Preparation and application of a 5-bromoquinazoline derivative

Patent metadata

Field	Value
Publication number	US-11840537-B2
Application number	US-202117488317-A
Country	US
Kind code	B2
Filing date	Sep 29, 2021
Priority date	Nov 3, 2020
Publication date	Dec 12, 2023
Grant date	Dec 12, 2023

Abstract

A 5-bromoquinazoline derivative (I), structural formula thereof is as follows:

the synthesis method thereof comprises weighing 1.18 g of 5-bromoisatin, 2.5503 g of ammonium formate and 100 ml of absolute methanol in a 250 mL round-bottom flask, heating, stirring and refluxing for 48 h, stopping reaction, rotating to obtain 1.6033 g of filter residue crude product, carrying out column chromatography separation by using dichloromethane and absolute methanol according to a volume ratio of 1:1, and obtaining a target crystal compound I; the application of the 5-bromoquinazoline derivative compound crystal (I), as a catalyst has a good catalytic effect in nitrile silicification reaction of benzaldehyde and auto-polymerization reaction of benzophenone hydrazone, the conversion rates thereof respectively reach 39% and 76%, and the crystal (I) can be used as an anti-cancer reagent which has certain anti-cancer activity of breast cancer, liver cancer and lung cancer.

First claim

The invention claimed is:

1. A 5-bromoquinazoline derivative (I), structural formula thereof is as follows:

2. The 5-bromoquinazoline derivative crystal (I) of claim 1 , at the temperature of 293(2) K, and on the Oxford X-ray single crystal diffractometer, diffraction data is collected by w-O scanning mode with MoKα rays (λ=0.71073 Å) monochromatized by a graphite monochromator, wherein the crystal belongs to the triclinic system, P-1, cell parameters: a=8.7881(5) Å alpha=98.254(2)deg; b=9.9375(5) Å beta=97.014(2)deg; c=17.8389(9) Å gamma=112.154deg.

3. A synthesis method of the 5-bromoquinazoline derivative compound (I) of claim 1 , comprising heating 5-bromoisatin and ammonium formate in absolute methanol to obtain the final product.

4. A method of synthesizing benzyloxy-trimethylsilane, comprising reacting benzaldehyde and TMSCN with a catalyst of formula (I) according to claim 1 in THF at room temperature to obtain the product.

5. A method of synthesizing 1,2-bis(diphenylmethylene)hydrazine, comprising heating a reaction of benzophenone hydrazone with a catalyst of formula (I) according to claim 1 in methanol to obtain the product.

Assignees

• Luo Mei
• Univ Hefei Technology

Inventors

• Luo Mei

Classifications

• C07D487/10 Primary

  Spiro-condensed systems · CPC title

• C07B41/04

  of ether, acetal or ketal groups · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• B01J31/0271

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0231 · CPC title