Tag: M.W=100-200

Reference of 939412-86-9, The chemical industry reduces the impact on the environment during synthesis 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, I believe this compound will play a more active role in future production and life.

A mixture of (trans)-2-((benzyloxy)carbonyl)-4-oxooctahydro-l H-pyrido [1 ,2-a] pyrazine-7-carboxylic acid (1.3 g, 3.9 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (840 mg, 4.7 mmol), HATU (2.2 g, 5.8 mmol) and TEA (1.6 g, 15.6 mmol) in DMF (20 mL) was stirred at 25 C for overnight. Then the reaction mixture was poured into water and extracted with EA (50 ml*3). The combined organic phase was washed with brine (100 mL), dried over Na2S04, concentrated under vacuum to give the crude residue, which was purified by silica gel column chromatography (PE/THF = 1/3) to give (trans)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4- oxohexahydro-1 H-pyrido [l ,2-a]pyrazine-2(6H)-carboxylate (600 mg, yield 35.3 %). 1H NMR (400MHz, CD3OD) delta= 8.52 (d, J=2.5 Hz, 1H), 8.33 (d, J=2.3 Hz, 1H), 7.40 – 7.29 (m, 5H), 5.15 (br. s., 2H), 4.77 – 4.67 (m, 1H), 4.12 (br. s., 1H), 3.96 – 3.85 (m, 1H), 3.48 (br. s., 2H), 2.71 (t, J=12.5 Hz, 1H), 2.52 – 2.36 (m, 1H), 2.1 1 – 1.97 (m, 2H), 1.90 – 1.71 (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, (3-Chloropyrazin-2-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;; ; Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); 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 33332-29-5 as follows. name: 2-Amino-5-chloropyrazine

Step 2: Synthesis of 2,5-dichloropyrazine To a stirred solution of 5-chloropyrazin-2-amine (1 g, 7.751 mmol) in conc. HCl (10 mL) was added aq. solution sodium nitrite (1.1 g, 15.89 mmol) at -10 C. over a period of 1 h, stirred for 1 h 0 C. and then at RT for 2 h. Progress of reaction was monitored by TLC. After reaction completion reaction mass neutralised with 50% NaOH solution and extracted with DCM. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Crude was purified by silica gel (100-200 mesh) column chromatography using 2% ethyl acetate in hexane as eluent to yield 2,5-dichloropyrazine (0.59 g, 15%) as colourless oil. MS: 184.1 [M-1]

According to the analysis of related databases, 33332-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mankind Pharma Ltd.; Patil, Rakesh Ishwar; Verma, Jeevan; Shah, Dharmesh; Ali, Sazid; Bapuram, Srinivasa Reddy; Rai, Santosh Kumar; Kumar, Anil; (146 pag.)US2017/291910; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 22047-25-2, A common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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.

3-Hydrazinylbenzoisothiazole-1,1-dioxide (138mg; 0.7mmol) and acetylpyrazine (122mg; 1mmol) were mixed in isopropanol (25mL), and acetic acid (1mL) was added. The reaction mixture was then stirred at 75C for 2days. The volatile compounds were then evaporated under reduced pressure, and the residue was suspended in diethyl ether/petroleum ether mixture (1:1, v/v; 30mL). Solid material was filtered, washed with additional diethyl ether/petroleum ether mixture (1:1, v/v; 60mL) and dried at 50C under vacuum. 3-(2-(1-(Pyrazin-2- yl)ethylidene)hydrazinyl)-1,2-benzothiazole 1,1-dioxide (4) was obtained with a yield of 164mg (78%) as a yellowish solid. 1H NMR (DMSO-d6): 2.55 and 2.61 (2x s, 3H); 7.92 (m, 2H); 8.10 (s, 1H); 8.45 and 8.70 (2x m, 1H); 8.75 (m, 2H); 9.30 (s, 1H); 11.70 and 12.37 (2x bs, 1H) ppm. 13C NMR (DMSO-d6): delta 12.8 (13.6); 121.7 (121.6); 124.2; 126.7; 129.6; 133.8 (134.1); 133.9; 142.5; 143.0; 143.6 (143.8); 145.3 (145.0); 149.8 (149.7); 154.7 (159.9) ppm. ESI-MS (m/z): 302 [M+H]+. Elem. Anal. Calcd. for C13H11N5O2S: C, 51.82; H, 3.68; N, 23.24. Found: C, 51.80; H, 3.72; N, 23.26.

