The Production Process of 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylicacid

The Production Process of 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylicacid

1. Introduction

1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylicacid, also known as Compound X, is an important drug compound that has been shown to have potent antiviral activity against various strains of the coronavirus.
Its chemical structure is composed of various functional groups, including a cyclopropyl ring, a fluorine atom, a methoxy group, a hydroxyl group, a nitrogen atom, and a quinoline group.
The synthesis of Compound X requires the use of various reagents and chemicals, and the process typically involves a series of reaction steps that are carefully optimized to achieve the desired yield and purity of the final product.

2. Raw Materials and Reagents

The synthesis of Compound X typically involves the use of a variety of raw materials and reagents, including organic solvents, bases, acids, and various reagents for the introduction of functional groups.
These raw materials and reagents are carefully selected to ensure their compatibility and to minimize the risk of contamination.

3. The First Step - Preparation of 6-Chloro-2H-pyrrolo[3,4-b]pyridine-3-carboxylic acid

The first step in the synthesis of Compound X involves the preparation of 6-chloro-2H-pyrrolo[3,4-b]pyridine-3-carboxylic acid.
This is typically accomplished by treating a 2H-pyrrolo[3,4-b]pyridine-3-carboxylic acid precursor with an appropriate chlorinating agent.
The precursor is first dissolved in an appropriate solvent, such as dichloromethane, and the chlorinating agent is added to the solution.
The reaction mixture is then typically stirred for several hours at room temperature, after which time the reaction is quenched with an appropriate base, such as sodium carbonate.
The resulting mixture is then separated using standard chromatography techniques, such as column chromatography or high-performance liquid chromatography (HPLC), to isolate the desired product.

4. The Second Step - Preparation of 8-Methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid

The second step in the synthesis of Compound X involves the preparation of 8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid.
This is typically accomplished by treating 6-chloro-2H-pyrrolo[3,4-b]pyridine-3-carboxylic acid with an appropriate methoxylating agent, such as methyl iodide or dimethyl sulfate.
The reaction is typically carried out in the presence of a solvent, such as acetonitrile or dichloromethane, and a base, such as sodium hydroxide or potassium hydroxide.
The reaction mixture is then typically stirred for several hours at room temperature, after which time the reaction is quenched with an appropriate acid, such as hydrochloric acid or sulfuric acid.
The resulting mixture is then