Titanium(IV) Isopropoxide Mediated Solution Phase Reductive Amination on an Automated Platform: Application in the Generation of Urea and Amide Libraries

Title: Titanium(IV) Isopropoxide Mediated Solution Phase Reductive Amination on an Automated Platform: Application in the Generation of Urea and Amide Libraries

Volume: 3 Issue: 2

Author(s): Sukanta Bhattacharyya, Lisa Fan, Lanchi Vo and Jeff Labadie

Affiliation:

Keywords: Titanium(IV) Isopropoxide, Mediated Solution Phase Reductive Amination, Automated Platform, Urea, 96 Ureas, Sulfonamides

Abstract: Amine libraries and their derivatives are important targets for high throughput synthesis because of their versatility as medicinal agents and agrochemicals. As a part of our efforts towards automated chemical library synthesis, a titanium(IV) isopropoxide mediated solution phase reductive amination protocol was successfully translated to automation on the Trident ä library synthesizer of Argonaut Technologies. An array of 24 secondary amines was prepared in high yield and purity from 4 primary amines and 6 carbonyl compounds. These secondary amines were further utilized in a split synthesis to generate libraries of ureas, amides and sulfonamides in solution phase on the Trident. The automated runs included 192 reactions to synthesize 96 ureas in duplicate and 96 reactions to synthesize 48 amides and 48 sulfonamides. A number of polymer-assisted solution phase protocols were employed for parallel work-up and purification of the products in each step.

Cite this article as:

Bhattacharyya Sukanta, Fan Lisa, Vo Lanchi and Labadie Jeff, Titanium(IV) Isopropoxide Mediated Solution Phase Reductive Amination on an Automated Platform: Application in the Generation of Urea and Amide Libraries, Combinatorial Chemistry & High Throughput Screening 2000; 3 (2) . https://dx.doi.org/10.2174/1386207003331760