590424-05-8

Basic information

• Product Name: N-[2-(DiethylaMino)ethyl]-2,4-diMethyl-1H-pyrrole-3-CarboxaMide
• Synonyms: N-[2-(DiethylaMino)ethyl]-2,4-diMethyl-1H-pyrrole-3-CarboxaMide
• CAS NO: 590424-05-8
• Molecular Formula: C₁₃H₂₃N₃O
• Molecular Weight: 237.34122
• Mol File: 590424-05-8.mol

Chemical Properties

• Boiling Point: 372.5°C at 760 mmHg
• Flash Point: 179.1°C
• Appearance: /
• Density: 1.029g/cm³
• Vapor Pressure: 9.6E-06mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 15.43±0.46(Predicted)
• CAS DataBase Reference: N-[2-(DiethylaMino)ethyl]-2,4-diMethyl-1H-pyrrole-3-CarboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(DiethylaMino)ethyl]-2,4-diMethyl-1H-pyrrole-3-CarboxaMide(590424-05-8)
• EPA Substance Registry System: N-[2-(DiethylaMino)ethyl]-2,4-diMethyl-1H-pyrrole-3-CarboxaMide(590424-05-8)

Safety Data

• Hazardous Substances Data: 590424-05-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-[2-(Diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-Carboxamide is used as a potential drug candidate for its pharmacological properties, particularly in the development of new medications. Its unique structure and activity make it a subject of interest for researchers exploring novel therapeutic agents.
Used in Anticancer Applications:
In the field of oncology, N-[2-(Diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-Carboxamide is studied for its potential as an anti-cancer agent. Its specific effects on cancer cells and mechanisms of action are under investigation, with the aim of identifying its role in inhibiting tumor growth or enhancing the effectiveness of existing cancer treatments.
Used in Central Nervous System Research:
N-[2-(Diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-Carboxamide is also being explored for its effects on the central nervous system. Its potential use in treating neurological disorders or modulating neurotransmission is a significant area of research, given the compound's ability to interact with components of the nervous system.
Used in Medicinal Chemistry:
In the realm of medicinal chemistry, N-[2-(Diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-Carboxamide serves as a key compound in the design and synthesis of new pharmaceuticals. Its structural features are utilized to create derivatives with improved pharmacological profiles, potentially leading to more effective and safer drugs.

InChI:InChI=1/C13H23N3O/c1-5-16(6-2)8-7-14-13(17)12-10(3)9-15-11(12)4/h9,15H,5-8H2,1-4H3,(H,14,17)

Upstream product

• 590424-04-7 tert-butyl 4-[[[2-(diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate 
• 100-36-7 N,N-diethylethylenediamine 
• 682341-85-1 3-(1H-Imidazol-1-ylcarbonyl)-2,4-dimethyl-1H-pyrrole 
• 590424-03-6 N-[2-(diethylamino)ethyl]-3-oxobutanamide 
• 17106-13-7 2,4-dimethyl-1H-pyrrole-3-carboxylic acid 

Downstream Products

• 557795-19-4 sunitinib 
• 342641-94-5 sunitinib 
• 341031-54-7 sunitinib malate 
• 356068-86-5 N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide 

Relevant articles and documents

High-purity L-sunitinib malate preparation method

The present invention discloses a high-purity L-sunitinib malate preparation method, which comprises the following reaction route defined in the specification, wherein the step a comprises that a B5 compound and 5-fluoroindol-2-one are subjected to an Aldol condensation reaction to obtain a sunitinib free base (B6 compound), the step b comprises that the B6 compound and L-malic acid are subjected to a salt forming reaction to obtain the L-sunitinib malate, and the step a and the step b are performed in a dark place. According to the present invention, the HPLC purity of the prepared L-sunitinib malate can achieve more than 99.8%, the single impurity content can be controlled at less than 0.1%, and the quality difficulty of the application of the L-sunitinib malate in the preparation is effectively solved.

PROCESS FOR THE PREPARATION OF N-[2-DIETHYLAMINO)ETHYL]-5-[(5-FLUORO-1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)METHYL]-2,4-DIMETHYL-1H-PYRROLE-3-CARBOXAMIDE

The present invention relates to processes for the preparation of N-[2-(Diethylamino) ethyl]-5-[ (5-fluoro-1, 2 -dihydro-2-oxo-3H-indol-3-ylidene) methyl] -2, 4-dimethyl-I H-pyrrole- 3 -carboxamide of formula (VI).

Method of synthesizing indolinone compounds

Disclosed are methods of preparing pyrrole compounds of formula 14 and indolinone compounds of formula 1 via a synthetic route wherein the amide sidechain on the pyrrole moiety is attached prior to pyrrole formation. The compounds 14 produced by the methods herein are useful in the synthesis of compounds of formula 1, which are useful in the treatment of abnormal cell growth, such as cancer.

Synthesis of [18F]SU11248, a new potential PET tracer for imaging cancer tyrosine kinase

N-[2-(Diethylamino)ethyl]-5-[(Z)-(5-[18F]fluoro-2-oxo-1, 2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide, a new potential positron emission tomography tracer for imaging cancer tyrosine kinase, has been prepared by the nucleophilic substitution of the nitro-precursor N-[2-(diethylamino)ethyl]-5-[(Z)-(5-nitro-2-oxo-1,2-dihydro-3H- indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide with K 18F/Kryptofix 2.2.2 followed by a simple chromatography methodology combined solid-phase extraction with high-performance liquid chromatography purification procedures in 15-25% radiochemical yields.

Method for catalyzing amidation reactions

The invention provides a method of preparing a compound of formula 2 wherein R1 and R6 are as defined herein, by a catalytic amidation process in the presence of added carbon dioxide. The inventive methods show surprising rate enhancement relative to the corresponding uncatalyzed reaction.

Amidations Using N,N′-Carbonyldiimidazole: Remarkable Rate Enhancement by Carbon Dioxide

Carbon dioxide catalyzes the reaction of imidazolides with amines to form amides. A substantial rate enhancement is observed in the presence of CO 2 compared to the CO2-free case. The scope and limitations of this reaction are discussed.

Early amidation approach to 3-[(4-amido)pyrrol-2-yl]-2-indolinones

A new synthesis of 3-[(4-amido)pyrrol-2-yl]-2-indolinones has been developed, where the amide side chain was installed prior to pyrrole formation. This strategy precludes the need to use any coupling reagents to install the amide side chain. This process includes a zinc-free alternative to the Knorr pyrrole synthesis.