Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 345311-03-7, name is tert-Butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-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 345311-03-7, Product Details of 345311-03-7

7-Bromo-N-(3-ethyl-l-((6-methylpyridin-2-yl)methyl)-lH-indazol-4- yl)imidazo[l,2-a]pyridine-3-carboxamide (prepared as in Example 127, Step A; 50 mg, 0.10 mmol) in DMF (4 mL) was added tert-butyl 5,6-dihydroimidazo[l,2-a]pyrazine-7(8H)- carboxylate (68 mg, 0.31 mmol), Pd(PPh3) 4 (12 mg, 0.01 mmol), palladium diacetate (2.3 mg, 0.010 mmol) and K2C03 (42 mg, 0.31 mmol). The reaction mixture was purged with argon and the reaction vial was sealed and the mixture was heated to 140 C for 3 hours. The mixture was cooled to ambient temperature and diluted with DCM (20 mL). The solution was washed with H20, dried (Na2S04) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10: 1 :0.1) to provide the final product (14 mg). MS (ES+APCI) m/z = 532 (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, tert-Butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BRADLEY, Michael; DELISLE, Robert Kirk; HENNINGS, D. David; KENNEDY, April L.; MARMSATER, Fredrik P.; MEDINA, Matthew; MUNSON, Mark C.; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2011/79076; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, 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. category: Pyrazines

A solution of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (1.2 g, 5.92 mmol, 1.00 equiv) and 2-bromo-1,1-dimethoxyethane (2 g, 11.83 mmol, 2.00 equiv) in acetonitrile (20 mL) was irradiated with microwave for 40 min at 120¡ã C. After completion the resulting solution was concentrated under vacuum and the residue was purified by a silica gel column eluting with dichloromethane/methanol (10:1) to give the title compound (300 mg, 22percent) as a yellow solid. LC-MS (ES, m/z): 227 [M+H]+.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 117719-17-2, 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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

5-bromo-3-morpholin-4-yl-pyrazin-2-ylamine (100 mg, 1 eq) was suspended in DME (1 mL) and 1-(4-methoxybenzyl)-4-chloropiperidine-2,3-dione, 1-11 , (125 mg, 1.2 eq) was added. The reaction mixture was heated in a sealed tube at 90C for 17 h. On cooling, the mixture was purified by automated chromatography (Biotage, eluent: 30% to 60% EtOAc in Cyclohexane) to give the expected product 1-10 (150 mg, 60% yield) which was used in next reaction step without further purification, as a brown solid.

The synthetic route of 5-Bromo-3-morpholinopyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONC&Oacgr;LOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ ARISTEGUI, Sonsoles; GONZALES CANTALAPIEDRA, Esther; HERNANDEZ HIGUERAS, Ana Isabel; VARELA BUSTO, Carmen; WO2011/36461; (2011); 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 1196152-38-1 as follows. name: 2-Bromo-5-(trifluoromethyl)pyrazine

A 4 mL vial, equipped with a magnetic stir bar, was charged with N-(4- aminobicyclo[2.2.2]octan- 1 -yl)-2-(4-chloro-3-fluorophenoxy)acetamide hydrochloride (Example 1C, 28.2 mg, 0.078 mmol), 2-bromo-5-(trifluoromethyl)pyrazine (Anichem, CAS 1196152-38-1, 21.15 mg, 0.093 mmol), N,N-diisopropylethylamine (0.0542 mL, 0.310 mmol), and dimethylformamide (0.5 mL). The vial was sealed with a pressure relief septum cap, and the reaction mixture was stirred at 90 C for 16.5 hours. The reaction mixture was allowed to cool to ambient temperature, and the septum cap was removed. The vial contents were partitioned between ethyl acetate and water. The aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed twice with brine, then dried (MgSO/t) and filtered. The filtrate was concentrated under reduced pressure to give a brown oil that was purified by column chromatography on an Analogix IntelliFlash-310 (Isco RediSep 12 g silica gel cartridge, 100% heptane to 60:40 heptane/ethyl acetate). Fractions containing the title compound were combined and concentrated under reduced pressure to give the title compound as a white solid, but there was still contamination, so a second column was run (Practichem 2 x 4 g silica gel cartridges, 100% dichloromethane to 90: 10 dichlorome thane/ethyl acetate). Fractions containing the title compound were combined and concentrated under reduced pressure to give the title compound as a white solid that was dried overnight in a vacuum oven at 50 C (3.5 mg, 9.5% yield). JH NMR (CDC13) delta ppm 8.28 (s, 1H), 7.80 (d, J = 1.4 Hz, 1H), 7.36-7.29 (m, 1H), 6.74 (dd, J = 10.3, 2.8 Hz, 1H), 6.66 (ddd, J = 8.9, 2.9, 1.3 Hz, 1H), 6.11 (s, 1H), 4.71 (s, 1H), 4.34 (s, 2H), 2.19-2.05 (m, 12H); MS (+ESI) m/z = 473 (M+H)+; (-ESI) m/z = 471 (M- H)

According to the analysis of related databases, 1196152-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 25710-18-3, These common heterocyclic compound, 25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, 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.

