200575-15-1

Basic information

• Product Name: 1H-PYRAZOLE-5-CARBOXAMIDE, 4-[[2-ETHOXY-5-[(4-METHYL-1-PIPERAZINYL)SULFONYL]BENZOYL]AMINO]-1-METHYL-3-PROPYL-
• Synonyms: 1H-PYRAZOLE-5-CARBOXAMIDE, 4-[[2-ETHOXY-5-[(4-METHYL-1-PIPERAZINYL)SULFONYL]BENZOYL]AMINO]-1-METHYL-3-PROPYL-;4-[[2-ethoxy-5-[(4-methyl-1-piperazinyl)sulfonyl]benzoyl]amino]-1-methyl-3-propyl-1h-pyrazole-5-carboxamide;4-[2-Ethoxy-5-(4-methyl-1-piperazinylsulfonyl)benzamido]-1-3-propyl-1H-pyrazole-5-carboxamide;4-[2-ETHOXY-5-(4-METHYLPIPERAZINE-1-SULFONYL)BENZAMIDO]-1-METHYL-3-PROPYLPYRAZOLE-5-CARBOXAMIDE;1H-Pyrazole-5-carboxamide, 4-[[2-Ethoxy-5-[(4-methyl-1-piper azinyl)sul fonyl]benzoyl]amino]-1-methyl-3-n-propyl;4-[2-Ethoxy-5-(4-methyl-1-piperazinylsulfonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide;4-[[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylbenzoyl]amino]-2-methyl-5-propylpyrazole-3-carboxamide
• CAS NO: 200575-15-1
• Molecular Formula: C₂₂H₃₂N₆O₅S
• Molecular Weight: 492.59
• Product Categories: Intermediates of Sildenafil
• Mol File: 200575-15-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 208-210℃
• Appearance: /
• Density: 1.37g/cm³
• Refractive Index: 1.637
• PKA: 11.93±0.70(Predicted)
• CAS DataBase Reference: 1H-PYRAZOLE-5-CARBOXAMIDE, 4-[[2-ETHOXY-5-[(4-METHYL-1-PIPERAZINYL)SULFONYL]BENZOYL]AMINO]-1-METHYL-3-PROPYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-PYRAZOLE-5-CARBOXAMIDE, 4-[[2-ETHOXY-5-[(4-METHYL-1-PIPERAZINYL)SULFONYL]BENZOYL]AMINO]-1-METHYL-3-PROPYL-(200575-15-1)
• EPA Substance Registry System: 1H-PYRAZOLE-5-CARBOXAMIDE, 4-[[2-ETHOXY-5-[(4-METHYL-1-PIPERAZINYL)SULFONYL]BENZOYL]AMINO]-1-METHYL-3-PROPYL-(200575-15-1)

Safety Data

• Hazardous Substances Data: 200575-15-1(Hazardous Substances Data)

Usage

Description

1H-PYRAZOLE-5-CARBOXAMIDE, 4-[[2-ETHOXY-5-[(4-METHYL-1-PIPERAZINYL)SULFONYL]BENZOYL]AMINO]-1-METHYL-3-PROPYLis a chemical compound with a complex structure, characterized by its unique arrangement of atoms and functional groups. It is an impurity found in Sildenafil, a medication used to treat erectile dysfunction.

Uses

Used in Pharmaceutical Industry:
1H-PYRAZOLE-5-CARBOXAMIDE, 4-[[2-ETHOXY-5-[(4-METHYL-1-PIPERAZINYL)SULFONYL]BENZOYL]AMINO]-1-METHYL-3-PROPYLis used as an impurity in the production of Sildenafil (S435000), an orally active selective type 5 cGMP phosphodiesterase inhibitor. Its presence is significant for quality control and ensuring the safety and efficacy of the final pharmaceutical product.

InChI:InChI=1/C22H32N6O5S/c1-5-7-17-19(20(21(23)29)27(4)25-17)24-22(30)16-14-15(8-9-18(16)33-6-2)34(31,32)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H2,23,29)(H,24,30)

Upstream product

• 139756-02-8 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 
• 194602-23-8 2-Ethoxy-5-(4-methylpiperazin-1-ylsulphonyl)benzoic acid 
• 383427-86-9 2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)benzonitrile 
• 200575-16-2 2-ethoxy-5-chlorosulphonyl-benzoic acid 
• 139756-01-7 1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carboxamide 
• 139756-00-6 1-methyl-2-nitro-3-propyl-1H-pyrazole-5-carboxylic acid 
• 139755-99-0 1-methyl-3-propyl-1 H-pyrazole-5-carboxylic acid 
• 134-11-2 2-ethoxybenzoic acid 
• 304435-83-4 4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester 
• 304435-81-2 [N'-(1-cyano-butyl)-N-methyl-hydrazino]-acetic acid ethyl ester 
• 17243-13-9 5-chlorosulfonyl-2-hydroxybenzoic acid 
• 109-01-3 1-methyl-piperazine 
• 64-67-5 diethyl sulfate 
• 960009-35-2 2-hydroxy-5-(4-methylpiperazin-1-ylsulphonyl)benzoic acid 

Downstream Products

• 139755-83-2 sildenafil 
• 139755-83-2 viagra 
• 1033861-39-0 7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine 

Relevant articles and documents

Preparation method of sildenafil citrate

The invention discloses a preparation method of sildenafil. The method comprises the following steps: activating an intermediate compound B in an aprotic solvent by using thionyl chloride, reducing with 1-methyl-4-nitro-3-propyl-1H-pyrazole-5-formamide in a zinc powder-ammonium chloride system in the presence of an acid-binding agent to obtain an intermediate compound E, and condensing to obtain an intermediate compound C; and cyclizing the intermediate compound C in an alcohol solvent under an alkaline condition to prepare sildenafil. The preparation method disclosed by the invention is short in reaction time, greatly shortens the production period so as to reduce the production cost, and is simple in operation and suitable for large-scale production.

Organic synthesis in a modular robotic system driven by a chemical programming language

The synthesis of complex organic compounds is largely a manual process that is often incompletely documented. To address these shortcomings, we developed an abstraction that maps commonly reported methodological instructions into discrete steps amenable to automation. These unit operations were implemented in a modular robotic platform by using a chemical programming language that formalizes and controls the assembly of the molecules. We validated the concept by directing the automated system to synthesize three pharmaceutical compounds, diphenhydramine hydrochloride, rufinamide, and sildenafil, without any human intervention. Yields and purities of products and intermediates were comparable to or better than those achieved manually. The syntheses are captured as digital code that can be published, versioned, and transferred flexibly between platforms with no modification, thereby greatly enhancing reproducibility and reliable access to complex molecules.

A method for preparing sildenafil

The invention discloses a preparation method of sildenafil and relates to the technical filed of chemical medicine synthesis. The method includes following steps: (1) carrying out a reaction between 2-ethyoxyl-5-(4-methylpiperazine-1-ylsulfonyl)benzoic acid with thionyl chloride in the presence of a catalyst to prepare an intermediate I; (2) carrying out a reaction between the intermediate I with 4-amino-1-methyl-3-propyl-1H-pyrazole-5-methanamide in the presence of an acid-binding agent to prepare an intermediate II; (3) carrying out a cyclization reaction to the intermediate II in the presence of a specific alkali to obtain a crude product of sildenafil; and (4) performing recrystallization to obtain a pure product of sildenafil. In the invention, reduced pressure distillation for removing exceeded thionyl chloride is unnecessary so that pollution is avoided. Meanwhile, the preparation method can reduce device investment, can simplify technology and can increase efficiency.