The Synthetic Routes of 2-[3-[4-(1H-Indazol-5-ylamino)-2-quinazolinyl]phenoxy]-N-(1-methylethyl)acetamide

2-[3-[4-(1H-Indazol-5-ylamino)-2-quinazolinyl]phenoxy]-N-(1-methylethyl)acetamide is an organic compound that has gained significant attention in recent years due to its potential application in various fields such as pharmaceuticals, agrochemicals, and dyes.

The compound can be synthesized through various routes, each of which has its advantages and disadvantages.
In this article, we will discuss three synthetic routes of 2-[3-[4-(1H-Indazol-5-ylamino)-2-quinazolinyl]phenoxy]-N-(1-methylethyl)acetamide.

Route 1: Via in situ formation of the indazol-5-ylamino quinazoline derivative from 4-(1H-Indazol-5-ylamino)-2-quinazoline and 2-[3-(dicyclohexylamino)phenyl]acetamide in the presence of a base such as sodium hydroxide (NaOH) and in the presence of a solvent such as N,N-dimethylacetamide (DMA).

This route involves the formation of the indazol-5-ylamino quinazoline derivative via a reaction between 4-(1H-Indazol-5-ylamino)-2-quinazoline and 2-[3-(dicyclohexylamino)phenyl]acetamide in the presence of a base such as NaOH.
The reaction is then continued in the presence of a solvent such as DMA.
The resulting intermediate is then reacted with N-methylmethanesulfonamide (MMMS) and 1-methylethylchloride in the presence of a base such as sodium hydride (NaH) to afford the desired product.

Advantages: This route is simple and offers good yields of the desired product.

Disadvantages: The reaction involves several steps, and the use of a base such as NaOH can be hazardous.

Route 2: Via in situ formation of the indazol-5-ylamino quinazoline derivative from 4-(1H-Indazol-5-ylamino)-2-quinazoline and 2-[3-(dicyclohexylamino)phenyl]acetamide in the presence of a solvent such as N,N-dimethylacetamide (DMA) and in the presence of a Lewis acid such as zinc iodide (ZnI2).

This route also involves the formation of the indazol-5-ylamino quinazoline derivative via a reaction between 4-(1H-Indazol-5-ylamino)-2-quinazoline and 2-[3-(dicyclohexylamino)phenyl]acetamide in the presence of a solvent such as DMA.
The reaction is then continued in the presence of a Lewis acid such as ZnI2.
The resulting intermediate is then reacted with N-methylmethanesulfonamide (MMMS) and 1-methylethylchloride in the presence of a base such as sodium hydride (NaH) to afford the desired product.

Advantages: This route is simple and offers good yields of the desired product.

Disadvantages: The use of a Lewis acid such as ZnI2 can be hazardous.

Route 3: Via in situ formation of the indazol-5-ylamino quinazoline derivative from 4-(1H-Indazol-5-ylamino)-2-quinazoline and 2-[3-(dicyclohexylamino)phenyl]acetamide in the presence of a solvent such as N,N-dimethylformamide (DMF) and in the presence of a base such as triethylamine (TEA) and a catalyst such as Pd/C.

This route involves the formation of the indazol-5-ylamino quinazoline derivative via a reaction between 4-(1H-Indazol-5-ylamino)-2-quinazoline and 2-[3-(dicyclohexylamino)phenyl]ac