| Identification | Back Directory | [Name]
3-Amino-1H-pyrazole-4-carboxamide | [CAS]
5334-31-6 | [Synonyms]
Allopurinol EP IMpurity A
3-Amino-4-carbamoylpyrazole
5-Amino-1H-pyrazole-4-car...
3-AMino-1H-pyrazole-4-car...
3-AMINOPYRAZOLE-4-CARBOXAMIDE
5-Amino-4-pyrazolecarboxamide
3-Amino-1H-pyrazole-4-carboxamide
5-azanyl-1H-pyrazole-4-carboxamide
1H-Pyrazole-4-carboxamide, 3-amino-
3-Amino-1H-pyrazole-4-carboxamide 98%
5-Amino-1H-pyrazole-4-carboxylic amide
3-AMino-1H-pyrazole-4-carboxylic aMide
3-AMINO-PYRAZOLE-4-CARBOXYLIC ACID AMIDE
3-Amino-1H-pyrazole-4-carboxylic acid amide
(E)-3-methyl-2-pentenedioic acid dimethyl ester
5-aMino-1H-pyrazole-4-carboxaMide hydrochloride
3-Amino-4-carbamoyl-1H-pyrazole, 3-Amino-4-(aminocarbonyl)-1H-pyrazole | [EINECS(EC#)]
226-252-3 | [Molecular Formula]
C4H6N4O | [MDL Number]
MFCD00082808 | [MOL File]
5334-31-6.mol | [Molecular Weight]
126.12 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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