Category: 69214-33-1

69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, 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

Example A15Mixture of 3-bromo-8-chloro-imidazo[1,2-c]pyrazine and 3,8-dibromo-imidazo[1,2-a]pyrazine N-Bromosuccinimide (2.0 g, 11.6 mmol) was added to a stirred solution of intermediate 3 (1.78 g, 11.58 mmol) in DCM (50 ml). The mixture was stirred at RT for 2 h. and then diluted with further DCM and washed with a saturated solution of sodium carbonate. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield a 72/28 mixture of 3-bromo-8-chloro-imidazo[1,2-c]-pyrazine and 3,8-dibromo-imidazo[1,2-a]pyrazine (intermediate 15) (5.89 g, 99%) as white solid.

The synthetic route of 69214-33-1 has been constantly updated, and we look forward to future research findings.

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. 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Formula: C6H4ClN3

Step 2: 3-Bromo-8-chloroimidazo[l,2-a]pyrazine[0314] A solution of 8-chloroimidazo[l,2-a]pyrazine (15g, 97.4 mmol) in DCM (300 mL) was treated with NBS (19. Ig, 108 mmol) at room temperature and stirred at this temperature for overnight. The reaction was monitored by TLC. After this time, the resulting solution was diluted with 200 mL DCM and washed with saturated solution of Na2CO3 (2×150 mL), and brine (1×150 mL). Organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the crude product that was purified by a silica gel column chromatography eluted with ethyl acetate in petroleum ether (1:2) to give 3-bromo-8-chloroimidazo[l,2-a]pyrazine (9.5g, 42%) as yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.04 (IH, d, J = 4.6 Hz), 7. 84 (s, IH), 7.82 (2H, d, J = 4.6 Hz).

The synthetic route of 69214-33-1 has been constantly updated, and we look forward to future research findings.

69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, 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. name: 8-Chloroimidazo[1,2-a]pyrazine

Example 2 – Synthesis of A/-(3-(8-(3-fluorophenylamino)imidazori,2-a1pyrazin-3- vDphenvDacetamide (Compound 160)3-Bromo-8-chloroimidazo[ 1 ,2-a”|pyrazine[00239] Bromine (1.42 mL, 27.72 mmol) was added to a suspension of 8- chloroimidazo[l,2-a]pyrazine (2.83 g; 18.48 mmol) in glacial acetic acid (55 mL) and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was then concentrated in vacuo and the resulting residue was taken up in DCM/methanol (9:1), subsequently washed with saturated aqueous sodium bicarbonate solution (2 x 70 mL), IM sodium thiosulfate (70 mL), brine (70 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (3.397 g, 79%) as a light brown/golden solid. 1H NMR (d6-DMSO): 8.49(IH, d, J4.6), 8.04 (IH, s), 7.89-7.84 (IH, br m).[00240] The use of Br2/acetic acid could give partial bromination, along with partial chloride displacement by bromide, giving a mixture of 4 possible products A:B:C:D in a1 :2: 1 : 1 mixture. The dihalo species C and D were separated from the monohalo analogues A and B so the final compound was a mixture of two dihaloimidazopyrazines. This product composition could alter on a larger scale.X = Cl, A X = Cl, CX = Br, B X = Br, DA:B:C:D = 1 :2:1 :1

The synthetic route of 69214-33-1 has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 69214-33-1, name is 8-Chloroimidazo[1,2-a]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. Quality Control of 8-Chloroimidazo[1,2-a]pyrazine

A vial containing tert-butyl 2,8-diazaspiro[4.5]decane-8-carboxylate (263 mg, 1.09 mmol), 8- chloroimidazo[l,2-a]pyrazine (168 mg, 1.09 mmol) and triethyl amine (152 uL, 1.09 mmol) in THF (5.4 mL) heated to 50C for 4 hours. The reaction was cooled and concentrated to give the crude material, which was purified via MPLC (50-100% EtOAc/hexanes) to afford the title compound. LC-MS (357, m/z): 358 [M+l]+.

The synthetic route of 8-Chloroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Adding a certain compound to certain chemical reactions, such as: 69214-33-1, name is 8-Chloroimidazo[1,2-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 69214-33-1, Quality Control of 8-Chloroimidazo[1,2-a]pyrazine

To the solution of compound 9 (6.47 g, 42.13 mmol) indichloromethane (140 ml) N-bromosuccinimide (7.50 g,42.13 mmol) was added and the mixture was stirred at roomtemperature for 3 h. The reaction mixture was diluted withdichloromethane and stirred with 10% aqueous sodium carbonatesolution for 1 h before the layers were separated. The organic layerwas washed with water (2), dried over sodium sulphate, filteredand concentrated under reduced pressure. The crude product was triturated with diisopropyl ether and filtered to give the titlecompound (14.40 g)

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:
Article; Garamvoelgyi, Rita; Dobos, Judit; Sipos, Anna; Boros, Sandor; Illyes, Eszter; Baska, Ferenc; Kekesi, Laszlo; Szabadkai, Istvan; Szantai-Kis, Csaba; Keri, Gyoergy; Oerfi, Laszlo; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 623 – 643;,
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. 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4ClN3

To a solution of 8.-chioroimidazo[i ,2a1pyrazine (200 mg, I .3 mmol) in MeCN/DCE (3 mL/1,5 mL) was added N1S (293 mg, I .3 mmol) at RT. The mixture was refluxed overnight. TLC (50% EtOAc in petroleum ether) indicated that starting material disappeared, the mixture was poured into water (10 mL), extracted with EtOAc (10 mL x 3). The combined organic layerwas washed with water (1 0 mL) and brine (1 0 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (200 mg) as a brown solid, LRMS m/z (M-f-H) 279.1, 281.1 found, 279.1, 281.1 required.

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; 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

Adding a certain compound to certain chemical reactions, such as: 69214-33-1, name is 8-Chloroimidazo[1,2-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 69214-33-1, Quality Control of 8-Chloroimidazo[1,2-a]pyrazine

N-(4-(Imidazo[1,2-a]pyrazin-8-ylamino)phenyl)-4-methylbenzenesulfonamide (35) All glassware was dried and purged with Arprior to use. Pd2(dba)3(2.97 mg, 1 mol%), DavePhos (3.83 mg, 3 mol%) and NaOtBu (43.8 mg, 0.456 mmol) were dissolved in anhydroustoluene (3 mL). 8-Chloroimidazo[1,2-a]pyrazine (49.8 mg, 0.324 mmol) and N-(4-aminophenyl)-4-methylbenzenesulfonamide23 (106 mg, 0.389 mmol) were addedand the reaction was stirred under reflux, under Ar for 16 h. The reaction was cooled to RT and solventremoved in vacuo, before the residuewas taken up in CH2Cl2 (50 mL) and washed with H2O(3 x 30 mL) and brine (30 mL), dried (MgSO4), filtered andconcentrated in vacuo. Flash chromatography (applied in pet. ether;eluted 2:1 pet. ether/EtOAc) afforded the title compound as a brown solid (69.7mg, 0.184 mmol, 56%). Mpt: Decomposed before melting; Rf = 0.30 (3:1 EtOAc/pet. ether); IR (numax/cm-1,thin film): 3338, 3045, 1537, 1505; 1H NMR (600 MHz, CDCl3):deltaH = 2.37 (s, 3H, 21-H),6.88 (s, 1H, 15-H), 7.06 (d, J = 8.8 Hz, 2H, 13-H), 7.21 (d, J = 8.3Hz, 2H, 19-H), 7.45 (d, J = 4.6 Hz, 1H, 6-H), 7.56-7.57 (m, 3H, 2,3,5-H),7.63 (d, J = 8.3 Hz, 2H, 18-H), 7.76 (d, J = 8.8 Hz, 2H, 12-H),8.19 (s, 1H, 10-H); 13CNMR (150 MHz, CDCl3): deltaC = 21.7 (C-21), 111.9 (C-5),115.2 (C-3), 120.3 (C-12), 123.9 (C-13), 127.4 (C-18),128.4 (C-6), 129.7 (C-19), 131.1 (C-14), 131.9 (C-2),133.2 (C-9), 136.2 (C-17), 137.4 (C-11), 143.9 (C-20),146.0 (C-8); LRMS m/z (ES+):380 [M+H]+, 402 [M+Na]+; HRMS m/z (ES+): Found380.1168 [M+H]+; C19H18N5O2Srequires 380.1181.

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:
Article; Sayer, James R.; Walldn, Karin; Pesnot, Thomas; Campbell, Frederick; Gane, Paul J.; Simone, Michela; Koss, Hans; Buelens, Floris; Boyle, Timothy P.; Selwood, David L.; Waksman, Gabriel; Tabor, Alethea B.; Bioorganic and Medicinal Chemistry; vol. 22; 22; (2014); p. 6459 – 6470;,
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 69214-33-1 as follows. Formula: C6H4ClN3

Morpholine (2.0 ml, 23.2 mmol) was added to a stirred solution of a mixture 72/28 of 3-bromo-8-chloro-imidazo[l,2-a]pyrazine and 3,8-dibromo-imidazo[l,2-a]pyrazine (intermediate 15) (5.9 g, 11.6 mmol) and DIPEA (1.93 ml, 13.9 mmol) in ACN (54 ml). The mixture was stirred at 80 C for 7 h. and then the solvent was evaporated in vacuo. The crude product was dissolved in DCM and washed with a saturated solution of sodium carbonate. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 10/90). The desired fractions were collected and evaporated in vacuo and the crude product precipitated from Et20 to yield intermediate 26 (2.79 g, 85%) as a white solid.

According to the analysis of related databases, 69214-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; PASTOR-FERNANDEZ, Joaquin; VAN GOOL, Michiel, Luc, Maria; MARTIN-MARTIN, Maria, Luz; VANHOOF, Greta, Constantia, Peter; WO2011/110545; (2011); 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. 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 69214-33-1

A solution of 8chioroimidazo[i,2a1pyrazine (730 mg, 4.8 mrnol) and NCS (955 mg, 7,2mrnol) in MeCN/DCE (10 rnL/5 rnL ) was heated to 90 C overnight. After LCMS indicated thatstarting material disappeared, the mixture was poured into water (20 mL) and extracted with DCM (20 mL x 3). The combined organic layer was washed with water (20 rnL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo, The residue was purified by chromatography on silica (3% FtOAc in petroleum ether) to give the title compound(700 mg) as a yellow solid. LRMS miz (M+H) 188.1, 190.1 found, 188.1, 190.1 required.

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 69214-33-1.

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