3-HYDROXYPYRAZINE-2-CARBOXAMIDE Chemical Properties

Melting point:

ca 270℃

Density 

1.63±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Aqueous Base (Slightly)

form 

Solid

pka

10.69±0.40(Predicted)

color 

Pale Brown to Brown

λmax

348nm(lit.)

Stability:

Hygroscopic

InChI

InChI=1S/C5H5N3O2/c6-4(9)3-5(10)8-2-1-7-3/h1-2H,(H2,6,9)(H,8,10)

InChIKey

SZPBAPFUXAADQV-UHFFFAOYSA-N

SMILES

C1(C(N)=O)=NC=CNC1=O

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37

HS Code 

29339900

3-HYDROXYPYRAZINE-2-CARBOXAMIDE Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

Apart from biological importance of pyridine-2-carboxamide (picolinamide, pia) as well as of its derivatives such as 3-hydroxypyridine-2-carboxamide (3-OHpia), as ligands they have found their extensive application in coordina- tion chemistry in crystal engineering .

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 78, 1949 DOI: 10.1021/ja01169a023

Synthesis

The general procedure for the synthesis of 3-hydroxypyrazine-2-carboxamide from the compound (CAS:131543-46-9) and 2-aminomalonamide was carried out as follows: firstly, diethylaminomalonate (in the form of hydrochloric acid) was dissolved in water, and pH was adjusted by adding sodium bicarbonate to a value greater than 7. Subsequently, an extraction operation was carried out, and the organic phase was evaporated under reduced pressure. The product obtained was quantitatively converted to aminodicarbonamide by treating the product with an aqueous ammonia solution at 80 °C overnight. The product obtained in this step does not require further purification and can be directly dissolved in water for the next reaction. Next, glyoxal sodium bisulfite hemihydrate was added to this aqueous solution and the reaction mixture was stirred at 90°C for 3 hours. After completion of the reaction, the reaction mixture was adjusted to alkaline with 58% NH4OH solution. A 30% H2O2 solution was added dropwise to the rapidly stirred cold solution at 0°C. The reaction mixture was allowed to stand at room temperature to induce precipitation of 2-hydroxy-3-carboxamide pyrazine. Finally, the solid product was collected in 63% yield and purified by partial recrystallization. References: [J. Med. Chem. 1983, 26, 283-86], [J. Heterocyclic Chem. 1979, 16, 193].

References

[1] Patent: WO2007/144686, 2007, A1. Location in patent: Page/Page column 129-130
[2] Patent: JP5739618, 2015, B2. Location in patent: Paragraph 0024
[3] Patent: US2018/141920, 2018, A1. Location in patent: Paragraph 0215; 0216; 0217; 0218; 0219; 0220; 0221; 0222

3-HYDROXYPYRAZINE-2-CARBOXAMIDE(55321-99-8)Related Product Information

• Methyl 6-bromo-3-oxo-3,4-dihydropyrazine-2-carboxylate
• 6-Bromo-3-chloropyrazine-2-carbonitrile
• 3-Chloropyrazine-2-carbonitrile
• Pyrazinecarboxamide, 3,6-difluoro- (9CI)
• 3-OXO-3,4-DIHYDROPYRAZINE-2-CARBONITRILE
• 2-Pyrazinecarbonitrile, 6-fluoro-3,4-dihydro-3-oxo-, coMpd. with N-cyclohexylcyclohexanaMine (1:1)
• 2-HYDROXYPYRAZINE
• 2-Pyrazinecarbonitrile, 3-fluoro-
• Cefepime
• 3,6-DibroMopyrazine-2-carbonitrile
• Pyrazinecarboxamide, 6-fluoro- (9CI)
• Pyrazinecarboxamide, 5-fluoro-3,4-dihydro-3-oxo- (9CI)
• 3-HYDROXYPYRAZINE-2-CARBOXAMIDE
• (3-METHOXY-PYRAZIN-2-YL)-MORPHOLIN-4-YL-METHANONE
• 5-Hydroxypyrazine-2-carboxamide
• BUTTPARK 91\04-18
• SALOR-INT L101621-1EA
• 3-HYDROXY-5,6-DIPHENYL-2-PYRAZINECARBOXAMIDE