Category: 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., HPLC of Formula: C6H9N3

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

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. SDS of cas: 91476-80-1

6-chloro-2-(l,l-dimethylethyl)-l,3-benzoxazole-7-sulfonyl chloride (457 mg) was dissolved in 2.5 mL DCM and the solution was cooled to 0 0C. Triethylamine (0.41 mL) was added followed by 5,6,7,8-tetrahydroimidazo[l,2-alpha]pyrazine (201 mg) dissolved in 2.5 mL DCM. The reaction mixture was stirred at 0 0C to room temperature over night. The reaction was quenched with water and extracted with DCM (3×10 mL). The combined organic layers were dried Na2SOzI, filtered and the solvent was removed in vacuo. The crude product was purified by column chromatography eluting with a gradient of 0 to 20% MeOH in DCM yielding 409 mg of product. Rf: 0.57 (10% MeOH in DCM).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 91476-80-1, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/124423; (2007); A2;,
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., COA of Formula: C6H9N3

To a solution of 2-bromo-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5- carboxamide (0.25 g, 0.61 mmol) and 5,6,7,8-tetrahydroimidazo[1 ,2-a]pyrazine (0.09 g, 0.74 mmol) in dioxane (5 ml_), NaOtBu (0.09 g, 0.92 mmol) and RuPhos (0.06 g, 0.12 mmol) were added. The reaction mixture was purged with argon for 20 min followed by addition of Pd2(dba)3 (0.06 g, 0.06 mmol). The reaction mixture was heated at 1 10C for 6h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with H20 (70 mL) and extracted with EtOAc (3 x 100 mL). The organic layer was separated, washed with brine (75 mL), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 230-400 mesh, 0 to 6% MeOH in DCM) and preparative HPLC to afford 2-(6,8-dihydro-5H-imidazo[1 ,2-a]pyrazin-7-yl)-N-[1- (1 H-indol-3-ylmethyl)pentyl]thiazole-5-carboxamide (0.06 g, 19%) as an off- white solid. HPLC Purity: 98.7% MS (ESI) m/e [M+H]+/Rt %: 449.00/2.24/99.2% 1H NMR (400 MHz, DMSO-d6) delta 0.81 (t, J=6.85 Hz, 3H) 1.16 – 1.30 (m, 4H) 1.47 – 1.62 (m, 2H) 2.78-2.94 (m, 2H) 3.92-3.98 (m, 2H) 4.04-4.14 (m, 3H) 4.66 (s, 2H) 6.91 (s, 1 H) 6.95 (d, J=7.34 Hz, 1 H) 7.03 (t, J=7.58 Hz, 1 H) 7.09 (brs, 1 H) 7.14 (s, 1 H) 7.30 (d, J=7.83 Hz, 1 H) 7.56 (d, J=7.83 Hz, 1 H) 7.86 (s, 1 H) 8.01 (d, J=8.31 Hz, 1 H) 10.74 (brs, 1 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; UCB BIOPHARMA SPRL; HALL, Adrian; PROVINS, Laurent; MACCOSS, Malcolm; (72 pag.)WO2018/138088; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products 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.

(6) A mixture of whole amount of 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-methylsulfinylpyrimidine (prepared in the above (5)), 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 73 mg, triethylamine 0.083 ml and N,N-dimethylacetamide 4 ml is stirred at 110 C. for 4 hours. After cooling the reaction mixture is diluted with a 10% aqueous citric acid solution and washed with ethyl acetate. The organic layer is extracted with a 10% aqueous citric acid solution. The water layer is made basic with sodium hydrogen carbonate and extracted with ethyl acetate. The ethyl acetate layer is washed, dried and concentrated in vacuo. The residue is separated with silica gel chromatography (solvent; chloroform_methanol=100:1?50:1), and then crystallized from a mixture of ethyl acetate, methanol and isopropyl ether to give 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine as a colorless crystalline powder 20 mg. mp 179-180 C. IR (Nujol)cm-1: 3380, 3181, 1664, 1572, 1533, 1463 APCI-MS(m/z): 528(M+H)+

The synthetic route of 91476-80-1 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

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. HPLC of Formula: C6H9N3

5,6,7,8-Tetrahydroimidazo[1 ,2-a]pyrazine(l17) (4.53 g, 36.8 mmol) and triethylamine (6.16 mL, 44.2 mmol) were dissolved in dichloromethane (DCM) (200 mL) and treated with di-tert-butyl dicarbonate (10.25 mL, 44.2 mmol). The solution was stirred at RT for 48 h and concentrated in vacuo to afford a crude oil. The crude product was purified by flash chromatography (Isolera, 340 g, 0-100% 2M ammonia in methanokdichloromethane (1 :9)/dichloromethane) to afford 3 fractions. Fraction 2 was identified by LC/MS as containing desired product. The residue was dissolved in ethyl acetate (300 ml), washed with saturated sodium bicarbonate solution (50 ml_), water (2 x 50 ml_), brine (50 ml_), dried over anhydrous sodium sulfate and concentrated to afford product in 6.77g. LC/MS = 224 (M+H)+, retention time = 0.71 minutes (2 minute method (high pH)).

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

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., Product Details of 91476-80-1

A mixture of (2-chloropyrimidin-4-yl)-(l -isopropyl-1 H-imidazo[4,5-c]pyridin-6-yl)amine (Example 12, step 4) (70 mg, 0.24 mmol), 5,6,7,8-tetrahydroimidazo[l,2-a]pyrazine (44 mg, 0.36 mmol), triethylamine (0.15 mL) in isopropyl alcohol (0.5 mL) was heated at 150 C under microwave irradiation on high absorbance for 2.5 h. The cooled reaction mixture was poured onto an SCX cartridge; the cartridge was washed with MeOH followed by elution of the product with 2M NH3 in MeOH. The product containing fractions were concentrated in vacuo and the resulting residue was crystallised from MeOH/EtOAc to afford the title compound as a white solid (55 mg, 62%). LCMS (ESI): RT 1.72 min, [M+H]+ 376.0, Method = E. lH NMR (400 MHz, CDC13): delta 8.75 (1H, d, J = 1.0 Hz), 8.29 (1H, s), 8.06 (1H, d, J = 5.7 Hz), 7.95 (1H, s), 7.66 (1H, s), 7.02 (1H, d, J = 1.3 Hz), 6.86 (1H, d, J = 1.3 Hz), 6.22 (1H, d, J = 5.7 Hz), 5.08 (2H, s), 4.79-4.67 (1H, m), 4.30 (2H, t, J = 5.4 Hz), 4.07 (2H, t, J = 5.4 Hz), 1.70 (6H, d, J = 6.7 Hz).

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; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 91476-80-1, 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. 91476-80-1 name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, 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.

