 22; 2; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 13535-07-4, 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 13535-07-4 as follows.

To a solution of (4S)-7-(6-methylpyridin-3-yl)-2,3,4,5-tetrahydro-l,4-methanopyrido[2,3- b][l,4]diazepine (600 mg, 2.378 mmol), triphosgene (706 mg, 2.378 mmol) and triethylamine (1.989 mL, 14.27 mmol) in tetrahydrofuran (THF) (15 mL) stirred under nitrogen at room temperature for 30 min was added 5-ethylpyrazin-2-amine (879 mg, 7.13 mmol). The reaction mixture was stirred at 70 C for 16 h and cooled to room temperature and then the reaction mixture was poured in to water and extracted with EtOAc (3 X 15 mL). The combined organic layers were washed with water, brine solution, dried over sodium sulfate and evaporated to give crude compound (TLC eluent: 5% MeOH in DCM: RrO. l; UV active). The crude compound was purified by column chromatography using Neutral Alumina and eluted with 30%EtO Ac/Pet ether to afford pure (4S)-N-(5- ethylpyrazin-2-yl)-7-(6-methylpyridin-3-yl)-3,4-dihydro-l,4-methanopyrido[2,3- b][l,4]diazepine-5(2H)-carboxamide (383 mg, 0.953 mmol, 40.1 % yield), LCMS (m/z): 402.3 [M+H]+.1H NMR (400 MHz, CDC13): delta ppm 13.65 (s, 1 H) 9.41 (d, J=1.53 Hz, 1 H) 9.11 (d, J=2.19 Hz, 1 H) 8.41 (dd, J=8.22, 2.52 Hz, 1 H) 8.22 (d, J=1.32 Hz, 1 H) 7.61 (d, J=7.89 Hz, 1 H) 7.40 (d, J=8.11 Hz, 1 H) 7.32 (d, J=8.11 Hz, 1 H) 5.70 (dd, J=6.03, 3.18 Hz, 1 H) 3.34 – 3.13 (m, 3 H) 3.02 (dd, J=12.06, 3.29 Hz, 1 H) 2.83 (q, J=7.53 Hz, 2 H) 2.64 (s, 3H) 2.40-2.34 (m, 1 H) 2.15 – 2.03 (m, 1 H) 1.33 (t, J=7.56 Hz, 3 H).

According to the analysis of related databases, 13535-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 23787-80-6, 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. 23787-80-6, name is 1-(3-Methylpyrazin-2-yl)ethanone belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Almac CRED (200 mg),NADP or NAD (10 mg), GDH (20 mg) and glucose (1.5 equiv) weremeasured into a 100 mL round bottomed flask then dissolved in0.1 M potassium phosphate buffer (pH 7, ca. 50 mL) and stirredat 30 C. Next, a solution of ketone (900-1700 mg) in DMSO(2.5-5 mL, depending on solubility) was added to the reactionand this was allowed to stir overnight under pH-stat control (pH7.0, adjusted with 1 M NaOH solution). The following day, reactionprogress was checked by 1H NMR. If not complete, additional CRED(100-200 mg), NADP or NAD (10 mg) and GDH (10 mg) wereadded and stirring was continued. This was repeated until the reactionreached completion or had stalled and would not go any further.

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, 1-(3-Methylpyrazin-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Rowan, Andrew S.; Moody, Thomas S.; Howard, Roger M.; Underwood, Toby J.; Miskelly, Iain R.; He, Yanan; Wang, Bo; Tetrahedron Asymmetry; vol. 24; 21-22; (2013); p. 1369 – 1381;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem