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(4S)-4-(4-Cyano-2-methoxyphenyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxamide is an organic compound that finds applications in various fields, including pharmaceuticals, agrochemicals, and chemical synthesis.
The compound is synthesized through several synthetic routes, each with its own advantages and limitations.
In this article, we will discuss some of the commonly used synthetic routes for the synthesis of (4S)-4-(4-Cyano-2-methoxyphenyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxamide.
- Reaction of 4-chloro-2-methoxyaniline with 2-(methoxymethyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxylic acid
One of the most commonly used synthetic routes for the synthesis of (4S)-4-(4-Cyano-2-methoxyphenyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxamide is through the reaction of 4-chloro-2-methoxyaniline with 2-(methoxymethyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxylic acid.
This reaction is commonly known as a Puckered-Ullmann condensation and provides the desired product in good yield.
- Reaction of 4-cyanofenyl magnesium bromide with 2-(methoxymethyl) -5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxylic acid
Another synthetic route for the synthesis of (4S)-4-(4-Cyano-2-methoxyphenyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxamide is the reaction of 4-cyanofenyl magnesium bromide with 2-(methoxymethyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxylic acid.
This reaction is known as a Grignard reaction and provides the desired product in good yield.
- Reaction of N-bromosuccinimide with 2-(methoxymethyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxylic acid
N-bromosuccinimide can also be used as a reagent in the synthesis of (4S)-4-(4-Cyano-2-methoxyphenyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxamide.
The reaction involves the nucleophilic substitution of the bromide ion in N-bromosuccinimide with the active methylene group in 2-(methoxymethyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxylic acid, providing the desired product in good yield.
- Reaction of 4-chloro-2-methoxyaniline with 2-(methoxymethyl)-5-ethoxy-1,4-dihydro-2,8-dim
