3-Amino-1H-pyrazole-4-carboxamide Chemical Properties

Melting point:

187-189 °C(Solv: water (7732-18-5))

Boiling point:

454.3±25.0 °C(Predicted)

Density 

1.538±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

DMSO (Slightly), Methanol (Very Slightly)

form 

Solid

pka

13.26±0.50(Predicted)

color 

Off-White to Pale Beige

Safety Information

HS Code 

2933199090

3-Amino-1H-pyrazole-4-carboxamide Usage And Synthesis

Uses

5-Amino-4-pyrazolecarboxamide is used in the synthesis of 4H-3,1-Benzothiazinone analogs as antiproliferative agents against human cancer cell lines. Also, it is an intermediate used in the synthesis of 3-(4H-1,2,4-Triazol-4-yl)-1H-pyrazole-4-carboxamide (T767570), which is an impurity of Allopurinol (A547300), which is a xanthine oxidase inhibitor; decreases uric acid production. Used in treatment of hyperuricemia and chronic gout. Antiurolithic.

Synthesis

General procedure for the synthesis of 3-aminopyrazole-4-carboxamide from 3-amino-4-cyanopyrazole: 5-amino-1H-pyrazole-4-carbonitrile (1) (5 g, 0.046 mol) was slowly added to pre-cooled concentrated sulfuric acid (10 ml) under stirring conditions, and the temperature of the reaction was controlled not to exceed 20 °C. After the addition was completed, the reaction mixture was stirred continuously at room temperature for 4 hours. Subsequently, the reaction solution was slowly poured into ice water under stirring and the mixture was allowed to stand in a refrigerator overnight. The precipitated solid product was collected by filtration and washed with water to remove residual sulfuric acid, which ultimately yielded the target compound 5-amino-1H-pyrazole-4-carboxamide (2) as a white solid with a yield of 5.19 g in 89% yield; melting point 220-222 °C (literature value 222-225 °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] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1191 - 1196

3-Amino-1H-pyrazole-4-carboxamide(5334-31-6)Related Product Information

• p-Aminobenzamide
• Benzamide
• Glycine
• Formamide
• 3-Aminophenol
• ALTRENOGEST
• Chlorantraniliprole
• Pyrazole
• N,N-Dimethylformamide
• 6-Aminocaproic acid
• Tris(hydroxymethyl)aminomethane
• Oxipurinol
• 5-AMINO-1-PHENYLPYRAZOLE-4-CARBOXAMIDE
• 4-HYDROXY-1-PHENYLPYRAZOLO[3,4-D]PYRIMIDINE
• 3-Amino-4-pyrazolecarboxamide hemisulfate
• 5-Amino-1-methylpyrazole-4-carboxamide
• 3-Aminopyrazole
• CARBOXAMIDE