7470-38-4

Usage

Uses

Used in Organic Synthesis:
4-Morpholinobenzoic acid is used as an intermediate in organic synthesis, playing a crucial role in the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its ability to form a wide range of derivatives makes it a valuable building block in the synthesis of complex molecules.
Used in Water-Based Additives Industry:
In the water-based additives industry, 4-Morpholinobenzoic acid is utilized as a heat-sealing and anti-blocking agent. Its properties allow it to improve the performance of materials in various applications, such as packaging films and other plastic products, by enhancing their heat-sealing capabilities and preventing them from sticking to each other during the manufacturing process.

InChI:InChI=1/C11H13NO3/c13-11(14)9-1-3-10(4-2-9)12-5-7-15-8-6-12/h1-4H,5-8H2,(H,13,14)

Upstream product

• 110-91-8 morpholine 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 23676-05-3 4-morpholin-4-yl-benzoic acid methyl ester 
• 19614-15-4 4-(morpholin-4-yl)benzoic acid ethyl ester 
• 586-76-5 4-Bromobenzoic acid 
• 1204-86-0 4-(4-morpholinyl)benzaldehyde 
• 934012-95-0 2-ethyl-4-fluorobenzonitrile 
• 1194-02-1 4-fluorobenzonitrile 
• 655-32-3 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone 
• 70783-44-7 2,2,2-trifluoro-1-(4-morpholin-4-yl-phenyl)-ethanone 
• 10282-31-2 4-morpholinobenzonitrile 

Downstream Products

• 1030830-17-1 C₂₂H₂₇N₃O₄ 
• 438248-78-3 N-[4-Methyl-3-(2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]-4-morpholino-benzamide 
• 197445-59-3 (R)-N-[8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide 
• 1029431-06-8 C₃₆H₄₄N₆O₇ 
• 720720-60-5 4-(3-oxomorpholin-4-yl)benzoic acid 
• 1057647-23-0 N-{2-[4-(3-oxomorpholin-4-yl)benzoylamino]benzyl}-5-chlorothiophene-2-carboxamide 
• 1400001-40-2 N-(2-methoxyethyl)-3-[4-(morpholin-4-yl)phenyl][1,2,4]triazolo[4,3-b]pyridazin-6-amine 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of a series of novel 2-benzamide-4-(6-oxy-N-methyl-1-naphthamide)-pyridine derivatives as potent fibroblast growth factor receptor (FGFR) inhibitors

Starting from the phase II clinical FGFR inhibitor lucitanib (2), we conducted a medicinal chemistry approach by opening the central quinoline skeleton coupled with a scaffold hopping process thus leading to a series of novel 2-benzamide-4-(6-oxy-N-methyl-1-naphthamide)-pyridine derivatives. Compound 25a was identified to show selective and equally high potency against FGFR1/2 and VEGFR2 with IC50 values less than 5.0 nM. Significant antiproliferative effects on both FGFR1/2 and VEGFR2 aberrant cancer cells were observed. In the SNU-16 xenograft model, compound 25a showed tumor growth inhibition rates of 25.0% and 81.0% at doses of 10 mg/kg and 50 mg/kg, respectively, with 5% and 10%body weight loss. In view of the synergistic potential of FGFs and VEGFs in tumor angiogenesis observed in preclinical studies, the FGFR/VEGFR2 dual inhibitor 25a may achieve better clinical benefits.

Buchwald-Hartwig amination reaction of aryl halides using heterogeneous catalyst based on Pd nanoparticles decorated on chitosan functionalized graphene oxide

In this work, graphene oxide was functionalized with chitosan (GO-Chit) followed by a simple approach for immobilization of palladium nanoparticles onto a chitosan grafted graphene oxide surface. The Pd-nanocomposite (GO-Chit-Pd) was characterized using Transmission Electron Microscopy (TEM), Fourier transforms infrared spectroscopy (FT-IR), and X-ray diffraction (XRD) measurements. The catalytic activity of the prepared heterogeneous graphene oxide functionalized chitosan-palladium (GO-Chit-Pd) was investigated in term of C-N coupling reaction (Buchwald-Hartwig amination reaction of aryl halides) yielding products of N-arylamines. The easy purification, convenient operation, and environmental friendliness, combined with a high yield, render this method viable for use in both laboratory research and larger industrial scales. Studying the reusability of the catalyst in this work showed that it could be reused for five times without obvious loss in catalytic activity.

Novel 4-(morpholin-4-yl)-N′-(arylidene)benzohydrazides: Synthesis, antimycobacterial activity and QSAR investigations

A series of 4-(morpholin-4-yl)-N′-(arylidene)benzohydrazides were synthesized using appropriate synthetic route. Antimycobacterial activity of the synthesized compounds (5a-5j) was carried out and percentage reduction in relative light units (RLU) was calculated using luciferase reporter phages (LRP) assay. Percentage reduction in relative light units (RLU) for isoniazid was also calculated. The test compounds showed significant antitubercular activity against Mycobacterium tuberculosis H37Rv and clinical isolates: S, H, R, and E resistant M. tuberculosis, when tested in vitro. Quantitative structure-activity relationship (QSAR) investigation with 2D-QSAR analysis was applied to find a correlation between different experimental or calculated physicochemical parameters of the compounds studied and 3D-QSAR analysis and to indicate the exact steric and electronic requirements in the ranges at various positions around pharmacophore. In general Schiff bases exhibit antimycobacterial activity and morpholine ring is important for antimicrobial activity. So we have synthesized 10 different 4-(morpholin-4-yl)-N′-(arylidene)benzohydrazides. The structures of new compounds were characterized by TLC, FTIR, 1H NMR, mass spectral data and elemental analysis. Amongst the compounds tested 5d and 5c were found to be the most potent, while 5i, 5e, and 5j were found to have an average activity against M. tuberculosis H37Rv and 5a, 5f, 5h, 5g, and 5b were found to have a greater activity against clinical isolates: S, H, R, and E resistant M. tuberculosis as compared to M. tuberculosis H37Rv.

Study of the microwave-assisted hydrolysis of nitriles and esters and the implementation of this system in rapid microwave-assisted Pd-catalyzed amination

Microwave-assisted hydrolysis of benzonitriles and methyl benzoates has been studied using a toluene/concd aq KOH two phase system in the presence and absence of phase transfer catalyst. Conditions to allow and avoid smooth hydrolysis could be identified. Based on the latter, the first microwave protocol which allows the rapid Pd-catalyzed amination of aliphatic amines with chlorobenzenes containing sensitive functional groups has been developed.

A practical method for the preparation of 4-nitrogen-substituted benzoic acids

An efficient and practical method for the preparation of 4-nitrogen-substituted benzoic acids is described. Our method consists of the aromatic substitution of 2,2,2,4′-tetrafluoroacetophenone with amines, followed by haloform reaction to the benzoic acids. In this method, even though for the less nucleophilic 7-, 8-, and 9-membered amines 1 equiv. was used, corresponding benzoic acids were obtained in moderate to excellent yield. As the experimental procedure including purification is simple, this method is applicable to large-scale syntheses. Copyright

3,4-Disubstituted azetidinones as selective inhibitors of the cysteine protease cathepsin K. Exploring P3 elements for potency and selectivity

The synthesis of a series of highly potent and selective inhibitors of cathepsin K based on the 3,4-disubstituted azetidin-2-one warhead is reported. A high degree of potency and selectivity was achieved by introducing a basic nitrogen into the distal par

Antithrombotic amides

This application relates to a compound of formula (I) (or a pharmaceutically acceptable salt thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermidates thereof.

Process for the synthesis of morpholinylbenzenes

A new improved process for synthesizing morpholinylbenzenes of the formula I by reacting morpholine of II with a substituted benzene of formula III, wherein morpholine is used as a reactant and as the only one solvent.