Tag: M.W=100-200

Reference of 22047-25-2, 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. 22047-25-2, name is Acetylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Preparation of 4,4-difluoro-1-(2-pyrazinyl)-butane-1,3-dione Ethyl difluoroacetate (2.23 g, 18 mmol) was placed in a 100 mL round bottom flask and dissolved in ether (10 mL). To the stirred solution was added 25 weight % sodium methoxide (4.68 g, 22 mmol) followed by acetylpyrazine (2.00 g, 16 mmol). After two hours stirring at room temperature, a precipitate formed and THF (10 mL) was added to the reaction. The reaction was stirred an additional 25.9 hours, then treated with 3N HCl (10 mL). The organic layer was collected, washed with brine (20 mL), dried over MgSO4, and concentrated in vacuo and recrystallized from methylene chloride/isooctane to give the diketone as a brown solid (2.23 g, mp 103-110 C., 68%). 1 H NMR (CDCl3) 300 MHz 14.00 (br s, 1H), 9.31 (d, J=1.4 Hz, 1H), 8.76 (d, J=2.4 Hz, 1H), 8.68 (dd, J=1.4 Hz 2.4 Hz, 1H), 7.20 (s, 1H), 6.03 (t, J=54.0 Hz, 1H); 19 F NMR (CDCl3) 300 MHz: -127.16 (d); M+200.

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, Acetylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G.D. Searle & Co.; US5466823; (1995); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41110-29-6, name is Methyl 3-methylpyrazine-2-carboxylate, 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 41110-29-6, category: Pyrazines

To a stirred solution of the product of Step A (0.9 g, 5.9 mmol) in MeOH (20 mL) was added hydrazine hydrate (1.5g, 23.7 mmol) at RT. The mixture was stirred at 60 overnight. The mixture was concentrated and the residue was dissolved into EtOAc (30 mL) . The organic phase was washed with brine, dried over Na 2SO 4 and concentrated under reduced pressure. The residue (460 mg, yield: 51.1%) was used into next Step directly. MS: M/e 153 (M+1) +.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 914452-71-4, A common heterocyclic compound, 914452-71-4, name is 2-Bromo-6-methylpyrazine, molecular formula is C5H5BrN2, 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.

General procedure: To a stirred solution of 1 (100mg, 577.99mumol), 2 (168mg, 924.79mumol) in DMF:water (5mL, 1:1), it was added Na2CO3 (141 mg, 1.33 mmol) and 1 mg of PdNP at room temperature. The resulting reaction mixture was heated at 100 C for 15 min, after completion of reaction reaction mass was cooled to room temperature, diluted with H2O (10 mL) and extracted with EtOAc (3×15 mL). The combined organic layer was washed with brine solution, dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude compound, which was triturated with pet ether to delivered 3 (120 mg, 90%) as off-white solid. 1H NMR (500 MHz, CDCl3) delta: 8.79 (d, J = 5.0 Hz, 1H), 8.34 (d, J = 5.0 Hz, 1H), 7.70 – 7.51 (m, 1H), 7.04 – 6.92 (m, 1H), 4.09 – 3.89 (m, 2H), 2.66 – 2.59 (m, 1H); 13C NMR (126 MHz, CDCl3) delta 153.01, 151.40, 150.56, 149.51, 141.92, 138.57, 129.50, 119.66, 111.23, 109.83, 56.02, 56.01, 21.76; LC-MS (ESI): 231.16 (M+H).

The synthetic route of 914452-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bendre, Ameya D.; Kodam, Kisan M.; Patil, Viraj P.; Terdale, Santosh S.; Waghmode, Suresh B.; Journal of Organometallic Chemistry; vol. 909; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 77112-52-8,Some common heterocyclic compound, 77112-52-8, name is Ethyl imidazo[1,2-a]pyrazine-2-carboxylate, molecular formula is C9H9N3O2, 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.

Procedure for step-3 :To a well stirred suspension of the ester obtained from step-1 (1Og, 52.3 ?imol) in dioxane (400 ml) was added lithium borohydride (2 eqv) at 25C and the resulting reaction mixture was allowed to stir at the same temperature for 10 minutes. It was then warmed to 60C and kept at this temperature for for 20 minutes ( . Higher temperature and more reaction time reduce the yield and quality of reaction) . Reaction mixture was then cooled to 0C, acidified with IN HCl and dioxane was completely evaporated under reduced pressure. Residue was taken in dichloromethane (200 ml) , TEA ( 4eqv) and Boc-anhydride ( 1.2 eqv) was added to it and the resulting reaction mixture was allowed to stir at 250C for 16 hrs . Organic layer was washed with water and brine and finally dried over sodium sulfate. Evaporation of organic layer gave the crude product which was purified by column chromatography (70% ethyl acetate in hexane) . Yield : 27%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl imidazo[1,2-a]pyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; WO2009/90055; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 59489-39-3, 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 59489-39-3 as follows.

