247583-72-8

Basic information

• Product Name: 1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide
• Synonyms: 1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide
• CAS NO: 247583-72-8
• Molecular Formula: C₈H₁₂N₄O₃
• Molecular Weight: 212.20588
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 247583-72-8.mol

Chemical Properties

• Boiling Point: 334.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• Solubility: Dichloromethane, Dimethyl Sulfoxide, Methanol
• PKA: 14.92±0.50(Predicted)
• CAS DataBase Reference: 1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide(247583-72-8)
• EPA Substance Registry System: 1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide(247583-72-8)

Safety Data

• Hazardous Substances Data: 247583-72-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide is used as an intermediate in the preparation of Iso Viagra, a medication designed to treat erectile dysfunction. Its role in the synthesis process is vital for producing an effective treatment option for patients suffering from sexual dysfunction.
Additionally, this compound is utilized as an intermediate in the synthesis of pyrazolopyrimidinone cGMP PDE5 inhibitors. These inhibitors are also employed in the treatment of sexual dysfunction, specifically targeting the enhancement of blood flow to improve erectile function. The use of 1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide in this context highlights its importance in developing therapeutic agents for various sexual health issues.

Upstream product

• 247583-71-7 1-methyl-4-nitro-5-propyl-3-pyrazolecarboxylic acid 
• 36983-31-0 ethyl 3-butyrylpyruvate 
• 247583-70-6 1-methyl-5-propyl-1H-pyrazole-3-carboxylic acid 

Downstream Products

• 247583-78-4 4-Amino-1-methyl-5-propyl-3-pyrazolecarboxamide 
• 501120-38-3 4-(2-ethoxybenzoyl)amino-1-methyl-5-propyl-3-pyrazolecarboxamide 
• 501120-42-9 5-(5-chlorosulfonyl-2-ethoxyphenyl)-2-methyl-3-propyl-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-7-one 
• 501120-40-7 5-(2-ethoxyphenyl)-2-methyl-3-propyl-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-7-one 

Relevant articles and documents

Synthesis and properties of isoviagra [1]. A 2-methyl-2H-pyrazolo[4,3-d]pyrimidin-7-one isomer of Viagra

The synthesis and spectral properties (ir, ms, nmr) of a substituted 2-methyl-2H-pyrazolo[4,3-d]-pyrimidin-7-one (3), an isomer of Viagra, are described. The key synthon, 4-amino-1-methyl-5-propyl-3-pyrazolecarboxamide (7), is prepared via the reaction of ethyl 2,4-dioxoheptanoate with methylhydrazine, followed by cyclization, nitration, amidation, and nitro group reduction. Interaction of 7 with 2-ethoxybenzoyl chloride yielded the respective bis-amide (8) which was cyclized in polyphosphoric acid to the corresponding pyrazolo[4,3-d]pyrimidin-7-one derivative 9. Chlorosulfonylation of 9, and subsequent treatment with 1-methylpiperazine furnished isoViagra (3).

Pyrazolopyrimidinone cGMP PDE5 inhibitors for the treatment of sexual dysfunction

Compounds of the formulae (IA) and (IB): wherein R1is C1to C3alkyl optionally substituted with phenyl, Het or a N-linked heterocyclic group selected from piperidinyl and morpholinyl; wherein said phenyl group is optionally substituted by one or more substitutents selected from C1to C4alkoxy; halo; CN; CF3; OCF3or C1to C4alkyl wherein said C1to C4alkyl group is optionally substituted by C1to C4haloalkyl or haloalkoxy either of which is substituted by one or more halo atoms; R2is C1to C6alkyl and R13is OR3or NR5R6, or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity are potent and selective inhibitors of type 5 cyclic guanosine 3′,5′-monophosphate phosphodiesterase (cGMP PDE5) and have utility in the treatment of, inter alia, male erectile dysfunction (MED) and female sexual dysfunction (FSD).