220860-50-4

Basic information

• Product Name: 1,5-Naphthyridine-3-carboxamide, 6-ethoxy-1,4-dihydro-4-oxo-N-(phenylmethyl)-
• CAS NO: 220860-50-4
• Molecular Formula: C18H17N3O3
• Molecular Weight: 323.351
• Mol File: 220860-50-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,5-Naphthyridine-3-carboxamide, 6-ethoxy-1,4-dihydro-4-oxo-N-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Naphthyridine-3-carboxamide, 6-ethoxy-1,4-dihydro-4-oxo-N-(phenylmethyl)-(220860-50-4)
• EPA Substance Registry System: 1,5-Naphthyridine-3-carboxamide, 6-ethoxy-1,4-dihydro-4-oxo-N-(phenylmethyl)-(220860-50-4)

Safety Data

• Hazardous Substances Data: 220860-50-4(Hazardous Substances Data)

Usage

Chemical class

Naphthyridine derivatives

Structure

Contains a naphthyridine ring with a carboxamide group at the 3-position

Substituents

Ethoxy at the 6-position and phenylmethyl at the N-position

Functional group

Carbonyl group at the 4-position

Potential reactivity

Presence of a carbonyl group suggests possible reactivity

Biological activity

May have potential pharmacological properties due to its structural features

Applications

Potential pharmaceutical applications

Interest in research

May be of interest for further study in medicinal chemistry and drug development

Upstream product

• 92808-33-8 6-ethoxy-4-oxo-1,4-dihydro[1,5]naphthyridine-3-carboxylic acid ethyl ester 
• 100-46-9 benzylamine 

Relevant articles and documents

PROCESS FOR THE PREPARATION AND PURIFICATION OF 1,5-NAPHTHYRIDINE-3-CARBOXYAMIDES

A new route for the preparation and purification of substituted 1,5-naphthyridine-3-carboxyamides, useful in the diagnosis and treatment of anxiety, Downs Syndrome, sleep, cognitive and seizure disorders, and overdose with benzodiazepine drugs and for enhancement of alertness, is provided. These compounds may be readily prepared by treating the corresponding 1,5-naphthyridine-3-carboxylic acids with a primary amine and a 1,1-carbonyldiimidazole. Purification is achieved by converting the substituted 1,5-naphthyridine-3-carboxyamides to a salt with a strong base such as potassium t-butoxide, recrystallizing and acidifying to regenerate the pure carboxyamide.

Synthesis and Purification of 6-Ethoxy-4-oxo-1,4-dihydro-[1,5] naphthyridine-3-carboxylic Acid Benzylamide

The synthesis of 6-ethoxy-4-oxo-1,4-dihydro-[1,5]naphthyridine-3- carboxylic acid benzylamide (1) on multikilogram scale is described. The major challenge for the synthesis of this quinolone GABA partial agonist was in the isolation of product of acceptable purity for clinical studies due to the insolubility of this compound. Also described are efforts to circumvent a high-temperature cyclization required for the synthesis of the quinolone ring system.