587881-33-2

Usage

Uses

Used in Pharmaceutical Industry:
(R)-tert-butyl 1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropylcarbamate is used as a pharmaceutical compound for its potential therapeutic properties. Its unique chemical structure allows it to be explored for the development of novel drug treatments for various medical conditions, offering new possibilities for addressing unmet medical needs and improving patient outcomes.

Upstream product

• 587881-37-6 C₁₇H₂₁ClN₂O₄ 
• 100-46-9 benzylamine 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 22838-58-0 Boc-D-Val-OH 

Relevant academic research and scientific papers

Construction of N-Boc-2-Alkylaminoquinazolin-4(3H)-Ones via a Three-Component, One-Pot Protocol Mediated by Copper(II) Chloride that Spares Enantiomeric Purity

Chiral 2-alkylquinazolinones are key synthetic intermediates, but their preparation in high optical purity is challenging. Thus, a multicomponent procedure integrating anthranilic acids, N-Boc-amino acids, and amines in the presence of methanesulfonyl chl

Microwave assisted partial synthesis of enantiomerically pure s-ispinesib - A case study

Ispinesib, a quinazolinone derivative, is the first candidate that has entered clinical trials aimed at developing novel KSP inhibitors. It was discovered by Cytokinetics in a high-throughput screening effort followed by lead optimization of the identified KSP inhibitors. The synthetic route, which involved eleven steps, was problematic with an overall yield of only about 8%. Later a new synthetic strategy was developed which involved the introduction of the chiral center in the very first step using an enantiomerically pure amino acid which led to the synthesis of enantiomerically pure quinazolinones nucleus. Following this route, the yield rose to about 40 % together with a reduction in the manufacturing cost. Present study is the first ever reinvestigation of the partial synthesis of enantiomerically pure ispinesib under microwave irradiation by optimizing the reaction conditions for two bottleneck steps of the synthesis of ispinesib via two routes. The aim of study was to reduce the reaction time and the number of steps and then scale-up the microwave synthesis to synthesize multigrams of ispinesib by using continuous flow processing approach. Route 1 involves the synthesis of quinazolinone core under MW irradiation in a one-pot, two-step reaction sequence using D-valine while Route 2 takes into account N-alkylation of D-valine methyl ester via reductive amination prior to the formation of quinazolinone nucleus.