159724-40-0

Basic information

• Product Name: 3-(4-Morpholinyl)aniline
• Synonyms: 4-(3-Aminophenyl)morpholine;3-(Morpholin-4-yl)aniline 97+%;3-MORPHOLIN-4-YLANILINE;AKOS BB-8950;3-Morpholin-4ylaniline 97%;3-(4-Morpholinyl)aniline;3-Morpholin-4-yl-phenylamine;3-morpholinobenzenamine
• CAS NO: 159724-40-0
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 178.23
• Product Categories: Amines and Anilines;Heterocycles;pharmacetical;Amines;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 159724-40-0.mol

Chemical Properties

• Melting Point: 118 °C
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: /
• Density: 1.149g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated, Sonicated)
• PKA: 5.27±0.10(Predicted)
• CAS DataBase Reference: 3-(4-Morpholinyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-Morpholinyl)aniline(159724-40-0)
• EPA Substance Registry System: 3-(4-Morpholinyl)aniline(159724-40-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 22-36/37/39-26
• HazardClass: IRRITANT
• Hazardous Substances Data: 159724-40-0(Hazardous Substances Data)

Usage

Uses

3-Morpholin-4-ylaniline can be used to prevent and treat influenza.

InChI:InChI=1/C10H14N2O/c11-9-2-1-3-10(8-9)12-4-6-13-7-5-12/h1-3,8H,4-7,11H2

Upstream product

• 110-91-8 morpholine 
• 108-42-9 3-chloro-aniline 
• 99-09-2 3-nitro-aniline 
• 18437-64-4 tert-butyl (3-nitrophenyl)carbamate 
• 68621-88-5 (3-aminophenyl)carbamic acid tert-butyl ester 
• 1542259-01-7 tert-butyl (3-morpholinophenyl) carbamate 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 645-00-1 m-iodonitrobenzene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 585-79-5 m-nitrobromobenzene 
• 107-21-1 ethylene glycol 
• 626-01-7 3-Iodoaniline 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 116922-22-6 3-morpholinonitrobenzene 

Downstream Products

• 623153-08-2 C₂₈H₃₁N₇O₃ 
• 258864-15-2 4-methyl-3-nitro-N-(3-morpholinophenyl)benzamide 
• 947270-98-6 methyl 1-(3-morpholinophenyl)-5-phenyl-1H-imidazole-4-carboxylate 
• 1190377-79-7 cyclobutanecarboxylic acid {3-[5-cyclopropyl-2-(3-morpholin-4-yl-phenylamino)-pyrimidin-4-ylamino]-propyl}-amide 
• 1416336-73-6 6-bromo-1-[3-(4-morpholinyl)phenyl]-1H-benzimidazol-2-amine 
• 1416336-72-5 (2-amino-5-bromophenyl)[3-(4-morpholinyl)phenyl]amine 
• 1416334-10-5 5-(2-amino-1-(3-morpholinophenyl)-1H-benzo[d]imidazol-6-yl)-N-(tert-butyl)-2-methoxypyridine-3-sulfonamide 
• 1416336-71-4 5-bromo-N-[3-(4-morpholinyl)phenyl]-2-nitroaniline 
• 1421694-81-6 N₃-(3-morpholinophenyl)-N₅-(1-phenylethyl)-1,2,4-thiadiazole-3,5-diamine 
• 1314996-73-0 7-Amino-8-ethyl-2-(3-morpholin-4-ylphenylamino)-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamide 
• 1403885-72-2 (8-methoxy-3H-pyrazolo[3,4-c]quinolin-4-yl)-(3-morpholin-4-yl-phenyl)-amine 
• 1350816-00-0 9-chloro-2-(3-morpholinophenylamino)-5H-benzo[b]pyrimido[4,5-d]azepin-6(7H)-one hydrochloride 
• 1232398-34-3 [7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-morpholin-4-yl-phenyl)-amine 
• 1301134-18-8 N-[3-(3-{2-[(3-morpholin-4-ylphenyl)amino]pyrimidin-4-yl}imidazo[1,2-a]pyridin-2-yl)phenyl]-N'-phenylurea 

Relevant articles and documents

Transition-Metal-Catalyzed Amination of Aryl Fluorides

Arene activation via transition-metal (TM) η 6-coordination has merged as a powerful method to diversify the aromatic C-F bond, which is relatively less reactive due to its high bond energy. However, this strategy in general requires to use largely excess arenes or TM η 6-complexes as the substrates. Herein, we highlight our recent work on the catalytic S NAr amination of electron-rich and electron-neutral aryl fluorides that are inert in classical S NAr reactions. This protocol enabled by a Ru/hemilabile ligand catalyst covers a broad scope of substrates without wasting arenes. Mechanistic studies revealed that the nucleo?-philic substitution proceeded on a Ru η 6-arene complex, and the hemilabile ligand significant promoted the arene dissociation.

Rapid and Efficient Microwave-Assisted Amination of Electron-Rich Aryl Halides without a Transition-Metal Catalyst

Equation presented. A rapid and direct amination of aryl halides has been developed in good to high yields under microwave irradiation without a transition-metal catalyst. This reaction is a particularly powerful method for the coupling of electron-rich aryl halides with various amines. In some cases, the excellent regioselectivity could be observed, which facilitated the preparation of meta-substituted anilines from ortho- or para-substituted phenylhalides. In addition, a mechanism via the interesting benzyne intermediate has been proposed.

1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp2)-to-N Silyl Migration

The design, synthesis, and validation of 3-aminobenzyne precursors induced by C-(sp2)-to-N 1,3-aza-Brook rearrangement have been achieved, allowing access to diverse aniline derivatives. Through crossover experiments, we demonstrated the intramolecular mechanism of 1,3-C-to-N silyl transfer. To gain insight into the regioselectivity observed in the reactions, we performed density functional theory calculations. Finally, the method was applied to the synthesis of xylanigripones A in five linear steps in an overall yield of 30%.

NOTCH INHIBITORS AND USES THEREOF

Disclosed herein, inter alia, are compounds for inhibiting Notch and uses thereof.

Ru(II)-Catalyzed Amination of Aryl Fluorides via η6-Coordination

We developed a Ru/hemilabile-ligand-catalyzed nucleophilic aromatic substitution (SNAr) of aryl fluorides as the limiting reagents. Significant ligand enhancement was demonstrated by the engagement of both electron-rich and neutral arenes in the SNAr amination without using excess arenes. Preliminary mechanistic studies revealed that the nucleophilic substitution proceeds on a η6-complex of the Ru catalyst and the substrate, and the hemilabile ligand facilitates dissociation of products from the metal center.

Inter-alkane amidogen phenolic synthetic method (by machine translation)

Inter-alkane amidogen phenolic synthetic method, its characteristic is: 1st step, between the two alkane amidogen acyl aniline and sulfuric acid aqueous solution mixing and heating to 50 - 110 °C, thermal insulation reaction of aniline [...] sulfuric acid aqueous solution; 2nd step, continue to drip the sodium nitrite aqueous solution, sodium nitrite aqueous solution for dropping temperature of - 10 - 20 °C, drop bi yu 5 - 30 °C insulation, [...] aniline obtained diazonium salt of the sulfuric acid aqueous solution; 3rd step, [...] aniline diazonium salt of the sulfuric acid aqueous solution is directly heated to 45 - 110 °C, thermal insulation, in the hydrolysis reaction of the diazonium salt, cooling after treatment, to obtain the product between two alkane amidogen phenol; three-step required by the reaction of sulfuric acid in the 1st step reaction in the finished disposable adding; a three-step reaction in a finish step by step in the pot. The method of the invention with raw materials are cheap, abundant, synthetic high security of the process, the product yield is high, the three waste less pollution and the like, has high industrial value. (by machine translation)

DDX3X Helicase Inhibitors as a New Strategy to Fight the West Nile Virus Infection

Increased frequency of arbovirus outbreaks in the last 10 years represents an important emergence for global health. Climate warming, extensive urbanization of tropical regions, and human migration flows facilitate the expansion of anthropophilic mosquitos and the emerging or re-emerging of new viral infections. Only recently the human adenosinetriphosphatase/RNA helicase X-linked DEAD-box polypeptide 3 (DDX3X) emerged as a novel therapeutic target in the fight against infectious diseases. Herein, starting from our previous studies, a new family of DDX3X inhibitors was designed, synthesized, validated on the target enzyme, and evaluated against the West Nile virus (WNV) infection. Time of addition experiments after virus infection indicated that the compounds exerted their antiviral activities after the entry process, likely at the protein translation step of WNV replication. Finally, the most interesting compounds were then analyzed for their in vitro pharmacokinetic parameters, revealing favorable absorption, distribution, metabolism, and excretion values. The good safety profile together with a good activity against WNV for which no treatments are currently available, make this new class of molecules a good starting point for further in vivo studies.

Design and synthesis of potent dual inhibitors of JAK2 and HDAC based on fusing the pharmacophores of XL019 and vorinostat

Specifically blocking more than one oncogenic pathway simultaneously in a cancer cell with a combination of different drugs is the mainstay of the majority of cancer treatments. Being able to do this via two targeted pathways without inducing side effects through a general mechanism, such as chemotherapy, could bring benefit to patients. In this work we describe a new dual inhibitor of the JAK-STAT and HDAC pathways through designing and developing two types of molecule based on the JAK2 selective inhibitor XL019 and the pan-HDAC inhibitor, vorinostat. Both series of compounds had examples with low nanomolar JAK2 and HDAC1/6 inhibition. In some cases good HDAC1 selectivity was achieved while retaining HDAC6 activity. The observed potency is explained through molecular docking studies of all three enzymes. One example, 69c had 16–25 fold selectivity against the three other JAK-family proteins JAK1, JAK3 and TYK2. A number of compounds had sub-micromolar potencies against a panel of 4 solid tumor cell lines and 4 hematological cell lines with the most potent compound, 45h, having a cellular IC50 of 70 nM against the multiple myeloma cell line KMS-12-BM. Evidence of both JAK and HDAC pathway inhibition is presented in Hela cells showing that both pathways are modulated. Evidence of apoptosis with two compounds in 4 sold tumor cell lines is also presented.

Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates

A chemoselective sequential one-pot coupling protocol was developed for preparing several amino-anilines in high yield as building blocks for active pharmaceutical ingredients (APIs). Site (Cl vs Br on electrophile) and nucleophile (amine vs imine) selectivity is dictated by the catalyst employed. A Pd-crotyl(t-BuXPhos) precatalyst selectively coupled the Ar-Br of the polyhaloarene with benzophenone imine, even in the presence of a secondary amine, while Pd-based RuPhos or (BINAP)Pd(allyl)Cl coupled the Ar-Cl site with secondary amines.

DIARYLUREAS AS CB1 ALLOSTERIC MODULATORS

The present invention provides novel diarylurea derivatives (compounds of formula (I)) and their uses. The compounds of the present invention are demonstrated to be allosteric modulators of the CB1 receptor, and therefore useful for the treatment of diseases and conditions mediated by CB1.