Month: June 2021

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 36070-80-1 as follows. Application In Synthesis of 5-Chloropyrazine-2-carboxylic acid

To a solution of 5-chloropyrazine-2-carboxylic acid (500 mg, 3.1 mmol) and methyl-6- aminohexanoate hydrochloride (688 mg, 3.71 mmol) in dichloromethane (15 mL) was added 1 -ethyl-3-(3-dimethylaminopropyl)carbodiimide (71 1 mg, 3.71 mmol, 1.2 equiv). The reaction was allowed to stir for 18 hours at room temperature and was then diluted with dichloromethane (75 mL) and washed with 1 N hydrochloric acid (15 mL). The layers were separated, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and the residue was purified by flash column chromatography over silica gel (gradient elution with 20%-70% ethyl acetate in heptane) to provide methyl 6-{[(5-chloropyrazin-2-yl)carbonyl]- amino}hexanoate, 20 (378 mg, 43%), as a white solid. LCMS (Protocol E): m/z 308.2

According to the analysis of related databases, 36070-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; DUSHIN, Russell George; ABRAMITE, Joseph A.; CASAVANT, Jeffrey M.; CHE, Ye; FILZEN, Gary Frederick; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; MOINE, Ludivine; O’DONNELL, Christopher John; ROBERTS, Lee; STARR, Jeremy; TUMEY, Lawrence N.; UCCELLO, Daniel P.; YOUNG, Jennifer; (135 pag.)WO2018/25168; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 446286-94-8, 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. 446286-94-8, name is 5-Bromo-N,N-dimethylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To asolution of dimethyl amino 3d (1370 mg, 6.82mmol) in drytetrahydrofuran (50 mL) under Ar at 80 C was slowly added1.57M n-butyllithium hydride (n-BuLi) in hexane (10.8 mL).After stirring for 60min at 80 C, to the mixture was addedN,N-dimethylformamide (DMF) (2.0 mL, 26mmol) and theresulting solution was allowed to warm to r.t. After stirring for1 h, to the reaction mixture was added water to decompose theexcess reducing agent. Further, to the mixed solution was addedwater followed by extraction with ethyl acetate (3 200 mL).The combined organic layers were dried over Na2SO4, filtered,and the solvents were removed under reduced pressure. Theresidue obtained was purified by silica gel column chromatography(hexane/ethyl acetate = 1/1) to yield arylaldehyde 4d (975 mg, 6.46mmol, 95%) as a light yellow solid: mp 112 C;IR (neat, , cm1): 2783, 1681, 1373, 1008; 1HNMR (500MHz, CDCl3) 9.91 (s, 1H), 8.69 (s, 1H), 8.08 (d, J = 1.1 Hz,1H), 3.26 (s, 6H); 13CNMR (126 MHz, CDCl3) 190.7, 155.5,144.3, 136.8, 129.4, 37.9; HR-ESI-MS: m/z: [M+ H]+ calculatedfor C7H10N3O, 152.0824; found, 152.0814.

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, 5-Bromo-N,N-dimethylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Saito, Ryohei; Kuchimaru, Takahiro; Higashi, Shoko; Lu, Shijia W.; Kiyama, Masahiro; Iwano, Satoshi; Obata, Rika; Hirano, Takashi; Kizaka-Kondoh, Shinae; Maki, Shojiro A.; Bulletin of the Chemical Society of Japan; vol. 92; 3; (2019); p. 608 – 618;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 24241-18-7, 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 24241-18-7 as follows.

Intermediate Example 1 – 1 : Preparation of 6,8-dibromo-imidazo[ 1 , 2-a]pyrazineTo a stirred suspension of 2-amino-3, 5-dibrompyrazine (427 g, 1688mmol) in water (6.4 L) / THF (482 mL), at rt was added bromacetaldehyde-diethylacetal (998 g, 5065 mmol) in one portion. After stirring under reflux for 4 h, the clear orange solution was stirred for an additional 15 h at rt. The suspension was filtered, and the remaining solid was washed with MeOH (2 L) and dried in vaccuo at 60 C to yield 6,8-dibromo-imidazo[1 ,2-a]pyrazine as an off-white solid (500 g, 107% with residual MeOH) : 1 H-NM (300 MHz, d6-DMSO): delta =9.02 (s, 1 H), 8.23 (d, 1 H), 7.89 (d, 1 H) ppm. UPLC-MS: RT = 0.80 min; m/z 277.9 [MH+]; required MW = 276.9.

According to the analysis of related databases, 24241-18-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80228; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 723286-79-1,Some common heterocyclic compound, 723286-79-1, name is tert-Butyl 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H16N4O2, 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 9.01 g (40.0 mmol) of 7- (tert-butoxycarbonyl)-5, 6,7, 8- tetrahydro [1, 2,4] triazolo [4, 3-a] pyrazine in 150 mL chloroform was added 6.72 g (80.0 mmol) of sodium bicarbonate. The system was cooled to 0 C and 7.11 g (40.0 mmol) OF N- bromosuccinimide was added. The reaction was stirred at 0 C for 15 min and at ambient temperature for 16 h. The reaction was diluted with dichloromethane and washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The crude product was purified by flash chromatography on a BIOTAGE system (silica gel, 4% methanol/ethyl acetate) to yield the title compound. LC/MS 303.0 and 305.0 (M+1).