[0450] Example 15 [0451 ] Synthesis of 3 -(4-(2,5 -dichlorobenzyl)piperazin- 1 -yl)-N-(pyridin-3 -yl)pyrido [2,3 – b]pyrazin-2-amine, 2,2,2-trifluoroacetic acid salt [0452] Step 1 : 2-chloro-3-(4-(2,5-dichlorobenzyl)piperazin-l-yl)pyrido[2,3-b]pyrazine [0453] To a solution of 2,3-dichloropyrido[2,3-b]pyrazine (21 mg, 0.105 mmol) and l-(2,5- dichlorobenzyl)piperazine, HC1 (31.0 mg, 0.1 10 mmol) in dioxane (350 mu) was added N- ethyl-N-isopropylpropan-2-amine (56.8 mu, 0.325 mmol) dropwise at RT. The resulting mixture was stirred at RT overnight and HPLC purification yielded the title compound as a yellow solid.

The synthetic route of 25710-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVOY THERAPEUTICS, INC.; HITCHCOCK, Stephen; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; KIKUCHI, Shota; MACKLIN, Todd; HOPKINS, Maria; WO2014/28479; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 76537-18-3, 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 76537-18-3 as follows.

Zinc dust (activated by the procedure found in WO2011/143365, the disclosure of which is incorporated herein by reference in its entirety) (0.627 g, 9.59 mmol) was charged to a dry flask and suspended in DMA (2.5 mL). 1,2-Dibromoethane (0.031 mL, 0.36 mmol) and TMSCl (0.092 mL, 0.72 mmol) were added and the reaction was stirred for 25 min. tert-Butyl 3-iodoazetidine-1-carboxylate (2.04 g, 7.20 mmol, Oakwood) in DMA (6.0 mL) was added slowly to the mixture which was immersed in a water bath to keep the temperature below 65 C. The mixture was stirred for 1 hour and was degassed by bubbling a stream of nitrogen through the mixture for 5 minutes. (0976) A separate flask was charged with 3-bromo-5-chloropyrazin-2-amine (0.50 g, 2.4 mmol, D-L Chiral Chemicals), dichloro[1,1?-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.118 g, 0.144 mmol) and copper(I) iodide (0.057 g, 0.30 mmol). DMA (6.0 mL) was added, and the mixture was degassed by bubbling a stream of nitrogen through the mixture for 5 minutes. The solution containing the organozinc in DMA was added, excluding any remaining zinc solids. The reaction mixture was then heated at 80 C. for 30 min. Upon cooling to room temperature, the reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted with two additional portions of EtOAc. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-100% EtOAc in hexanes to afford product (0.62 g, 90%). LCMS calculated for C12H18ClN4O2(M+H)+: m/z=285.1, found: 285.1. 1H NMR (400 MHz, CDCl3) delta 7.96-7.90 (s, 1H), 4.78-4.65 (s, 2H), 4.35-4.22 (m, 4H), 3.79-3.69 (p, J=7.4 Hz, 1H), 1.48-1.44 (s, 9H).

According to the analysis of related databases, 76537-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Incyte Corporation; Shepard, Stacey; Combs, Andrew P.; Falahatpisheh, Nikoo; Shao, Lixin; (96 pag.)US2019/276435; (2019); 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H2BrF3N2

Description 67: 1,1-dimethylethyl (lR,4S,6R)-4-({[5-(trifluoromethyl)-2- pyrazinyl]oxy}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate (D67); To a solution of 1,1-dimethylethyl (lR,4S,6R)-4-(hydroxymethyl)-3- azabicyclo[4.1.0]heptane-3-carboxylate D20 (120 mg) and 2-bromo-5- (trifluoromethyl)pyrazine D66 (120 mg) in DMF (4 ml) at 00C (ice bath) was added NaH (31.7 mg, 0.792 mmol) (gas evolution). The reaction mixture was slowly warmed to room temperature and stirred at room temperature for 1 hour. The reaction was quenched by a slow and careful addition of a saturated aqueous solution of NaHCO3 (40 ml). The organic phase was extracted with DCM (3×50 ml); the joined organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to give the crude material. This was purified by Silica Chromatography (Biotage SP – column size 25 g) using Cy/EtOAc 90:10 as eluent. The appropriate fractions were concentrated to obtain the title compound D67 (62 mg).UPLC (Basic GEN_QC): rt = 1.07 minutes, peak observed: 374 (M+l) C17H22F3N3O3 requires 374.

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 1196152-38-1.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 622392-04-5, These common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, 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.

Preparation 67: iert-Butyl (2S)-2-{4-[4-(5-bromopyrazin-2-yl)phenyl]-1 H-imidazol-2-yl}pyrrolidine-1- carboxylateMethod A:Potassium phosphate (7.39 g, 34.81 mmol) was added to a stirred solution of 2-bromo-5-iodopyrazine obtained from Preparation 10 (7.65 g, 17.41 mmol) and tert-butyl (2S)-2-{4-[4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)phenyl]-1 H-imidazol-2-yl}pyrrolidine-1 -carboxylate obtained from Preparation 3 (6.45 g, 22.63 mmol) in a mixture of 1 ,4-dioxane : water (3:7, 500 mL). The mixture was degassed for 20 minutes after which time tetrakis(triphenylphosphine)palladium (0) (2.00 g, 1 .74 mmol) was added and the reaction heated to 90C for 2 hours. After this time, the reaction mixture was cooled to room temperature and poured into a saturated solution of sodium bicarbonate (500 mL). The product was extracted with ethyl acetate (3 x 500 mL). The combined organic layers were dried over sodium sulphate and the solvent was removed under reduced pressure to a brown crude oil. The crude product was purified by flash chromatography (ethyl acetate:dichloromethane, 50 : 50 to 100 : 0) to give the title compound as a pale yellow solid (5.56 g).LCMS: (run time = 4.5 minutes, System J): Rt = 2.22 minutes; m/z 470.19 and 472.07 [MH+]H NMR (400 MHz, CD3OD) delta = 8.95 (s, 1 H), 8.75 (s, 1 H), 8.1 (d, 2H), 7.85 (d, 2H), 7.50-7.40 (m, 1 H), 4.90- 4.80 (m, 1 H), 3.75-3.65 (m, 1 H), 3.55-3.45 (m, 1 H), 2.40-2.30 (br. m, 1 H), 2.10-1.90 (m, 3H), 1.25 (s, 9H)

The synthetic route of 622392-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; TRAN, Thien Duc; WAKENHUT, Florian; WO2011/154871; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

173290-17-0, name is Methyl 3-iodopyrazine-2-carboxylate, 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: C6H5IN2O2

Example 5 Preparation of Methyl 3-trifluoromethyl-pyrazine-2-carboxylate (8) To methyl 3-iodopyrazine-2-carboxylate (7) (10 g, 37.88 mmol) in DMF (Volume: 300 mL) was added methyl chlorodifluoroacetate (27 g, 0.189 mol), potassium fluoride (13.2 g, 0.227 mol), and copper chloride (22.47 g., 0.227 mol). The reaction was heated at 120 C. for 12 h. The reaction mixture was poured into ethyl ether (1000 ml) and washed with brine (3*300 ml), dried over MgSO4 before the solvent was removed. The residue was loaded onto a silica column and was eluted using ethyl acetate/hexanes gradient to afford the title compound (3.19 g, 41%) as an amber oil: 1H NMR (400 MHz, CDCl3) delta 8.85 (d, J=5.4 Hz, 1H), 8.82 (d, J=5.4 Hz, 1H), 4.05 (s, 3H); EIMS m/z 206.

The synthetic route of 173290-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; US2011/301178; (2011); 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. 426829-61-0, name is N-Benzyl-6-chloropyrazin-2-amine, A new synthetic method of this compound is introduced below., Computed Properties of C11H10ClN3

Step 2: N-Benzyl-6-(1-Piperazinyl)-2-Pyrazinamine. A mixture of the product from step 1 above (1.25 g, 5.7 mmol), piperazine (1.0 g, 11.6 mmol), and K2CO3 (1.0 g, 7.3 mmol) in dioxane (3 mL) was heated at 160 C. for 11 h in a sealed pyrex flask. The reaction mixture was diluted with dichloromethane, filtered and concentrated in vacuo. The red-brownish residue was dissolved in a small volume of CHCl3/MeOH (9:1) and purified by silica gel chromatography (15 *4 cm) using CHCl3/MeOH (95:5, followed by 9:1) as eluent. The free base was obtained as a brownish solid (0.9 g, 3.33 mol) that was redissolved in methanol (10 mL). Maleic acid (0.45 g, 3.83 mmol) in methanol (5 mL) was added and the salt was precipitated out by addition of ether. The salt was recrystallized from MeOH-ether and finally converted back to the free base by alkalinization (10% aqueous Na2CO3) and extraction with ether (5*60 mL). The combined ether layers were dried (K2CO3), filtered and concentrated. This furnished 0.36 g (23%) of the title compound as a light yellow powder. HRMS m/z calcd for C15H19N5(M)+269.1640, found 269.1641. Anal. (C15H19N5) C, H, N.

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; Nilsson, Bjorn M.; US2002/147200; (2002); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem