Category: 297172-19-1

Synthetic Route of 297172-19-1, These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-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.

5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine (1.0 g, 7.71 mmol) was dissolved in absolute ethanol (50 mL) and the solution was placed under a nitrogen atmosphere. Cyclohexanecarbaldehyde (1.86 mL, 15.4 mmol) was added and the reaction mixture was stirred 2 h at room temperature. Then it was cooled in an ice-bath and sodium triacetoxyhydroborate (6.54 g, 30.9 mmol) was added portionwise. Stirring was continued at room temperature overnight, after which the reaction mixture was concentrated and partitioned between dichloromethane and water. After separation of the layers, the aqueous layer was basified to pH -14. and it was extracted with dichioromethane three times. The combined extracts were dried over sodium sulfate, filtered and concentrated. Flash chromatography (gradient of methanol in dichloromethane) gave the title compound as a light yellow solid (1 .82 g).1H NMR (ODd3) 6 7.51 (s, 1 H), 6.78 (s, 1 H), 4.05 (t, J = 5.5 Hz, 2H), 3.61 (s, 2H),2.79 (t, J = 5.5 Hz, 2H), 2.32 (d, J = 7.2 Hz, 2H), 1.85 – 1.62 (m, 5H), 1.60 – 1.46 (m, 1H), 1.32-1.10 (m, 3H), 0.98-0.82 (m, 2H).LC/MS m/z 220 [M+H].

The synthetic route of 297172-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ-FERNANDEZ, Jose Luis; ALMANSA-ROSALES, Carmen; NIECZYPOR, Piotr; WO2015/91795; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-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 297172-19-1, Computed Properties of C6H9N3

EXAMPLE 3 5-[5,6-Dihydroimidazo[1,5-a]pyrazin-7(8H)-yl]-3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazoline Prepared from 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine as described for Example 1, step c (0.033 g, 37%). deltaH (360 MHz; CDCl3) 4.07 (2H, dd, J=6 and 6), 4.44 (2H, dd, J=6 and 6), 4.92 (2H, s), 6.93 (1H, s), 7.22-7.32 (2H, m), 7.37-7.41 (1H, m), 7.60 (1H, s), 7.69 (1H, dd, J=8 and 8), 7.96 (1H, dd, J=8 and 8), 8.05-8.09 (2H, m), 8.73 (1H, d, J=8); m/z (ES+) 386 (M+H+).

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

Reference:
Patent; Chambers, Mark Stuart; Collins, Ian James; Goodacre, Simon Charles; Hallett, David James; Jones, Philip; Keown, Linda Elizabeth; Maxey, Robert James; Street, Leslie Joseph; US2003/45532; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-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 94 N-(5-(5,6-dihydroimidazo[1,5-a]pyrazin-7(8H)-yl)pentyl)-5-(thiophen-2-yl)isoxazole-3-carboxamide To a solution of intermediate B (150 mg, 0.54 mmol, 1.0 eq) in CH2ClCH2Cl (10 mL) were added imidazo[1,5-a]pyrazine,5,6,7,8-tetrahydro-(9Cl) (132.7 g, 1.07 mmol, 2.0 eq), NaBH(OAc)3 (685.3 mg, 3.24 mmol, 6.0 eq), acetic acid (97.1 mg, 1.62 mmol, 3.0 eq). Then the mixture was stirred at 15 C. for 12 hours. The mixture was quenched with water (10 mL). The mixture was extracted with DCM. The combined organic phase was concentrated to obtain the crude product which was purified by preparative HPLC (column: Xtimate C18 150*25 mm*5 um, gradient: 33-63% B (A=0.05% ammonia hydroxide/water, B=acetonitrile) to give the title compound (95 mg, 45.7% yield) as a light yellow solid. MS (ESI) m/z 386.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.80 (t, J=5.6 Hz, 1H), 7.86 (dd, J=5.2, 0.8 Hz, 1H), 7.78 (dd, J=4.0, 1.2 Hz, 1H), 7.49 (s, 1H), 7.27-7.25 (m, 1H), 7.16 (s, 1H), 6.61 (s, 1H), 3.97 (t, J=5.6 Hz, 2H), 3.53 (s, 2H), 3.28-3.23 (m, 2H), 2.73 (t, J=5.6 Hz, 2H), 2.45 (t, J=6.8 Hz, 2H), 1.58-1.48 (m, 4H), 1.36-1.30 (m, 2H).

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

Reference:
Patent; NOVARTIS AG; BECKWITH, Rohan Eric John; JIANG, Hua; WANG, Ce; (54 pag.)US2018/271837; (2018); 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 297172-19-1 as follows. Formula: C6H9N3

A flask was charged with tert-butyl (R)-3-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-iodo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5- yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate and tert-butyl (R)-3-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-iodo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5- yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate (REFERENCE EXAMPLE 5) (0.15 g, 0.156 mmol), 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine (0.038 g, 0.313 mmol), Cs2CO3 (0.153 g, 0.469 mmol) and Pd(dppf)Cl2 (0.023 g, 0.031 mmol). The vial was sealed, degassed with N2, and filled with DME (1.56 mL). The resulting mixture was heated overnight at 80 C. The reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated and the residue purified by silica gel column chromatography using (gradient 0-10%) MeOH in DCM as the mobile phase to afford the title compound. LC/MS [M+H]+: 955.82.

