Description
The molecular structure of 3-Amino-4-pyrazolecarbonitrile(16617-46-2) contains a cyano structure and an active amino unit. Its solubility in water is low, but its solubility in alcoholic organic solvents is high. As an intermediate in organic synthesis and medicinal chemistry, 3-Amino-4-pyrazolecarbonitrile can synthesize drug molecules. For example, it can be used to synthesize the drug molecule zaleplon.
Chemical Properties
Tan Crystalline Solid
Uses
3-Amino-4-pyrazolecarbonitrile(16617-46-2) has been a useful synthetic intermediate.
Application
3-Amino-4-pyrazolecarbonitrile is a pharmaceutical intermediate ingredient used in the preparation of antineoplastic drugs (Ibrutinib) and hypnotics (Zaleplon).
Pharmaceutical Applications
3-Amino-4-pyrazolecarbonitrile is a key synthetic intermediate of the drug molecule zaleplon, a novel sedative-hypnotic drug with sedative-hypnotic, muscle relaxant, anti-anxiety and anticonvulsant effects.
Synthesis
The general procedure for the synthesis of 3-amino-4-cyanopyrazole from ethoxymethylene malononitrile was as follows: hydrazine hydrate (5 g, 0.156 mol) was slowly added dropwise to an ethanol solution containing 2-(ethoxymethylene)malononitrile (8.64 g, 0.070 mol), and the reaction mixture was subsequently heated for 30 min on a steam bath. A white precipitate gradually precipitated during the reaction and the reaction mixture was transferred to a refrigerator and left overnight to complete crystallization. Subsequently, the white solid product was collected by filtration and washed with a small amount of pre-cooled ethanol to finally obtain the target compound 5-amino-1H-pyrazole-4-carbonitrile (1) as white crystals in 86% (3.05 g) yield; the melting point was 168-170 °C (literature value: 169-170 °C) [33].
References
[1] Bioorganic Chemistry, 2018, vol. 79, p. 46 - 59
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 24 - 35
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1161 - 1166
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 16, p. 4736 - 4741
[5] Patent: CN103626776, 2017, B. Location in patent: Paragraph 0091; 0092; 0093