Compound 2A (126.0mg, 0.48mmol) was dissolved in 10.0ml acetonitrile, Ar gas protection. Compound 3a-1 (118.0mg, 0.96mmol), and lithium perchlorate (102.0mg, 0.96mmol), the reaction mixture was heated to 80 deg. C, the reaction after 20 hours, cooled to room temperature.The reaction mixture was evaporated to dryness and the residue with CH2Cl2Dissolved, the organic phase was washed 3 times with saturated NaCl solution, dried over anhydrous Na2SO4Dried, filtered, and evaporated to dryness and the residue was separated by column chromatography (dichloromethane: methanol = 100: 1-50: 1), to give a compound 80.8mg as a white solid, mp: 86-88 deg. C, a yield of 45.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy of Sciences, Shanghai Institute of Medicine; Nanjing Changao Pharmaceutical Technology co., LTD; YANG, YU SHE; CAO, XU FENG; LI, ZHAN; LI, WEI; (78 pag.)CN103965194; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 91476-80-1, 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 547 A solution of (S)-3-(2-((S)-1-(4-(chloromethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (75 mg, 0.2 mmol) and 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (25 mg, 0.2 mmol) in DMSO (2 mL) was heated at 80 C. for 16 h. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL). After separation, the aqueous phase was washed with EtOAc (2*15 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (MeOH in CH2Cl2 0 to 10%) provided (S)-3-(2-((S)-1-(4-((5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (58 mg, white solid) in 62.8% yield. 1H NMR (400 MHz, MeOD) delta 8.12 (d, J=6.0 Hz, 1H), 7.34 (d, J=5.9 Hz, 1H), 7.33 (s, 4H), 6.99 (d, J=1.3 Hz, 1H), 6.89 (d, J=1.4 Hz, 1H), 5.07 (q, J=7.0 Hz, 1H), 4.68 (br s, 1H), 4.37-4.25 (m, 2H), 4.02 (t, J=5.5 Hz, 2H), 3.72 (s, 2H), 3.63 (s, 2H), 2.90 (td, J=5.4, 2.6 Hz, 2H), 1.84 (br s, 1H), 1.51 (d, J=7.0 Hz, 3H), 0.72 (br s, 3H), 0.57 (br s, 3H); HRMS m/z 462.2606 (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, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; Caferro, Thomas Raymond; Cho, Young Shin; Costales, Abran Q.; Lei, Huangshu; Lenoir, Francois; Levell, Julian Roy; Liu, Gang; Palermo, Mark G.; Pfister, Keith Bruce; Sendzik, Martin; Shafer, Cynthia; Shultz, Michael David; Smith, Troy; Sutton, James Clifford; Toure, Bakary-Barry; Yang, Fan; Zhao, Qian; US2014/235620; (2014); 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., Recommanded Product: 91476-80-1

The title compound was prepared from 5,6,7,8-tetrahydroimidazo[1,2-c]pyrazine (31.3 mg, 0.254 mmol, from Step B), (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(3,4-difluorophenyl)butanoic acid (80 mg, mmol), DIPEA (32.8 mg, 0.254 mmol), HOBT (41.2 mg, 0.305 mmol) and EDC (73 mg, 0.381 mmol) in 5 mL of dichloromethane, using a procedure analogous to that described in Example 1, Step C. Purification by HPLC (Gilson; YMC-Pack Pro C18 column, 100×20 mm I.D.; solvent gradient system from 10% acetonitrile, 90% water, and 0.1% trifluoroacetic acid to 90% acetonitrile, 10% water, and 0.1% trifluoroacetic acid) gave 75 mg of the title compound as a viscous oil. 1H NMR (500 MHz, CDCl3) delta 1.38 (s, 9H), 2.05 (bs, 1H), 2.62 (m, 2H), 2.89 (m, 2H) 3.81-4.04 (m, 5H), 4.64-4.88 (m, 2H). 5.38 (m, 1H) 6.88 (m, 2H), 7.05 (m, 3H). ESI-MS 421 (M+1)

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; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 91476-80-1, 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To (3R)-tert-butyl 3-(2-(N,N-bis(4-methoxybenzyl)sulfamoyl)-4-iodo-3-(1-(4- methoxybenzyl)-1H-tetrazol-5-yl)phenylsulfonamido)pyrrolidine-1-carboxylate (REFERENCE EXAMPLE 5) (120 mg, 0.125 mmol) and 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (30.8 mg, 0.250 mmol), Cs2CO3 (122 mg, 0.375 mmol), and RAC-BINAP-Pd-G3 precatalyst (25 mg, 0.025 mmol) were added to DME (2.5 mL) at RT and the mixture was degassed for 10 min under nitrogen, stirred at 80 C overnight. The mixture was diluted with water (50 mL), extracted with EtOAc (2 x 50 mL). The combined organic phases were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a gradient of 0 – 25% heptane/ethanol over 20 min to give the title product. LC/MS [M+H]: 955.

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; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; SCOTT, Jack, D.; TANG, Haiqun; ZHAO, Zhiqiang; YANG, Dexi; XIAO, Li; GU, Xin; JIANG, Jinlong; (85 pag.)WO2019/135920; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem