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53525-65-8

53525-65-8 Structure

53525-65-8 Structure
IdentificationBack Directory
[Name]

5H,10H-DIIMIDAZO[1,5-A:1', 5'-D] PYRAZINE-5,10-DIONE
[CAS]

53525-65-8
[Synonyms]

SPECS AN-584/43226970
DIIMIDAZO[1,5-A:1',5'-D]PYRAZINE-5,10-DIONE
Diimidazo[1,5-a:1’,5’-d)pyrazine-5,10-dione,HCl
DiiMidazo[1,5-a:1',5'-d]pyrazine-5,10-dione, DiHCl
5H,10H-DIIMIDAZO[1,5-A:1', 5'-D] PYRAZINE-5,10-DIONE
5H,10H-DiiMidazo[1,5-a:1', 5'-d] pyrazine-5,10-dione b
5H,10H-Diimidazo[1,5-A:1', 5'-D] pyrazine-5,10-dione ,98%
Diimidazo[1,5-a:1',5'-d]pyrazine-5,10-dione, dihydrochloride
[Molecular Formula]

C8H4N4O2
[MDL Number]

MFCD01631199
[MOL File]

53525-65-8.mol
[Molecular Weight]

188.14
Chemical PropertiesBack Directory
[storage temp. ]

2-8°C
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H312-H332
[Precautionary statements ]

P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501
Hazard InformationBack Directory
[Synthesis]

1H-Imidazole-4-carboxylic acid

1072-84-0

5H,10H-DIIMIDAZO[1,5-A:1', 5'-D] PYRAZINE-5,10-DIONE

53525-65-8

General procedure for the synthesis of imidazo[1,5-a:1',5'-d]pyrazine-5,10-dione from 1H-imidazole-4-carboxylic acid: 1H-imidazole-4-carboxylic acid (5 g, 44.6 mmol) was suspended in thionyl chloride (75 mL), and heated and refluxed under stirring for 18 hours. After completion of the reaction, the reaction mixture was cooled, filtered, washed with toluene and dried under high vacuum to afford the target compound imidazo[1,5-a:1',5'-d]pyrazine-5,10-dione as a yellow solid in 95% yield. Molecular formula: C8H4N4O2, molecular weight: 188.14 g/mol, melting point: 265-268°C. 1H NMR (300 MHz, DMSO-d6) δ: 8.24 (d, 1H, CHC-CO), 8.32 (d, 1H, CHC-CO, J=3Hz), 8.88 (d, 1H, CHN), 9.28 (d, 1H , CHN, J=3Hz).13C NMR (100 MHz, DMSO-d6) δ: 123.99, 124.52, 125.62, 137.26, 139.73, 150.39, 159.68.MS (ESI+, QTof, m/z): 189.0 [M + H]+.

[References]

[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 13, p. 6601 - 6610
[2] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 909 - 919
[3] Pharmaceutical Chemistry Journal, 1986, vol. 20, # 7, p. 460 - 463
[4] Khimiko-Farmatsevticheskii Zhurnal, 1986, vol. 20, # 7, p. 799 - 802
[5] Patent: EP1439169, 2004, A1. Location in patent: Page 81-82
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