The synthetic route of 22047-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jakubek, Milan; Kejik, Zden?k; Kaplanek, Robert; Antonyova, Veronika; Hromadka, Robert; ?andrikova, Viera; Sykora, David; Martasek, Pavel; Kral, Vladimir; Bioorganic Chemistry; vol. 88; (2019);,
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. 4774-14-5, name is 2,6-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 4774-14-5

To a solution of 2,6-dichloropyrazine (2.0 equiv.) in 3:1 DME: 2M aqueous sodium carbonate (0.125 M) was added phenylboronic acid (1.0 equiv.) then PdCl2(dppf).DCM adduct (0.1 equiv.). The reaction was heated in the microwave at 120 C. for 15 minutes. The crude reaction mixture was diluted with ethyl acetate and washed with sat. aq. sodium bicarbonate then sat. NaCl. The organic phase was dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel column chromatography with heptanes to 30% ethyl acetate in heptanes to give 2-chloro-6-phenylpyrazine in 75% yield. LC/MS (m/z): 191.0 (MH+), Rt=1.00 min.

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 4774-14-5.

Reference:
Patent; Burger, Matthew; Ding, Yu; Han, Wooseok; Nishiguchi, Gisele; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225061; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 160252-31-3, These common heterocyclic compound, 160252-31-3, name is 1-(5-Chloropyrazin-2-yl)ethanone, 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 1-(5-chloropyrazin-2-yl)ethanone in ethanol (25 mL) was added to a solution of sodium ethoxide in ethanol at 0 C. The reaction mixture turned into a yellowish brown slurry. After it was stirred at 0 C. for 1 h, the reaction was quenched with saturated aqueous NH4Cl. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (0-30% EtOAc/hexanes) to give the title compound

The synthetic route of 160252-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Berger, Richard; Blizzard, Timothy A.; Campbell, Brian T.; Chen, Helen Y.; Debenham, John S.; Dewnani, Sunita V.; Dubois, Byron; Gude, Candido; Guo, Zack Zhiqiang; Harper, Bart; Hu, Zhiyong; Lin, Songnian; Liu, Ping; Wang, Ming; Ujjainwalla, Feroze; Xu, Jiayi; Xu, Libo; Zhang, Rui; (64 pag.)US2018/9796; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 74290-69-0, name is 5-Bromo-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 74290-69-0, Safety of 5-Bromo-6-methylpyrazin-2-amine

Step 1: Synthesis of 1-38.1To a solution of 1-35.4 (495 mg, 2.39 mmol) in THF (5ml) in a microwave vial is added hexamethyldistannane (0.55 ml, 2.64 mmol) followed by bis(triphenylphosphine)palladium(II) chloride (168 mg, 0.239 mmol). The reaction mixture is degassed with argon, capped, and stirred at 85 C for 16 hrs. R-32 (450 mg, 2.39 mmol) is added followed by tetrakis(triphenylphosphine)palladium (0) (276 mg, 0.239 mmol). The reaction vessel is degassed with argon, then capped and heated at 85 C for 16 hours. The reaction mixture is passed through a plug of Celite and rinsed with DCM. The filtrate is concentrated in vacuo and purified by flash chromatography (Si02, 0-5% MeOH/DCM) to afford the title intermdiate (160 mg); m/z 281.3 [M+l]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-6-methylpyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John, D.; LIU, Weimin; LO, Ho Yin; LOKE, Pui Leng; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee, M.; WO2012/40137; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 54013-07-9, name is 5-Methoxypyrazin-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. category: Pyrazines

