Imidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro- (9CI) Chemical Properties

Boiling point:

340.0±30.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

8.26±0.20(Predicted)

form 

solid

color 

Cream

CAS DataBase Reference

297172-19-1

Safety Information

HS Code 

2933299090

Imidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro- (9CI) Usage And Synthesis

Uses

5,6,7,8-Tetrahydroimidazo[1,5-A]pyrazine can be used as KRAS G12C inhibitors as antitumor agents.

Synthesis

GENERAL STEPS: 7-Benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine (4.89 g, 22.9 mmol) was dissolved in anhydrous ethanol (200 mL) and 10% palladium carbon catalyst (4.88 g) was added. The reaction mixture was placed under 1 bar hydrogen atmosphere and the reaction was vigorously stirred at room temperature overnight. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filter cake was washed with ethanol. The filtrates were combined, concentrated under reduced pressure and subsequently co-evaporated with dichloromethane to completely remove the residual solvent to afford the target compound 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine as an off-white oil (2.52 g). The product was characterized by 1H NMR (CD3OD): δ 7.42 (s, 1H), 6.77 (s, 1H), 4.07 (s, 2H), 3.99 (t, J = 5.6 Hz, 2H), 3.22 (t, J = 5.6 Hz, 2H), 1.76 (br s, 1H). LC/MS analysis showed m/z 124 [M + H]+, which is consistent with target molecular weight.

References

[1] Patent: WO2015/91795, 2015, A1. Location in patent: Paragraph 36

Imidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro- (9CI)(297172-19-1)Related Product Information

• Azithromycin
• CEFTRIAXONE
• Sulfachoropyrazine sodium
• Imidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro- (9CI)
• 7-(6-Chloro-pyrimidin-4-yl)-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine
• 5,6,7,8-TETRAHYDROIMIDAZO[1,5-A]PYRAZINE DIHYDROCHLORIDE
• 7-(2-chloropyrimidin-4-yl)-3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine
• 7-(2-chloropyrimidin-4-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine
• Imidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro-3-methyl- (9CI)
• 7-(6-Chloro-pyrimidin-4-yl)-3-methyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine
• 3-Bromo-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine
• 3-(2,4-DIFLUOROPHENYL)-5,6,7,8-TETRAHYDROIMIDAZO[1,5-A]PYRAZINE
• ETHYL 5,6,7,8-TETRAHYDROIMIDAZO[1,2-A]PYRAZINE-2-CARBOXYLATE