Tag: M.W=100-200

Some common heterocyclic compound, 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, molecular formula is C6H4ClN3, 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. HPLC of Formula: C6H4ClN3

To a solution of the product form step 2 (82.9 mg, 0.29 mmoi) in DMF (5 mL) was added NaH (14.0 mg 0.35 mrnol, 60 wt% in oil) at RT. The mixture was stirred at RT for 30 minutes, then 8.-chloroirnidazo[I2.-a]pyrazine (45.9 mg, 0.30 mmol) was added. The resulting mixture was heated to 40C for 2.5 hr. After cooling to RT, the mixture was poured into water (5 mL) and extracted with EtOAc (5 mL x 3). The combined organic layer was washed with brine, driedover MgSO4, filtered and concentrated in vacuo. The residue was purified by Prep-HPLC to afford the title compound (60 mg) as a brown solid. LRMS mz (M+H) 404,1 found, 404.1 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 69214-33-1, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); 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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2,3-Dichloropyrazine

A thick-walled reaction vessel (250 mL) charged with 2, 3-dichloropyrazine (14.9 g, 95 mmol) and 28-30% ammonium hydroxide (75 mL) was sealed in vacuo, submitted to a freeze-pump- thaw cycle and then heated with stirring to 135 C for 15 h. Upon cooling of the reaction mixture, needles were observed to form from the reaction mixture. The supernatant was decanted off and the residual solid was solubilized in hot methanol. The methanol solution was concentrated in vacuo and the resultant crude material (10. 8 g) was recrystallized from methanol (150 mL) to yield 8.26 g of the title compound (67% yield). mp 167-168 C ; Rf 0.5 (EtOAc-hexanes, 1 : 1, v/v, +0.5% v/v iPrNH2) ;’H NMR (DMSO-d6) 8 8.9 (s, 1H), 8. 7 (s, 1H), 5.0 (br s, 2H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4858-85-9.

Reference:
Patent; CARDIOME PHARMA CORPORATION; WO2005/34837; (2005); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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. Product Details of 75907-74-3

Compound 1a (6.08 g, 40 mmol) was dissolved in CHCl3 (60 mL),MnO2 (24 g, 280 mmol) was added, and the mixture was refluxed for 6 h, cooled, filtered, and concentrated. The crude productwas purified by column chromatography and eluted with ethyl acetate-petroleum ether (1:6) to yield 1b as bright yellowcrystals (4.2 g, 70%), mp 86C. ESI-MS m/z 151 [M + 1]+, C8H10N2O. 1H NMR (500 MHz, CDCl3, , ppm): 10.10 (1H, s,CHO), 2.75 (3H, s, CH3), 2.56 (6H, s, CH3 2). 13C NMR (125 MHz, CDCl3, , ppm): 21.39, 22.18, 141.91, 149.98, 151.54,155.45, 194.33.

The synthetic route of (3,5,6-Trimethylpyrazin-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Chen, Lang-Di; Liang, Xin-Tong; Liu, Wei-Xiong; Wu, Wen-Hao; Chemistry of Natural Compounds; vol. 53; 1; (2017); p. 114 – 117; Khim. Prir. Soedin.; vol. 53; 1; (2017); p. 96 – 98,3;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5521-56-2, name is 6-Methylpyrazin-2-amine, 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 5521-56-2, name: 6-Methylpyrazin-2-amine

Compound 10: 5-Bromo-6-methyl-pyrazin-2-ylamine. Under inert condition, to a solution 6-amino-2-methylpyrazine (100 mg, 1.0 equiv.) in a mixture of DMSO (4.6 mL) and water (0.2 mL) cooled by an ice bath, NBS (179 mg, 1.1 equiv.) was added in 3 portions. The light yellow mixture was stirred for 15 minutes, and then for 5 hrs at room temperature. The reaction mixture was hydrolysed with NaHCO3 saturated solution (25 mL) and extracted with EtOAc (30 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated. Purification by flash-chromatography afforded compound 10 as a light yellow solid in 36% yield. 1H-NMR (400 MHz, DMSO): 2.34 (bs, 3H, C-CH3); 6.52 (bs, 2H, NH2); 7.49 (s, 1H, Ar). M/Z (M[79Br]+H)+ = 188.2.

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, 6-Methylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Domain Therapeutics; Mayer, Stanislas; Schann, Stephan; EP2666775; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, 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. HPLC of Formula: C5H3ClN2O2

Example 41 6-chloro-N-(2-methoxy-1-(4 (trifluoromethoxy)phenyl)ethyl)pyrazine-2-carboxamide A mixture of 6-chloropyrazine-2-carboxylic acid (150 mg), thionyl chloride (0.345 mL), N,N-dimethylformamide (0.05 mL) and toluene (5 mL) was stirred at 100C for 1 hr. The mixture was concentrated under reduced pressure, to the residue were added tetrahydrofuran (5 mL), triethylamine (0.659 mL) and 2-methoxy-1-(4-(trifluoromethoxy)phenyl)ethanamine hydrochloride (257 mg), and the mixture was stirred at room temperature for 5 hr. The mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (225 mg). 1H NMR (300 MHz, CDCl3) delta 3.43 (3H, s), 3.77 (2H, d, J = 4.9 Hz), 5.23-5.46 (1H, m), 7.13-7.25 (2H, m), 7.39-7.53 (2H, m), 8.27 (1H, d, J = 7.5 Hz), 8.77 (1H, s), 9.27 (1H, s).

