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

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

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

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

Downstream Products

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

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.

Efficient and Practical Synthesis of Sulfonamides Utilizing SO2 Gas Generated on Demand

A simple and practical protocol was developed for the synthesis of sulfonamides by reacting organometallic reagents with SO2 gas generated on demand. SO2 was generated from readily available reagents safely in a highly contained and controlled fashion. The protocol allows the synthesis of sulfonamides without using either atom-inefficient SO2 surrogates or a SO2 cylinder that requires stringent storage regulations in the laboratory. The protocol was successfully applied to the synthesis of sildenafil.

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 kind of improved sildenafil preparation method (by machine translation)

The invention relates to an improved sildenafil preparation method, characterized in that sildenafil is represented by the formula IV compound in the alkaline aqueous solution under the conditions of the cyclization reaction preparation, formula IV compound is represented by the formula I compound with a chloro formate form the active mixed anhydride (II), its without separation and purification directly reacted with compound III. The method for preparing sildenafil yield and high purity, low cost, and easy industrial production: . (by machine translation)

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.

Polymer-supported reagents for multi-step organic synthesis: Application to the synthesis of sildenafil

Sildenafil 1 (Viagra(TM)), a well known and commercially important pharmaceutical drug, has been prepared using polymer-supported reagents in a multi-step, convergent process resulting in a clean and efficient preparation without the need for conventional purification methods. (C) 2000 Elsevier Science Ltd.

The chemical development of the commercial route to sildenafil: A case history

This paper is a case history of the chemical development of sildenafil which covers various aspects of work in chemical development namely: route selection, scale-up issues, the development of an efficient synthesis with high throughput, process safety, and environmental issues. Interesting chemical points include improved methods of preparing pyrazolo[4,3-d]-pyrimidines and the unusual isolation of an intermediate as its double salt (10). The potential dangers of nitrating pyrazole-5-carboxylic acids which are activated to a decarboxylation reaction are discussed.

Process for preparing sildenafil

A process for the preparation of a compound of formula (I): STR1 which comprises cyclization of a compound of formula (II): STR2