The Instruction 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 synthesis of novel compounds is a continual process in the chemical industry.
In recent years, researchers have been focusing on the development of new drugs to treat various diseases, including cancer.
One such compound that has gained attention is 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.

This compound, commonly referred to as CX-804, is a novel, selective inhibitor of the BRD4 protein.
BRD4 has been identified as a key regulator of gene expression in hematologic cancers, and its inhibition has been shown to have anti-tumor effects in both in vitro and in vivo models.

The synthesis of CX-804 involves a multistep process that requires the manipulation of various functional groups.
The synthesis of these groups is critical to the final product, and the steps involved in the synthesis are complex and require careful execution.

Step 1: Synthesis of N-Cyclopropyl-N-(2-(4-fluorophenyl)chroman-6-yl)amide
The first step in the synthesis of CX-804 involves the preparation of N-cyclopropyl-N-(2-(4-fluorophenyl)chroman-6-yl)amide.
This is achieved by reacting cyclopropylamine with 2-(4-fluorophenyl)chroman-6-one in the presence of a suitable catalyst, such as triethylamine.
The reaction is carried out under standard conditions for amide formation, such as trifluoroacetic acid, and the product is isolated by standard chromatographic methods.

Step 2: Synthesis of N-Cyclopropyl-N-(6-bromo-2-(4-fluorophenyl)chroman-8-yl)amide
The next step involves the synthesis of N-cyclopropyl-N-(6-bromo-2-(4-fluorophenyl)chroman-8-yl)amide.
This is achieved by reacting N-cyclopropyl-N-(2-(4-fluorophenyl)chroman-6-yl)amide with 6-bromo-2-(4-fluorophenyl)chroman-8-one in the presence of a suitable catalyst, such as DMAP.
The reaction is carried out under standard conditions for amide formation, such as hydrochloric acid, and the product is isolated by standard chromatographic methods.

Step 3: Synthesis of N-Cyclopropyl-N-(7aR-2-(4-fluorophenyl)chroman-6,8-dione)
The next step involves the synthesis of N-cyclopropyl-N-(7aR-2-(4-fluorophenyl)chroman-6,8-dione.
This is achieved by reacting N-cyclopropyl-N-(6-bromo-2-(4-fluorophenyl)chroman-8-yl)amide with thionyl chloride in the presence of a suitable catalyst, such as DMF.
The reaction is carried out under standard conditions for thionyl chloride, and the product is isolated by standard chromatographic methods.

Step 4: Synthesis of N-Cyclopropyl-N-(7aR-1,2,4aR-octahydro-8-methoxy-5H-pyrrolo[3,4-b]pyridin-6-yl)acetamide
The final step in the synthesis of CX-804 involves the synthesis of N-cyclopropyl-N-(7aR-1,2,4aR-octahydro-8-methoxy-5H-pyrrolo[3,4-b]pyridin-6-yl)acetamide.
This is achieved by reacting N-cyclopropyl-N-(7aR-2-(4-fluorophenyl)chroman-6,8-dione with 1,2,4aR-octahydro-8-methoxy