The synthetic route of 723286-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, A new synthetic method of this compound is introduced below., Product Details of 24241-18-7

Example 54; Step 1; A suspension of 1 (3 g, 11.64 mmol) in 25% aq. NH4OH (15 mL) in sealed tube was heated at 110 C. for 16 h. After completion of reaction (reaction progress was monitored by TLC), the reaction mixture was partitioned between ethyl acetate-water (3×50 mL). The combined extracts were washed with saturated brine, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with 15% ethyl acetate-hexane to afford 2 as a yellow solid (2.1 g, 93%). MS m/z (ES): 189 (M+H)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; de Vicente Fidalgo, Javier; Hermann, Johannes Cornelius; Lemoine, Remy; Li, Hongju; Lovey, Allen John; Sjogren, Eric Brian; Soth, Michael; US2011/59118; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 233278-56-3, 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 233278-56-3 as follows.

Step 1: tert-Butyl 9-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-azaspiro[5.5]undecane-3-carboxylate Acetic acid (2.34 eq.) was added to a solution of tert-butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (1.122 mmol, 1 eq.) and 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (1.14 eq.) in methylene chloride (7 ml). Sodium triacetoxyborhydride (1.4 eq) was then added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride and sat. NaHCO3 solution. The aqueous phase was washed with methylene chloride (2*20 ml), and the combined organic phases were dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (silica, ethyl acetate/ethanol 10:1) to obtain the desired product. Yield: 62%

According to the analysis of related databases, 233278-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; US2010/249095; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4774-14-5, These common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, 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 a solution of tert-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 Na2504, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes-*hexanes:EtOAc 1:1) to yield tert-butyl (1-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C,2H,7C1N402 mlz 285.1 (M+H).

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (242 pag.)WO2017/23981; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 2423-65-6, A common heterocyclic compound, 2423-65-6, name is Pyrazine 1-oxide, molecular formula is C4H4N2O, 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: Synthesis of meso-substituted calixarenes 4a-f (general procedure). A 1.6 M solution of BunLi in hexane (1.44 mL, 2.3 mmol) was added to a vigorously stirred solution of TMEDA (0.43 mL, 2.9 mmol) in anhydrous THF (4 mL) cooled to -78 C. After 40 min of stirring, a solution of 25,26,27,28-tetramethoxycalix[4]arene (480.5 mg, 1.0 mmol) in anhydrous THF (5 mL) was added, the reaction mixture was warmed up to room temperatures and stirred for another 2 h. The solution of formed 2-lithium-25,26,27,28-tetramethoxycalix[4]arene (1) was cooled to -78 C, and a solution of the corresponding azine N-oxide 2a-f (2.0 mmol) in anhydrous THF (6 mL) was added. The reaction mixture was stirred at room temperature for 1 h, followed by the addition of AcCl (0.14 mL, 2.0 mmol). The mixture was concentrated at reduced pressure. The residue was subjected to column chromatography on SiO2, the eluate was concentrated dry in vacuo.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Varaksin; Chupakhin; Charushin; Khlamkin; Utepova; Russian Chemical Bulletin; vol. 64; 5; (2015); p. 1093 – 1096; Izv. Akad. Nauk, Ser. Khim.; 5; (2015); p. 1093 – 1096,4;,
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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1458-01-1

Preparation 1Methyl 3,5-diamino-6-r2-(trifluoromethoxy)phenyllpyrazine-2-carboxylateMETHOD AMethyl 3,5-diamino-6-chloropyrazine~2-carboxylate (1.62 g, 8.0 mmol) was combined with 2-(trifluoromethyl)phenylboronic acid (3.29 g: 16.0 mmol), palladium tetrakistriphenylphosphine (0.924 g, 0.80 mmol) and cesium carbonate (2.61 g, 8.0 mmol) and suspended in a mixture of 1 ,4-dioxane (30 ml) and water (15 ml). The reaction was sealed and heated to 750C for 4 hours before cooling to room temperature. Water (150 ml) was added and the 1 ,4-dioxane removed in vacuo. The precipitate formed was collected by filtration and dried. The brown solid was triturated with dichloromethane:methanol, then purified by silica gel column chromatography eluting with 95:5 dichloromethane:methanol to afford the title compound as a yellow solid (1.66 g, 63percent yield).1HNMR (d6-DMSO): 3.7 (s, 3H), 6.59 (br s, 2H), 7.10 (br s, 2H), 7.41-7.64 (m, 4H) LCMS Rt=8.64 min MS m/z 329 [MH]+

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 1458-01-1.

Reference:
Patent; PFIZER LIMITED; WO2008/135830; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 32974-92-8, 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. 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

mixture of 3-ethyl-2-acetylpyrazine (1.50 g, 10 mmol) andsemicarbazide hydrochloride (1.11 g, 10 mmol) in ethanol (30 ml)were stirred for 4 h at room temperature. The white solid wasprecipitated, then filtered and washed three times by cold ethanol.Yield: 1.78 g (86%).

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-Ethylpyrazin-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Hong; Ma, Xiu-Qin; Lv, Yan-Yun; Jia, Lei; Xu, Jun; Wang, Yuan; Ge, Zhi-Jun; Journal of Molecular Structure; vol. 1109; (2016); p. 146 – 153;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem