18137-25-2

Usage

Uses

Used in Pharmaceutical Industry:
CHEMBRDG-BB 5581642 is used as a key intermediate in the synthesis of morpholine benzamides, which are drugs used for the treatment of neuropsychiatric disorders. Its unique chemical structure allows it to interact with specific targets in the nervous system, providing therapeutic benefits for patients suffering from such conditions.

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

Upstream product

• 160816-43-3 4-(4-morpholinylcarbonyl)-benzoic acid 
• 110-91-8 morpholine 
• 106-41-2 4-bromo-phenol 
• 201230-82-2 carbon monoxide 
• 540-38-5 p-Iodophenol 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 99-96-7 4-hydroxy-benzoic acid 
• 100743-91-7 4-(4-acetoxy-benzoyloxy)-benzoic acid ethyl ester 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 110007-32-4 4-ethoxycarbonylphenyl 4-hydroxybenzoate 
• 402-45-9 4-hydroxybenzotrifluoride 
• 2345-34-8 4-acetyloxy-benzoic acid 
• 557-21-1 dicyanozinc 
• 820232-27-7 3-bromo-4-hydroxymorpholinobenzamide 

Downstream Products

• 634903-80-3 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-[4-(4-morpholinylcarbonyl)phenyl]-1-benzothiophene-2-carboxamide hydrochloride 
• 634904-42-0 N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-7-[4-(4-morpholinylcarbonyl)phenyl]-1-benzothiophene-2-carboxamide hydrochloride 
• 634904-13-5 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-[4-(morpholinylcarbonyl)phenyl]-1-benzofuran-2-carboxamide hydrochloride 
• 1160829-27-5 C₂₄H₃₀BNO₅ 
• 634905-13-8 4-(morpholine-4-carbonyl)phenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

Morpholine benzamide compound and application thereof

The invention belongs to the field of medical treatment, and particularly relates to a morpholine benzamide compound and application thereof, the morpholine benzamide compound has a compound structureshown as a formula (A), and the compound can be applied

Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

We report a new visible-light-mediated carbonylative amidation of aryl, heteroaryl, and alkyl halides. A tandem catalytic cycle of [Ir(ppy)2(dtb-bpy)]+ generates a potent iridium photoreductant through a second catalytic cycle in the presence of DIPEA, which productively engages aryl bromides, iodides, and even chlorides as well as primary, secondary, and tertiary alkyl iodides. The versatile in situ generated catalyst is compatible with aliphatic and aromatic amines, shows high functional-group tolerance, and enables the late-stage amidation of complex natural products.

Synthesis, biological evaluation and molecular modeling study of 2-amino-3,5-disubstituted-pyrazines as Aurora kinases inhibitors

Serine/threonine protein kinases Aurora A, B, and C play essential roles in cell mitosis and cytokinesis, and a number of Aurora kinase inhibitors have been evaluated in the clinic. Herein we report the synthesis and their antiproliferation of 3,5-disubstituted-2-aminopyrazines as kinases inhibitors. Amongst, 4-((3-amino-6- (3,5-dimethylisoxazol-4-yl)pyrazin-2-yl)oxy)-N-(3-chlorophenyl) benzamide (12Aj) exhibited the strongest antiproliferative activities against U38, HeLa, HepG2 and LoVo cells with IC50 values were 11.5 ± 3.2, 1.34 ± 0.23, 7.30 ± 1.56 and 1.64 ± 0.48 μM, as well as inhibited Aurora A and B with the IC50 values were 90 and 152 nM, respectively. Molecular docking studies indicated that 12Aj appeared to form stable hydrogen bonds with either Aurora A or Aurora B. Furthermore, 12Aj arrested HeLa cell cycle in G2/M phase by regulating protein levels of cyclinB1 and cdc2. In addition, the bioinformatics prediction further revealed that 12Aj possessed good drug likeness using SwissADME. These results suggested that 12Aj was worthy of future development of potent anticancer agents as pan-Aurora kinases.

