Imidazopyrrolidinone Synthesis via Segmented Coupling
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Solution Overview
Problem
Existing processes for preparing imidazopyrrolidinone derivatives face challenges in scaling up due to safety issues, loss of process control, and generation of hazardous waste, making them unsuitable for full-size production.
Innovation Solution
A modified process using less hazardous chemicals and reaction conditions, involving specific solvents, bases, and coupling agents, such as N,N'-carbonyldiimidazole, to enhance efficiency and yield, while reducing impurities and side reactions, as described in the provided schemes.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If existing processes are scaled up for full-size production, then productivity increases, but safety issues and loss of process control worsen
Solution Approach 1:
The synthesis process is divided into multiple discrete steps with isolated workups and purifications between each step. This segmentation allows for better control at each stage, reduced accumulation of hazards, and easier scalability compared to one-pot reactions.
Solution Approach 2:
The patent introduces specific intermediates and workup procedures between reaction steps that serve as buffers to control the overall process. These intermediates allow for controlled progression through the synthesis pathway, enabling scale-up while maintaining process reliability.
2Productivity
If existing processes are scaled up for full-size production, then productivity increases, but generation of hazardous waste increases
Solution Approach 1:
The patent converts potentially hazardous byproducts into useful intermediates or recyclable materials. Specific workup procedures are designed to transform harmful substances into benign or valuable products, reducing waste generation while maintaining high productivity at scale.
Solution Approach 2:
The synthesis process incorporates steps to recover and reuse valuable materials while properly disposing of hazardous waste. Recyclable intermediates are recovered through specific purification steps, and hazardous byproducts are managed through designated disposal procedures, enabling scalable production with reduced environmental harm.
3Ease of manufacture
If conventional chemicals and conditions are used, then ease of manufacture is maintained, but safety and hazard issues worsen
Solution Approach 1:
The patent modifies reaction parameters such as temperature, pressure, concentration, and pH to use safer chemicals and conditions. These parameter changes maintain manufacturing ease while reducing chemical hazards, allowing for safe scale-up without sacrificing process simplicity.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The process allows for scalable, reproducible, and safer production of high-quality imidazopyrrolidinone derivatives with reduced waste and lower costs, suitable for commercial production scales.
Implementation Method 1
reacting a compound of formula (D6), or a salt thereof, or a solvate thereof, in a solvent in the presence of base and a coupling agent, wherein the coupling agent is N,N'-carbonyldiimidazole
Data Source
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AI summary
The present disclosure relates to a method of synthesizing imidazopyrrolidinone derivative, such as compound of formula (I), or a solvate including hydrate thereof, or a co-crystal thereof, and/or intermediates thereof, their use as pharmaceuticals and the use of intermediates.