3,5-dibromo-6- chloropyrazin-2-amine (Rz = Cl) was prepared according to Organic Letters, 17(15), 3888- 3891; 2015. 6-amino-3,5-dibromopyrazine-2-carbonitrile (Rz = CN) was prepared as follows.6-Aminopyrazine-2-carbonitrile (ig, 8.3 mmol) was dissolved in dichloromethane (15 mL). To this solution, NBS (2.96g, 16.65 mmol, 2 eq.) was added, and the reaction mixture was stirred at room temperature overnight (16 h). The reaction mixture was poured into water and extracted with dichloromethane, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified using silica gel chromatography with Heptane/EtOAc as eluent providing 6-amino-3,5-dibromopyrazine-2-carbonitrile (Rz = CN)

According to the analysis of related databases, 59489-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROMEGA CORPORATION; HALL, Mary; KIRLAND, Thomas; MACHLEIDT, Thomas; SHAKHMIN, Anton; WALKER, Joel, R.; (141 pag.)WO2018/22865; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

To 2-aminomethyl-3-chloropyrazine hydrochloride (content 80%; 4.44 mmol, 1 g) and N,N- diisopropylethylamine (17.77 mmol, 3.10 ml) in dichloromethane (20 ml) under N2 at 0C was added N- methylpiperazin-4-carbamoyl chloride hydrochloride (4.89 mmol, 0.973 g). After stirring at room temperature for 18 hours water was added and the mixture extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Purification by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) gave N-((3-chloropyrazin-2-yl)methyl)-4-methylpiperazine-1 -carboxamide (513 mg).

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 912773-24-1,Some common heterocyclic compound, 912773-24-1, name is 6-Bromoimidazo[1,2-a]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.

A 20 mL Biotage microwave vial loaded with 6-bromoimidazo[1,2-a]pyrazine (120 mg, 0.606 mmol), pyridin-4-ylboronic acid (82 mg, 0.667 mmol), Pd(PPh3)4 (63 mg, 0.055 mmol), and NaHCO3 (204 mg, 2.424 mmol), was capped, purged with argon, then injected with degassed dioxane: H2O (3.73 mL: 0.93 mL, 4:1 v/v), and heated to 140 for 40 min in a Biotage Microwave Reactor. The reaction was cooled, diluted with DCM, filtered through celite, concentrated, dryloaded onto silica gel and purified on a 12 g silica gel column (DCM/MeOH, 0-8%), affording 6-(pyridin-4-yl)imidazo[1,2-a]pyrazine 66 as a white solid (85 mg, 0.433 mmol, 72% yield, 8% MeOH). 1H NMR (DMSO) delta: 9.45 (d, J=1.5 Hz, 1H), 9.21 (dd, J=1.5, 0.7 Hz, 1H), 8.70 (d, J=6.2 Hz, 2H), 8.18 (s, 1H), 8.01 (d, J=6.2 Hz, 2H), 7.91 (d, J=1.1 Hz, 1H). 13C NMR (DMSO) delta: 150.78, 144.04, 143.05, 140.21, 136.70, 135.33, 120.33, 119.05, 116.10.

The synthetic route of 912773-24-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arizona Board of Regents on Behalf of the University of Arizona; Hulme, Christopher; Foley, Christopher; (166 pag.)US2020/39989; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 41110-29-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 41110-29-6 name is Methyl 3-methylpyrazine-2-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of mixture of methyl 5-chloro-3-methylpyrazine-2-carboxylate and methyl 6-chloro-3-methylpyrazine-2-carboxylate (8.6 g, 46.1 mmol) and hydrogen peroxide urea adduct (8.1 g, 86 mmol) in DCM (100 mL) was added 2,2,2-trifluoroacetic anhydride (10.89 ml, 78 mmol) dropwise. The resulting mixture was stirred at RT for 2 h, during which LCMS indicated complete transformation to the desired products. The reaction was diluted with CH2Cl2and quenched with water. The aqueous layer was back-extracted with CH2Cl2 (2¡Á). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo to give crude products 5-chloro-2-(methoxycarbonyl)-3-methylpyrazine 1-oxide and 5-chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide (8.83 g, 43.6 mmol, 95% yield). MS m/z=203.0 [M+H]. Calculated for C7H7ClN2O3: 202.0. The mixture of the crude products were used without further purification.

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

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

(e) (2S,5R)-benzyl5-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-(hydroxymethyl)piperidine-1-carboxylate To a solution of (3S,6S)-1-((benzyloxy)carbonyl)-6-(hydroxymethyl)piperidine-3-carboxylic acid (0.78 g, 2.66 mmol) in 20 mL of DMF was added HATU (1.21 g, 3.2 mmol). After stirring for 30 min under N2, (3-Chloro-pyrazin-2-yl) methanamine hydrochloride (0.48 g, 2.66 mol) and Et3N (0.8 g, 7.98 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours under N2. The mixture was partitioned between EA and water. The organic layer was washed with 1 N HCl and water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford (2S,5R)-benzyl 5-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-(hydroxymethyl) piperidine-1-carboxylate (0.7 g, 63.0% yield). 1HNMR (400 MHz, CD3OD): delta=8.50?8.54 (m, 1H), 8.35 (d, J=2.4 Hz, 1H), 7.31?7.41 (m, 5H), 5.16 (s, 2H), 4.63 (s, 2H), 4.34?4.38 (m, 1H), 4.21?4.25 (m, 1H), 3.72?3.77 (m, 1H), 3.63?3.67 (m, 1H), 3.01?3.07 (m, 1H), 2.46?2.54 (m, 1H), 1.80?1.93 (m, 3H), 1.61?1.71 (m, 1H). MS (ESI): M/Z (M+1): 419.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Chloropyrazin-2-yl)methanamine hydrochloride, its application will become more common.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486460-20-2, name is 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine, 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 486460-20-2, Application In Synthesis of 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine

To a solution of 3-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyrazine (1.60 g) in metanol (20 mL) was added a catalytic amount of Pd/C. The suspension was stirred under H2 for 5 h, and then filtered. The filtrate was concentrated in vacuo to give a residue, which was used for next step without further purification.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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