The synthetic route of 23688-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SETO, Masaki; BANNO, Yoshihiro; IMAEDA, Toshihiro; KAJITA, Yuichi; ASHIZAWA, Tomoko; KAWASAKI, Masanori; NAKAMURA, Shinji; MIKAMI, Satoshi; NOMURA, Izumi; TANIGUCHI, Takahiko; MARUI, Shogo; (153 pag.)EP3061754; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 25911-65-3,Some common heterocyclic compound, 25911-65-3, name is 3-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.

d) 4-Amino-2-[(2,2,2-trifluoroethoxy)methyl]pteridine Obtained using the procedure described in section c of Example 2, starting with 7.2 g (0.060 mole) of 3-amino-2-pyrazinecarbonitrile and 14.2 g (0.091 mole) of 2-(2,2,2-trifluoroethoxy)acetamidine in 230 ml of absolute ethanol. Refluxing time: 7 hours. Yld: 6.5 g (42%), m.p. 145-147 C. (ethyl acetate). NMR (DMSO-d6): delta=4.2 (2H, q); 4.6 (2H, s); 8.3 (2H, peak exchangeable with CF3 COOD); 8.7 (1H, m); 9.0 (1H, m).

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

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

Synthetic Route of 113305-94-5, These common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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.

A solution of tert-butyl 4-((2-chloro-5-iodopyridin-4-ylamino)methyl)piperidine-1- carboxyiate (Synthesis 170-B) (0.100 g, 0.22 mmol), dichlorobis(triphenyiphosphine)- palladium (II) (0.009 g, 0.01 mmol), trimethyl(2-methylbut-3-yn-2-yloxy)silane (0.048 mL, 0.24 mmol) and copper iodide (0.002 g, 0.01 mmol) was heated under microwave irradiation for 5 min at 120 0C. The crude mixture was concentrated in vacuo and filtered through a pad of silica, eluting with hexane / ethyl acetate (8 / 2), to give the crude product which was used without further purification. The crude pyridine (0.085 g, 0.163 mmol), 2-amino-4-cyanopyrazine (0.023 g, 0.195 mmol), Xantphos (0.015 g, 0.026 mmol), cesium carbonate (0.106 g, 0.326 mmol), dichlorobis(triphenylphosphine)- palladium (II) (0.012 g, 0.013 mmol) in dioxane (1.2 mL) were stirred at room temperature under nitrogen for 10 min, then heated under microwave irradiation for 60 min at 150 CC. The reaction mixture was purified by ion exchange on SCX-II acidic resin (2 g), eluting with methanol / dichloromethane (1 / 1 ), then 2M ammonia-methanol. The basic fractions were combined and solvent was removed in vacuo. The crude product was purified by preparative thin layer chromatography, eluting with methanol / dichloromethane (1 / 19), to give the title compound as a yellow solid (0.024 g, 27%).1H NMR (CDCI3, 500 MHz) delta 8.62 (s, 1 H), 8.44 (s, 1 H), 8.00 (s, 1 H), 7.17 (s, 1 H), 5.19 (t, 1 H, J = 5.8 Hz) 4.19-4.16 (m, 2H), 3.17 (t, 2H, J = 6.1 Hz), 2.72 (t, 2H, J = 11.3 Hz), 1.84- 1.75 (m, 3H), 1.66 (s, 6H), 1.47 (s, 9H), 1.27-1.21 (m, 2H), 0.90-0.84 (m, 1 H). LCMS (4) Rt = 2.17 min; m/z (ESI+) 492 [MH+].

Statistics shows that 5-Aminopyrazine-2-carbonitrile is playing an increasingly important role. we look forward to future research findings about 113305-94-5.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63286-28-2,Some common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, molecular formula is C4H5ClN4, 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.

Intermediate b (5.0 g, 0.034 mol) was added to triethyl orthoformate (50 mL), and the reaction was carried out at 80 C. The reaction time was monitored with a plate. The reaction liquid was directly filtered with cold suction, and the filter cake was washed with petroleum ether. After the cake was dried, 4.8 g of a yellow powder was obtained with a yield of 90.1%.

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

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Xu Shan; Liu Xiaobo; Zhang Qian; Zhou Lingjia; Han Haoyun; Yu Li; Zhou Hualan; Qiu Yufeng; (25 pag.)CN110467616; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 69816-35-9, These common heterocyclic compound, 69816-35-9, name is 6-(Trifluoromethyl)pyrazin-2-amine, 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.

1-(2-Chlorobenzoyl)-3-(6-trifluoromethyl-2-pyrazinyl)urea, having a melting point of about 179-180 C., from 1.5 g. of 2-amino-6-trifluoromethylpyrazine and 1.6 g. of 2-chlorobenzoylisocyanate.

Statistics shows that 6-(Trifluoromethyl)pyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 69816-35-9.

Reference:
Patent; Eli Lilly and Company; US4293552; (1981); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 72788-94-4,Some common heterocyclic compound, 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, molecular formula is C5H5ClN2O, 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 Intermediate 112A (2.00 g, 13.84 mmol) in CHCl3 (20 mL) was added active manganese dioxide (4.81 g, 55.3 mmol) and the resulting suspension was refluxed for 2 h. The reaction mixture was cooled to ambient temperature, filtered through Celite and washed with CHCl3 (200 mL). The combined filtrates were washed with brine (200 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Redisep-24 g, 20-30 % EtOAc/ n-hexane) to obtain Intermediate 112B (1.00 g, 50.70%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 8.98 (d, J = 1.51 Hz, 1 H), 9.04 (d, J = 1.51 Hz, 1 H), 10.07 (s, 1 H). LCMS: The compound did not ionize well.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem