Tag: M.W=100-200

63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C4H5ClN4

STEP2 Preparation of N’-(3-chloropyrazin-2-yl)-2,2,2-trifluoroacetohydrazide To a solution of 2-chloro-3-hydrazinylpyrazine (4.50 g, 31.1 mmol) in THF (104 mL) was dropwise added TFAA (5.72 mL, 40.5 mmol) at 0 C. The reaction mixture was stirred at room temperature for 1 hour and MeOH:DCMuenched with water. The mixture was extracted DCM, washed with water, dried over Na2SO4, filtered and concentrated in vacuo to afford N’-(3-chloropyrazin-2-yl)-2,2,2-trifluoroacetohydrazide (2.76 g, 37%) as a yellow solid, which was used for the next reaction without further purification. 1H-NMR (DMSO-d6, 400 MHz): delta 11.6 (1H, s), 9.47 (1H, s), 8.18 (1H, d, J=2.8 Hz), 7.88 (1H, d, J=2.4 Hz).

The synthetic route of 63286-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANDOK INC.; Lee, Jin-Hwa; Kim, Seung-Yong; Kim, Do-Ran; Ahn, Koo-Hyeon; Lee, Gwi-Bin; Kim, Doo-Seop; Hwang, Hyun-Sook; (74 pag.)US2017/204101; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 21279-62-9, name is 3-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 21279-62-9, name: 3-Chloropyrazine-2-carboxamide

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).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloropyrazine-2-carboxamide, and friends who are interested can also refer to it.

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

Application of 4774-14-5, 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. 4774-14-5, name is 2,6-Dichloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 2,6-dichloropyrazine (12.5 g, 83.91 mmol), 4-methylbenzenesulfonic acid hydrate (32 g, 168.2 mmol), NaI (120 g, 800.6 mmol) and 1,4,7,10,13- pentaoxacyclopentadecane (10 mL, 50.35 mmol) was added thiolane 1 ,1 -dioxide (200 mL) and the mixture heated to 150 0C and stirred for 3 hrs. The mixture was allowed to cool and added water 150 ml and neutralized with solid NaHCtheta3 It was then extracted into ether (3x300ml), washed with Sat. NaHCO3, brine then dried (MgSO4) and concentrated to give an orange solid. The product was washed with water and dried under high vacuum to give 2,6-diiodopyrazine as an orange solid (8.6 g, 31%). ES+ 332. IHNMR (CDCl3) 8.73 (2H, s).

The synthetic route of 2,6-Dichloropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; JIMENEZ, Juan-Miguel; STUDLEY, John; WO2010/11772; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 16298-03-6, 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 16298-03-6 as follows.

Bromine (3.91 g, 24.46 mmol) was added dropwise to a stirred mixture of 3- aminopyrazine-2-carboxylic acid methyl ester (1.27 g, 8.29 mmol) and hydrobromic acid (4.70 mL, 41.5 mmol) at 00C. A solution of sodium nitrite (1.44 g, 20.9 mmol) in water (6 mL) was then added dropwise. The reaction mixture was stirred for 15 min, brought to pH 8 with NaHCO3 (saturated, aqueous), and extracted with ethyl acetate (80 mL) and chloroform (50 mL). The combined organics were dried over MgSO4 and concentrated in vacuoto give 1.13 g (63%) of an orange oil which solidified on standing.

According to the analysis of related databases, 16298-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/121588; (2006); A2;; ; Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/121860; (2006); A2;; ; Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/121904; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6705-33-5, 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 6705-33-5 as follows.

To a mixture of 5-[4-(trifluoromethoxy)phenyl]-3H-l,3-benzoxazol-2-one (100 mg, 0.34 mmol), pyrazin-2-ylmethanol (111.9 mg, 1.02 mmol) and PPh3 (177.7 mg, 0.68 mmol) in THF (6 mL) was added the DIAD (136.99 mg, 0.68 mmol) at 0 C and the mixture was stirred under N2 at 20 C for 16 hours to give the mixture. The mixture was concentrated to dryness, diluted with H20 (10 mL), and extracted with EtOAc (10 mL chi 2). The combined organic phase was washed with brine (10 mL), dried over Na2SC>4, filtered and the filtrate was concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 35% to 45% to 60%) to give the product (100.9 mg, 260.4 muiotaetaomicron, 77% yield) as an oil. *H NMR DMSO-< 400MHz deltaH = 8.83 (s, 1H), 8.60 - 8.53 (m, 2H), 7.74 (d, 2H), 7.63 (s, 1H), 7.50 - 7.42 (m, 4H), 5.35 (s, 2H). LCMS Rt = 1.52 min in 2 min chromatography, MS ESI calcd. for C19H13F3N3O3 [M+H]+ 388.1, found 388.1. According to the analysis of related databases, 6705-33-5, the application of this compound in the production field has become more and more popular. Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33332-29-5, name is 2-Amino-5-chloropyrazine, 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 33332-29-5, name: 2-Amino-5-chloropyrazine

(c) 2-Amino-5-chloropyrazine (1.7 g) was dissolved in chloroform (190 ml) and pyridine (1.3 ml) was added under an argon atomosphere. The flask and its contents were protected from light and a solution of bromine (0.7 ml) in chloroform (85 ml) was added over a period of 1 hour. After stirring for 2 hours more bromine (0.07 ml) in chloroform (8.5 ml) was added. After stirring for 30 minutes, pyridine (0.2 ml) was added. The reaction mixture was stirred for a further 30 minutes then washed with water (50 ml) and the organic phase was separated. Volatile material was removed by evaporation and and the residue was purified by chromatography through a bed of silica (90 g), eluding with hexane (200 ml), followed by dichloromethane. Dichloromethane fractions containing the product were evaporated to give 2-amino-3-bromo-5-chloropyrazine (1.68 g); 1 H NMR (d6 -DMSO): 6.94 (br s, 2 H), 8.09 (s, 1 H); mass spectrum (+vc CI): 208 (M+H)+.

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-Amino-5-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zeneca Limited; US5866568; (1999); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 36070-80-1, A common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

At 0 C., a solution of compound (4-2) (0.89 g. 5 mmol) in dichloromethane (20 mL) is added into a solution of 3-methoxy aniline (0.62 g, 5 mmol) and triethylamine (1.01 g, 10 mmol) in dichloromethane (100 mL) over 30 minutes, and the reaction mixture is heated to room temperature overnight. The reaction mixture is diluted with dichloromethane (100 mL), and the organic phase is washed with water and brine, dried through anhydrous sodium sulfate and filtered. After being evaporated, the residue is purified by silica gel column chromatography to give compound (4-3) (1.1 g, 80%),

The synthetic route of 36070-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANGZHOU BENSHENG PHARACEUTICALS CO., LTD.; Xu, Rongzhen; Xie, Fuwen; Lai, Hongxi; Rong, Frank; US2013/178470; (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 54608-52-5 as follows. HPLC of Formula: C4H6N4

General procedure: Sodium (0.70 g, 30.44 mmol) was dissolved in 50 mL of anhydrous ethanol, and 2-chloro-6-hydrazinylpyrazine (2a) (4.00 g, 27.67 mmol) was added. The reaction solution was heated to 60 C until the mixture was totally dissolved. Keep the temperature of the reaction below 40 C, and diethyl maleate (4.77 g, 27.67 mmol) was added dropwise. The reaction was heated to 45 C and cooled to room temperature after 5 h. The reaction was quenched with glacial acetic acid (1.83 g, 30.44 mol) and stirred for 1 h. The resulting solution was evaporated in vacuo, dissolved in 50 mL of water, extracted with CH2Cl2 (3¡Á50 mL). The extracts was washed with brine, dried with anhydrous MgSO4 and evaporated to give the crude product, which was further purified with recrystallization (diehyl ether) as a yellow solid, 4.25 g.

According to the analysis of related databases, 54608-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Weijie; Li, Jiao; He, Kai; Huang, Fangfang; Ma, Yi; Li, Yuxin; Li, Qingshan; Xu, Fengbo; Chinese Chemical Letters; (2019); p. 417 – 420;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4774-14-5, name is 2,6-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 4774-14-5, name: 2,6-Dichloropyrazine

Step 1 [0666] To a solution of fert-butyl azetidin-3-ylcarbamate hydrochloride (LXIII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXIV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous NaaSO/t, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1 : 1) to yield fert-butyl (l-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17CIN4O2 mlz 285.1 (M+H).

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; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23980; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 36070-80-1,Some common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

5-Chloropyrazine-2-carboxylic acid (27, 7.84 g), N,N-dimethylformamide(120 mL), ethyl piperidine-4-carboxylate (16.0 mL),and N,N-diisopropylethylamine (25.0 mL) were mixed, followed bystirring at 90 C for 8 h. The reaction mixture was cooled to roomtemperature and ethyl acetate was added. The mixture was washedwith a dilute hydrochloric acid solution and dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration andthe filtrate was concentrated under reduced pressure. The obtainedsolid was washed with diisopropyl ether and dried to obtain 28 (6.80 g,49%) as a milky white solid: 1H NMR (CDCl3) delta 1.27 (3H, t,J = 7.0 Hz), 1.74-1.86 (2H, m), 2.02-2.11 (2H, m), 2.66 (1H, tt,J = 10.5, 4.1 Hz), 3.20-3.30 (2H, m), 4.17 (2H, q, J = 7.1 Hz),4.33-4.42 (2H, m), 8.02 (1H, d, J = 1.3 Hz), 8.86 (1H, d, J = 1.3 Hz);ESI-MS m/z 280 [(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 5-Chloropyrazine-2-carboxylic acid, its application will become more common.

Reference:
Article; Inagaki, Yusuke; Ino, Katsutoshi; Ishizu, Kenichiro; Koike, Takanori; Maeda, Jun; Negoro, Kenji; Shimoshige, Yukinori; Takahashi, Taisuke; Tanaka, Hiroaki; Tsukamoto, Issei; Yokoyama, Kazuhiro; Bioorganic and medicinal chemistry; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem