139756-01-7

Basic information

• Product Name: 1-Methyl-4-nitro-3-propyl-(1H)-pyrazole-5-carboxamide
• Synonyms: 1-methyl-4-nitro-3-propyl-(1h)-pyrazole-5-carboxamide;1-Methyl-3-Propyl-4-Nitro-5-Carboxamide Pyrazole;1-Methyl-3-Propyl-4-Nitro-5-Carboxamide-(1H)-Pyrazole;2-methyl-4-nitro-5-propylpyrazole-3-carboxamide;1H-Pyrazole-5-carboxamide,1-methyl-4-nitro-3-propyl-;1-methyl-4-nitro-3-propyl-1H-5-pyrazole carboxamide
• CAS NO: 139756-01-7
• Molecular Formula: C₈H₁₂N₄O₃
• Molecular Weight: 212.20588
• Product Categories: Erectile Dysfunction;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 139756-01-7.mol

Chemical Properties

• Melting Point: 137.0 to 141.0 °C
• Boiling Point: 334.559 °C at 760 mmHg
• Flash Point: 156.136 °C
• Appearance: /
• Density: 1.453 g/cm³
• Vapor Pressure: 0.000127mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 14.62±0.50(Predicted)
• CAS DataBase Reference: 1-Methyl-4-nitro-3-propyl-(1H)-pyrazole-5-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-4-nitro-3-propyl-(1H)-pyrazole-5-carboxamide(139756-01-7)
• EPA Substance Registry System: 1-Methyl-4-nitro-3-propyl-(1H)-pyrazole-5-carboxamide(139756-01-7)

Safety Data

• Hazardous Substances Data: 139756-01-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Methyl-4-nitro-3-propyl-(1H)-pyrazole-5-carboxamide is used as an intermediate in the production of Sildenafil, a medication primarily used to treat erectile dysfunction. Its role in the synthesis process is crucial for the development of this widely prescribed drug, highlighting its importance in the pharmaceutical sector.
Used in Chemical Synthesis:
As a versatile organic compound, 1-Methyl-4-nitro-3-propyl-(1H)-pyrazole-5-carboxamide can be utilized in various chemical synthesis processes. Its unique structure allows it to serve as a building block for the creation of other complex molecules, making it a valuable component in the development of new compounds with potential applications in various industries.
Used in Research and Development:
Due to its unique chemical properties and potential applications, 1-Methyl-4-nitro-3-propyl-(1H)-pyrazole-5-carboxamide is also used in research and development. Scientists and researchers can explore its properties and reactivity to create new compounds or improve existing ones, further expanding its utility in various fields.

InChI:InChI=1/C8H12N4O3/c1-3-4-5-6(12(14)15)7(8(9)13)11(2)10-5/h3-4H2,1-2H3,(H2,9,13)

Upstream product

• 139756-00-6 1-methyl-2-nitro-3-propyl-1H-pyrazole-5-carboxylic acid 
• 360068-47-9 1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carbonyl chloride 
• 36983-31-0 ethyl 3-butyrylpyruvate 
• 92945-27-2 ethyl 3-propyl-1H-pyrazole-5-carboxylate 
• 107-87-9 2-Pentanone 
• 133261-07-1 1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester 
• 139755-99-0 1-methyl-3-propyl-1 H-pyrazole-5-carboxylic acid 

Downstream Products

• 139756-02-8 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 
• 139756-21-1 5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one 
• 139756-03-9 4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 
• 247584-10-7 4-amino-1-methyl-3-n-propylpyrazole-5-carboxamide hydrochloride 
• 200575-15-1 4-[2-ethoxy-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 
• 139756-22-2 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 
• 147676-70-8 5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one 

Relevant articles and documents

A new process for the synthesis of sildenafil intermediate and resulting sildenafil intermediates (by machine translation)

The present invention discloses a new process for the synthesis of sildenafil intermediate and resulting sildenafil intermediate, which belongs to the technical field of pharmaceutical intermediates. The invention comprises the following steps: S1: nitration reaction to 1 - methyl - 3 - propyl pyrazole - 5 - carboxylic acid ethyl ester as the starting material, adopts concentrated sulfuric acid and concentrated nitric acid to the starting material to nitration, shall nitration product; S2: amidation reaction uses ammonium chloride and trimethyl aluminum of the nitration reagent to the aminolysis product aminolysis, quenching, separation, drying, evaporation of the solvent, shall be sildenafil intermediate 1 - methyl - 3 - propyl - 4 - nitryl pyrazole - 5 - carboxamide. The invention from an initial raw material to the target product only needing two-step reaction can be completed, the process flow is short, mild condition, a substantial increase in product yield, save a large number of strong acid, strong alkali and thionyl chloride and other inorganic irritation raw materials, will not cause corrosion of the apparatus, to reduce the large amount of waste water and waste acid, reduce the environmental pressure. (by machine translation)

Sildenafil intermediate 4 - amino -1 - methyl -3 - n-propyl pyrazole -5 - carboxamide green new synthetic process

The invention discloses a new green process of a medicament for treating male erectile dysfunction, namely a sildenafil citrate key intermediate compound 4-amino-1-methyl-3-n-propyl pyrazole-5-formamide. According to the method provided by the process, the safety is high, the reaction is easy to control, less pollution is caused to the environment, and solvent can be recovered and repeatedly used, thereby lowering the cost, reducing the emission, and ensuring that the process is greener and more environment-friendly.

Synthesis method for industrially producing sildenafil amide intermediate

The invention discloses a synthesis method for a sildenafil amide intermediate 1-methyl-3-propyl-4-nitropyrazole-5-formamide, and the synthesis method is easy and convenient to operate and suitable for industrial production. According to the method, harm of thionyl chloride to instruments and equipment is specifically reduced, appropriate solvent is found to protect acyl chloride, and the yield is greatly increased. The method is high in safety, easy and convenient to operate and little in environmental pollution, the used solvent can be recycled, and the industrial cost is greatly reduced.

NOVEL COMPOUNDS FOR USE IN COGNITION IMPROVEMENT

Novel compounds for use in cognition improvement It relates to certain compounds having a polycyclic structure and a -(C=O)NRaRb moiety, wherein the polycyclic structure comprises at least three ring systems, wherein one ring system is a polycyclic ring system comprising from 2 to 4 rings; at least one ring is an aromatic ring; and wherein the structure comprises at least 3 nitrogen atoms and 1 oxygen atom. It also relates to pharmaceutical compositions containing them, and to their use in medicine, in particular in the treatment and/or prevention of neurological disorders coursing with a cognition deficit or impairment, or neurodegenerative diseases.

Novel pyrazole-5-carboxamide and pyrazole-pyrimidine derivatives: Synthesis and anticancer activity

A series of novel pyrazole-5-carboxamide and pyrazole-pyrimidine derivatives were designed and synthesized. All compounds have been screened for their antiproliferative activity against MGC-803, SGC-7901 and Bcap-37 cell lines in vitro. The results revealed that compounds 8a, 8c and 8e exhibited strong inhibitory activity against MGC-803 cell line. The flow cytometric analysis result showed that compound 8e could inhibit MGC-803 proliferation. Some title compounds were tested against telomerase, and compound 8e showed the most potent inhibitory activity with IC50 value at 1.02 ± 0.08 μM. The docking simulation of compound 8e was performed to get the probable binding model, among them, LYS 189, LYS 372, LYS 249 and ASP 254 may be the key residues for the telomerase activity.

PYRAZOLOPYRIMIDINONES FOR THE TREATMENT OF IMPOTENCE AND PROCESS FOR THE PREPARATION THEREOF

The present invention relates to Pyrazolopyrimidinone compounds as PDE5 inhibitors with better IC50 value, good in vivo efficacy and PK profile and a process for the preparation thereof. The present invention covers the pyrazolo pyrimidinone based compounds that have been designed, synthesized and screened for PDE5 inhibitory activity and its PDE5 inhibitory potential is provided in this invention. These designer compounds have shown nanomolar potency when screened for PDE5 inhibitory activity and also shown better in vivo efficacy. These compounds can be used in the treatment of male erectile dysfunction or in the treatment of impotence.

NOVEL COMPOUNDS AS DUAL INHIBITORS OF PHOSPHODIESTERASES AND HISTONE DEACETYLASES

It relates to certain compounds having a polycyclic structure and a hydroxamic acid moiety, wherein the polycyclic structure comprises at least three ring systems, wherein one ring system is a polycyclic ring system comprising from 2 to 4 rings; at least one ring is an aromatic ring; and wherein the structure comprises at least 3 nitrogen atoms and 1 oxygen atom. It also relates to a process for their preparation, as well as to pharmaceutical compositions containing them, and to their use in medicine, in particular in the treatment and/or prevention of neurological disorders coursing with a cognition deficit or impairment, or neurodegenerative diseases. wherein B1 is a radical selected from the group consisting of formula (A"), formula (B"), formula (C"), and formula (D"):

HIGHLY SELECTIVE and LONG-ACTING PDE5 MODULATORS

Disclosed herein are substituted phosphodiesterase type 5 enzyme modulators of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

Comparison of different heterocyclic scaffolds as substrate analog PDE5 inhibitors

Several different heterocyclic systems were compared as PDE5 inhibitor scaffolds. In addition to the known 3H-imidazo[5,1-f][1,2,4]triazin-4-ones and pyrazolopyrimidinones, isomeric imidazo[1,5-a][1,3,5]triazin-4(3H)-ones were also shown to be potent and selective PDE inhibitor scaffolds with in vivo activity. SAR trends were elucidated for sulfonamide derivatives with generality across different scaffolds.

5,7-DIAMINOPYRAZOLO`4,3-D!PYRIMIDINES USEFUL IN THE TREATMENT OF HYPERTENSION

This invention relates to compounds of formula (I).