An efficient procedure for chemoselective amidation from carboxylic acid and amine (ammonium salt) under mild conditions

Presented here is an efficient one-pot and catalyst-free procedure for the synthesis of amides starting from carboxylic acids and amine/ammonium salts using 2,2-dichloro-1,3-diisopropylimidazolidine-4,5-dione as the coupling agent. Reactions can proceed smoothly even with those bearing thermosensitive group(s) at ambient temperature, and the corresponding products of primary, secondary and tertiary amides can be afforded in moderate to excellent yields of up to 96%.

Model experiments implicate a benzoquinoneketene intermediate in LCP synthesis

LCP synthesis from 4-hydroxybenzoic acid (HBA) and comonomers involves the formation of phenolic anion end groups at the later stages of polymerization. Model reactions show that these end groups can undergo cleavage to form 4-oxo-2,5-cyclohexadienylideneketene OCK (a benzoquinoneketene intermediate) with loss of a resonance-stabilized phenolic anion. With base, ethyl 4-(4′-hydroxybenzoyloxy)benzoate formed ethyl 4-hydroxybenzoate and poly-HBA, while ethyl 4-(4′-methoxybenzoyloxy)benzoate did not react under the same conditions, indicating an E1cB mechanism involving OCK as an intermediate. Attempted trapping of the OCK intermediate using cycloadditions failed, but it was successfully trapped with secondary amines. These results make it likely that LCP synthesis occurs at least partly via OCK. It is a ubiquitous intermediate in LCP polymerization and characterization.

Synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups

Figure presented In this paper, a novel synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups is presented. Anionically activated trifluoromethyl groups react with secondary amines under aqueous conditions to afford tertiary amides. The mechanism involves initial elimination of hydrogen fluoride by an E1cB mechanism to afford an electrophilic quinone methide- or azafulvene-type intermediate that reacts with secondary amines under aqueous conditions to afford the tertiary amide in good yield (up to 99%).

A practical synthesis of highly functionalized aryl nitriles through cyanation of aryl bromides employing heterogeneous Pd/C

An industrially viable cyanation of aryl bromides with Zn(CN)2 was accomplished in the presence of inexpensive and readily accessible Pd/C, Zn dust, ZnBr2, and PPh3 in DMA to provide functionalized aryl nitriles in moderate to high yields.

A practical synthesis of highly functionalized aryl nitriles through cyanation of aryl bromides employing heterogeneous Pd/C: In quest of an industrially viable process

Preparation of aryl nitrile 2a through classical Rosenmund-von Braun reaction of aryl bromide 1a resulted in a poor yield (61%) due to a high reaction temperature (165°C) and a lack of efficient procedure for separating 2a from a large quantity of heavy metal waste (Cu salts). To address these issues, a practical synthesis of multifunctional aryl nitriles through cyanation of aryl bromides has been developed with heterogeneous Pd/C used as the catalyst. Treatment of aryl bromides 1 with Zn(CN)2 in the presence of Pd/C, Zn, ZnBr2 and PPh3 in DMA provided aryl nitriles 2 involving those carrying sterically demanding electron-rich substituent in good yields and in highly reproducible manner. The activity of Pd/C is highly dependent on the properties of the Pd/C. Oxidic thickshell type catalyst Pd/C D5 was found to furnish the highest rate acceleration and yield. The use of heterogeneous Pd/C might anchor and disperse Pd over the solid support of the catalyst, at least in the initial stage of the reaction, to assure the formation of monomeric Pd complex without precipitating to inactive Pd black. The use of a slightly excess of Zn(CN)2 (0.6 equiv) and air oxidation of phosphine ligand, after end of the reaction, converted Pd species to insoluble phosphine-free Pd cyanides, from which Pd was recovered in high yield through simple filtration followed by usual recovery process involving combustion.

Synthesis of 4-(4-guanidinobenzoyloxy)benzamides and 1-(4-guanidinobenzoyloxy)benzoyloxy acetamides as trypsin inhibitors

Seventeen new compounds of 4-(4-guanidinobenzoyloxy)benzamides and 4-(4-guanidinobenzoyloxy)benzoyloxyacetamides were prepared and their inhibitory activities on trypsin, thrombin and porcine pancreatic elastase were measured. These compounds were found to be selective trypsin inhibitors with inhibiting activities from 0.44 to 43 μM.