According to the analysis of related databases, 297172-19-1, the application of this compound in the production field has become more and more popular.

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

Some common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-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. Product Details of 297172-19-1

To a solution of 2-bromo-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5- carboxamide (0.40 g, 0.98 mmol) and 5,6,7,8-tetrahydroimidazo[1 ,5-a]pyrazine (0.18 g, 1.48 mmol) in dioxane (16 ml_), Cs2C03 (0.96 g, 2.96 mmol) and RuPhos (0.09 g, 0.19 mmol) were added and the reaction mixture was purged with argon for 30 min. Pd2(dba)3 (0.09 g, 0.09 mmol) was added and the reaction mixture was heated in sealed tube at 1 10C for 16h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with H20 (100 ml.) and extracted with EtOAc (3 * 100 ml_). The organic layer was separated, washed with brine (100 ml_), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 100-200 mesh, 0 to 5% MeOH in DCM) and by preparative HPLC to afford 2-(6,8-dihydro-5H-imidazo[1 ,5- a]pyrazin-7-yl)-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5-carboxamide (0.07 g, 14%) as a white solid. HPLC Purity: 98.3% MS (ESI) m/e [M+H]7Rt/%: 449.00/2.76/96.0% 1H NMR (400 MHz, DMSO-d6) delta 0.81 (t, J=6.60 Hz, 3H) 1.18 – 1.35 (m, 4H) 1.44 – 1.60 (m, 2H) 2.82 – 2.92 (m, 2H) 3.89 (t, J=5.38 Hz, 2H) 4.1 1 (d, J=4.40 Hz, 1 H) 4.19 (t, J=5.38 Hz, 2H) 4.71 (s, 2H) 6.83 (s, 1 H) 6.93 – 6.98 (m, 1 H) 7.04 (t, J=7.34 Hz, 1 H) 7.10 (d, J=1.47 Hz, 1 H) 7.31 (d, J=7.82 Hz, 1 H) 7.57 (d, J=7.82 Hz, 1 H) 7.65 (s, 1 H) 7.87 (s, 1 H) 8.01 (d, J=8.80 Hz, 1 H) 10.76 (brs, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 297172-19-1, its application will become more common.

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 297172-19-1, These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-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.

In 0 C lower, to the 5, 6, 7, 8-tetrahydro-imidazo [1, 5-a] pyrazine (50.0 mg, 0 . 40mmol) and Boc-(R)-3-amino-4-(2, 5-difluorophenyl) butanoic acid (128.0 mg, 0 . 40mmol) in dichloromethane (5 ml) is added in solution HOBT (54.5 mg, 0 . 42mmol). The reaction in the 0 C lower stirring 10 min, then adding EDC (96.6 mg, 0 . 50mmol). After removing the ice bath, the reaction stirring at ambient temperature 14h. The mixture is concentrated and used for purifying HPLC (Gilson; YMC-PackProC18 column, 100x20mmI. D. ; A solvent gradient from 10% acetonitrile, 90% water and 0.1% trifluoroacetic acid to 90% acetonitrile, 10% water and 0.1% trifluoroacetic acid), to obtain 103 mg in the form of a solid as the title compound.

Statistics shows that 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 297172-19-1.

Reference:
Patent; CGene Tech (Suzhou,China)Co.,Ltd; YU, QIANG; WEI, FENGPING; (31 pag.)CN101899047; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-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 297172-19-1, SDS of cas: 297172-19-1

General procedure: All reactions were carried out in vials under nitrogen atmosphere. Step 1: A solution of compound 8 (100 mumol, 1.0 equiv) and compound 9 (150 mumol, 1.5 equiv) in DMF (0.1 M) was treated with K2CO3 (300 mumol, 3.0 equiv) and stirred at 110 C for 16 h (LCMS check). The reaction was filtered and the filtrate concentrated to afford 10. The crude aldehyde 10 (100 mumol, 1.0 equiv) was dissolved in acetone:water (2:1, 0.1 M) and treated with KMnO4 (600 mumol, 6 equiv) and stirred at 30 C for 16 h (LCMS check). The reaction was filtered and the filtrate concentrated to afford 11. The crude acid 11 (100 mumol, 1.0 equiv) was treated with HATU (120 mumol, 1.20 equiv) followed by the crude amine (100 mumol, 1.0 equiv) and NEt3 (300 mumol, 3.0 equiv). The reaction was stirred at 30 C for 16 h (LCMS check). The reactions were concentrated and purified directly by reversed phase preparative HPLC using a C18 column and eluting with acetonitrile-water (0.225% formic acid or pH = 10 NH4OH) gradient. All compounds were deemed greater than 95% purity by LCMS and HPLC.

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[1,5-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Londregan, Allyn T.; Piotrowski, David W.; Futatsugi, Kentaro; Warmus, Joseph S.; Boehm, Markus; Carpino, Philip A.; Chin, Janice E.; Janssen, Ann M.; Roush, Nicole S.; Buxton, Joanne; Hinchey, Terri; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1407 – 1411;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem