Category: 91476-80-1

These common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[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. Computed Properties of C6H9N3

Example 97 A mixture of 2-chloro-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (prepared in Example 95) 285 mg, 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 197 mg, triethylamine 0.22 ml and chloroform 3 ml is stirred at room temperature for 2.5 hours, followed by stirring at 60 C. for 2.5 hours. The mixture is diluted with ethyl acetate, and washed with water. The water layer is extracted with ethyl acetate, and the organic layer is washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is purified with silica gel chromatography (silica gel 10 g, solvent; chloroform_methanol=50:1) and concentrated in vacuo and triturated with isopropyl ether to give 2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine as a colorless crystalline powder, 290 mg. mp 179-182 C., MS(m/z): 443(M+H)+

The synthetic route of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yamada, Koichiro; Matsuki, Kenji; Omori, Kenji; Kikkawa, Kohei; US2004/142930; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 91476-80-1, These common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[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.

(1855) [00533] To a solution of 2-(4-bromophenethyl)isoindoline-l,3-dione (prepared according to the procedure described in Francis et al : Journal of Medicinal Chemistry (1991), 34(8), 2570- 2579; 0.2 M in anhydrous 1,4-dioxane; 150 muEpsilon, 30 mumol), was added 5,6,7,8- tetrah droimidazo[ 1 ,2- Jpyrazine (0,2 M in anhydrous 1 ,4-dioxane; 180 muTau, 36 muetaiotaomicron), RuPhos solution (0.02 M in anhydrous 1,4-dioxane/EtOAc; 75 uL, 1.5 mumo), RuPhos-Pd 2nd generation catalyst (0,02 M in anhydrous 1,4-dioxane, 75 mu., 1 ,5 muetaiotaomicron) and sodium fert-butoxide (2 M in THF; 150 mu^, 300 muthetaIota). The resulting mixture was heated at 100 C overnight. The reaction mixture was cooled to RT and used directly in Step 2 without further workup or i solation.

Statistics shows that 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 91476-80-1.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 91476-80-1,Some common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, molecular formula is C6H9N3, 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 2 5-[5,6-Dihydroimidazo[1,2-a]pyrazin-7(8H)-yl]-3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazoline Prepared from 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine as described for Example 1, step c (0.020 g, 23%). deltaH (360 MHz; CDCl3) 4.12 (2H, dd, J=6 and 6), 4.41 (2H, dd, J=6 and 6), 5.02 (2H, s), 6.93 (1H, s), 7.07 (1H, s), 7.21-7.32 (2H, m), 7.36-7.40 (1H, m), 7.68 (1H, dd, J=7 and 7), 7.95 (1H, dd, J=7 and 7), 8.07-8.10 (2H, m), 8.73 (1H, d, J=8); m/z (ES+) 386 (M+H+).

The synthetic route of 91476-80-1 has been constantly updated, and we look forward to future research findings.

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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., name: 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine

Step A: To a solution of NaH (60% dispersion in mineral oil, 0.130 g, 3.25 mmol) in THF (10 mL) was added 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (0.33 g, 2.71 mmol) and the reaction mixture stirred for 10 min. Methyl 2-chlorobenzoxazole-4-carboxylate (478 mg, 2.26 mmol), in THF (10 mL) was added and the reaction mixture was allowed to stir at room temperature 17 h. The reaction mixture was quenched with CH3OH (3 mL), and adsorbed onto silica gel (2 g). The crude product was purified by column chromatography (silica gel, 0.5 to 10% CH3OH in CH2Cl2) to afford methyl 2-(5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)benzoxazole-4-carboxylate (251 mg, 37%) as an orange oil. 1H NMR and MS consistent.

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 91476-80-1.

Reference:
Patent; AMR TECHNOLOGY, INC.; US2008/255114; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 91476-80-1, 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

5,6,7,8-Tetrahydroimidazo[1 ,2-a]pyrazine (0.099 g, 0.804 mmol) was suspended in dichloromethane (DCM) (8 ml). Triethylamine (0.123 ml_, 0.884 mmol) and 2-chloro- 3-(trifluoromethyl)benzoyl chloride (0.195 g, 0.804 mmol) were added and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated in vacuo, the residue dissolved in 1 :1 DMSO/MeOH and purified by mass-directed automated preparative HPLC. Product fractions were concentrated in vacuo to yield an orange gum. This was partitioned between DCM (10ml) and saturated aqueous sodium bicarbonate (4ml) and the organic layer separated. This was concentrated in vacuo to yield 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}- 5,6,7,8-tetrahydroimidazo[1 ,2-a]pyrazine (0.131 g, 0.397 mmol, 49.4 % yield) as a yellow gum. LC/MS [M+H]+ = 330, retention time = 1.02 minutes (5 minute method).

The chemical industry reduces the impact on the environment during synthesis 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine

Production Example 6 1-(2-Hydroxyethyl)-6,8-difluoro-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (compound No. 10) Using 1-(2-hydroxyethyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, the same procedure as in Production Example 1 was followed to yield the title compound. Melting point: 253-255 C. Elemental analysis (for C18 H16 F2 N4 O4.1/2H2 O)

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; Takeda Chemical Industries, Ltd.; US5519024; (1996); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 91476-80-1, These common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[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.

C-1 a (50 mg; 0.16 mmol) is dissolved in dioxane. 5,6,7,8-tetrahydro-imidazo[1 ,2- a]pyrazine E-1a (19 mg; 0.16 mmol), sodium ie f-butoxide (40 mg; 0.42 mmol) and chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1 ,1 ‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-i-butyl ether adduct (9 mg; 0.01 mmol) are added and the reaction mixture is stirred at 75 C for 2 h. The solvents are evaporated under reduced pressure and the crude material is purified using reversed phase chromatography (method: prep. HPLC1 ) to afford I-029. Yield: 48 % (27 mg; 0.08 mmol) HPLC-MS: (M+H)+ = 362; tRet = 0.96 min; method LCMSBAS1

The synthetic route of 91476-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; ARNHOF, Heribert; CAROTTA, Sebastian; HOFMANN, Marco; KERENYI, Marc; SCHARN, Dirk; (118 pag.)WO2019/68613; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[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. Application In Synthesis of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine

Production Example 3 6,7-Difluoro-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-1-(thiazol-2-yl)methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (compound No. 51) A mixture of 0.34 g of 1-(thiazol-2-yl)methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.5 g of 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine and 2 ml of N-methylpyrrolidone was stirred at 60 to 70 C. for 2 hours. After the reaction mixture was concentrated under reduced pressure, 10 ml of water was added to the residue, followed by extraction with chloroform (20 ml *3). After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was recrystallized from ethyl ether to yield 0.06 g of the title compound. Melting point: 210-213 C. Elemental analysis (for C20 H15 F2 N5 O3 S.1/2H2 O)

The synthetic route of 91476-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5519024; (1996); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 91476-80-1, 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 150 mg (0.28 mmol) of 2-[(3R)-3-methylmorpholin-4-yl]-8-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]-1,7-naphthyridin-4-yl trifluoromethanesulfonate and 119 mg (0.97 mmol) 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine in 0.42 ml of MeCN was stirred at 70C for 48 h under argon. After cooling the reaction mixture was diluted with ethyl acetate and THE and washed with saturated aqueous sodium chloride solution. The organic phase was filtered using a Whatmanfilter and then concentrated to give the crude product that was used without further purification in the next step.

The chemical industry reduces the impact on the environment during synthesis 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WORTMANN, Lars; LUeCKING, Ulrich; LEFRANC, Julien; BRIEM, Hans; KOPPITZ, Marcus; EIS, Knut; VON NUSSBAUM, Franz; BADER, Benjamin; WENGNER, Antje Margret; SIEMEISTER, Gerhard; BONE, Wilhelm; LIENAU, Philip; GRUDZINSKA-GOEBEL, Joanna; MOOSMAYER, Dieter; EBERSPAeCHER, Uwe; SCHICK, Hans; (509 pag.)WO2016/20320; (2016); 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine

Example 32 (5,6-Dihydro-8H-imidazo[1,2-a]pyrazin-7-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone A mixture of sodium 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylate (0.3 g) and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine (0.24 g). HBTu (0.4 g), DIEA (1 mL), THF (3 mL) and DMA (3 mL) was stirred at room temperature for three hours. The reaction mixture was then partitioned between EtOAc and water, the organic layer washed with saturated NaHCO3 and water, dried over Na2SO4 and concentrated in vacuo. The residue was purified via prep. TLC (10% MeOH/DCM) to give 56 mg of (5,6-dihydro-8H-imidazo[1,2-a]pyrazin-7-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone. MS (M+H)=578.

According to the analysis of related databases, 91476-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gong, Leyi; Tan, Yun-Chou; US2011/301170; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem