One-Pot Triazine Synthesis Eliminating Mutagenic Intermediate Isolation
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Solution Overview
Problem
Conventional methods for producing 3-oxo-5-substituted triazine compounds require extensive purification and isolation procedures, leading to inefficiencies and safety concerns due to the use of mutagenic and sublimable intermediates, making large-scale industrial production challenging.
Innovation Solution
A method involving the reaction of a compound with a glyoxalization reagent, followed by reaction with aminourea in water, and subsequent cyclization under basic conditions to produce 3-oxo-5-substituted triazine with high purity, using water as a solvent and eliminating the need for intermediate isolation through filtration of precipitates.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional methods are used to produce 3-oxo-5-substituted triazine, then the product can be obtained, but extensive purification and isolation procedures are required, leading to time loss and reduced productivity
Solution Approach 1:
The invention combines multiple reaction steps (glyoxal derivative formation, aminourea reaction, and cyclization) into a one-pot sequential process where intermediates are not isolated. The reaction mixture proceeds directly from one step to the next, merging what were previously separate purification-intensive steps into a continuous process that achieves high purity final product without intermediate handling.
Solution Approach 2:
The invention performs preliminary actions by adding all reagents (glyoxalization reagent, aminourea, and base) in sequence at the beginning of the one-pot reaction. This allows the reaction to proceed through multiple stages without intermediate intervention, preventing the need for purification steps between stages while maintaining product purity.
2Manufacturing precision
If conventional methods with intermediate isolation are used, then purification can be achieved, but the process becomes complex and time-consuming
Solution Approach 1:
The invention merges the formation of glyoxal derivative, its reaction with aminourea, and the subsequent cyclization into a single integrated reaction system. By eliminating the need to isolate and purify intermediates between these steps, the device complexity is dramatically reduced while the final product purity is maintained through the controlled sequential reaction pathway.
3Manufacturing precision
If intermediates are isolated and purified in conventional methods, then high purity product can be obtained, but worker safety is compromised due to handling of mutagenic and sublimable compounds
Solution Approach 1:
The invention performs all necessary transformations in a sealed one-pot system without requiring workers to handle, isolate, or purify mutagenic intermediates. The preliminary addition of all reagents and the continuous reaction process eliminates exposure to harmful substances while maintaining product purity through controlled reaction conditions.
Solution Approach 2:
The invention extracts the harmful intermediates from the worker environment by keeping them contained within the reaction vessel throughout the process. Instead of isolating these mutagenic compounds for purification, the method allows them to remain in the reaction mixture where they continuously transform into the final safe product, eliminating worker exposure.
4Manufacturing precision
If multiple isolation procedures are performed in conventional methods, then intermediate purity can be maintained, but production cost increases due to additional steps
Solution Approach 1:
The invention merges multiple separate manufacturing steps into a single one-pot operation, eliminating the need for repeated filtration, drying, and purification equipment usage. This consolidation maintains intermediate purity through controlled reaction conditions while significantly reducing manufacturing costs by removing redundant processing steps.
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
This method enables the efficient and safe production of 3-oxo-5-substituted triazine with high purity, reducing the need for time-consuming purification steps and improving worker safety by avoiding the handling of mutagenic intermediates, thus being industrially advantageous in terms of both cost and safety.
Implementation Method 1
reacting the resulting imine derivative or a salt thereof with a base in water to produce the compound represented by formula I or a salt thereof
Implementation Method 2
the purity of the target 3-oxo-5-substituted triazine may be easily improved by optionally collecting the imine derivative or a salt thereof by filtration from the reaction mixture
Data Source
AI summary
The present invention provides an industrially advantageous method for producing a 3,5-disubstituted triazine compound that is useful as an active pharmaceutical ingredient. More specifically, the present invention provides a production method, whereby it becomes possible to efficiently produce a 3-oxo-5-substituted triazine in water without the need to isolate an intermediate that may have mutagenicity, and it also becomes possible to perform the production without the need to isolate a product in each of multiple steps. Namely, the present invention provides a method for producing a compound represented by formula I or a salt thereof, the method including a step of reacting a compound represented by the following formula IV or a salt thereof with a base in water, and optionally including a step of forming a salt thereof. Specifically, the present invention provides a method for producing a compound represented by formula I or a salt thereof, the method including a step of derivatizing a compound represented by formula II or a salt thereof into a corresponding compound represented by formula III, a salt thereof, or a derivative thereof, then a step of reacting the resulting compound, a salt thereof, or a derivative thereof with aminourea or a salt thereof in water to produce a compound represented by formula IV or a salt thereof, and then a step of reacting the resulting compound or a salt thereof in the presence of a base.(wherein ring A represents an optionally substituted aryl group or an optionally substituted heteroaryl group)