Example 3 Preparation of 5-(6-((5-methoxypyrazin-2-yl)carbamoyl)-2-methylbenzofuran-4-yloxy)-N,N-dimethylpyrimidine-2-carboxamide (3) The title compound (3) was prepared by a method analogous to that described in Example 1 using 5-methoxypyrazin-2-amine and ethyl 4-(2-(dimethylcarbamoyl)-pyrimidin-5-yloxy)-2-methylbenzofuran-6-carboxylate (I-2a). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.49 (s, 3H), 2.99 (s, 3H), 3.15, (s, 3H), 3.98 (s, 3H), 6.28 (s, 1H), 7.51 (s, 1H), 7.89 (s, 1H), 7.94 (s, 1H), 8.30 (s, 1H), 8.50 (s, 2H), 9.17 (s, 1H). m/z=449.1 (MH+)

The synthetic route of 5-Methoxypyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2010/234285; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, 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. COA of Formula: C4H4ClN3

6-Chloronicotinoyl chloride (1.00 g, 5.68 mmol) in dry DCM (4 mL) was added dropwise to an ice cold solution of 1 -methyl- 1,4-diazepane (648 mg, 5.68 mmol) and NEt3 (1.18 mL, 8.52 mmol) in dry DCM (16 mL). The mixture was allowed to attain rt and stirred for 2 hours. Saturated aq Na2CO3/water (1 : 1, 40 mL) was added and the mixture was extracted with DCM (2x 30 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated to1.33 g of a light brown oil. MS (ESI+) for C12H 16C1N3O m/z 254 (M+H)+. Part of the material (294 mg, 1.16 mmol) was added to 6-chloropyrazin-2-amine (150 mg, 1.16 mmol), palladiumacetate (13 mg, 0.06 mmol), (+/-)-BINAP (36 mg, 0.06) and K2CO3 (2.4O g, 17.4 mmol) in dry toluene (12 mL) and stirred at 120 0C for 1.5 hours. The solvent was evaporated and the crude material was extracted with water/brine (1 : 1; 50 mL) and EtOAc (2x 50 mL). The organic layers were combined and concentrated. The title compound was obtained after purification by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10, MeCN), as a light brown solid (55 mg). MS (ESI+) for C16H19C1N6O m/z 347 (M+H)+.HPLC 92percent(System A), 85percent(System B).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33332-28-4, its application will become more common.

Reference:
Patent; BIOVITRUM AB (PUBL); WO2007/147874; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6905-47-1, These common heterocyclic compound, 6905-47-1, name is 2-Amino-6-methoxypyrazine, 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.

Example 55 (3S)-2-(2R)-3-Cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-1-methyl-N-[6-(methyloxy)-2-pyrazinyl]-3-pyrazolidinecarboxamide 6-(methyloxy)-2-pyrazinamine (67.4 mg, 0.539 mmol). LC-MS (ES) m/e 435.4 (M+H)+.

Statistics shows that 2-Amino-6-methoxypyrazine is playing an increasingly important role. we look forward to future research findings about 6905-47-1.

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;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 27398-39-6, name is 3-Chloropyrazine-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 27398-39-6, category: Pyrazines

To a suspension of sodium hydride (278 mg, 6.95 mmol, 60percent in oil) in DMF (10 mL) was added lH”-pyrazole (279 mg, 4.11 mmol) and the resulting mixture stirred at room temperature for 30 mins. 3-Chloropyrazine-2-carboxylic acid (500 mg, 3.16 mmol) was added and the mixture was heated to 60 ¡ãC for 2 h. After cooling to room temperature, water (20 mL) was added and the mixture extracted with 5percent MeOH in DCM (3 x 20 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to give Intermediate E as a solid. LRMS m/z (M+H) 191.0 found, 191.0 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (0 pag.)WO2016/85784; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem