157368-82-6

Basic information

• Product Name: 1,2-Benzisoxazol-3-amine,6-methoxy-(9CI)
• Synonyms: 1,2-Benzisoxazol-3-amine,6-methoxy-(9CI);6-Methoxybenzo[d]isoxazol-3-aMine;3-Amino-6-methoxy-1,2-benzisoxazole;6-Methoxy-benzo[d]isoxazol-3-ylamine
• CAS NO: 157368-82-6
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16132
• Product Categories: OXAZOLE
• Mol File: 157368-82-6.mol

Chemical Properties

• Boiling Point: 348.9±22.0 °C(Predicted)
• Appearance: /
• Density: 1.304±0.06 g/cm3(Predicted)
• PKA: 2.92±0.30(Predicted)
• CAS DataBase Reference: 1,2-Benzisoxazol-3-amine,6-methoxy-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Benzisoxazol-3-amine,6-methoxy-(9CI)(157368-82-6)
• EPA Substance Registry System: 1,2-Benzisoxazol-3-amine,6-methoxy-(9CI)(157368-82-6)

Safety Data

• Hazardous Substances Data: 157368-82-6(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry Research:
1,2-Benzisoxazol-3-amine,6-methoxy-(9CI) is used as a research compound for exploring its potential biological activities and pharmacological properties. Its unique structure and chemical properties make it a promising candidate for the development of new therapeutic agents.
Used in Drug Discovery and Development:
In the pharmaceutical industry, 1,2-Benzisoxazol-3-amine,6-methoxy-(9CI) is utilized as a lead compound in drug discovery and development processes. Its potential role as a therapeutic agent is being investigated for the treatment of various diseases and conditions, making it a valuable asset in the search for novel medications.
Used in Chemical Synthesis:
1,2-Benzisoxazol-3-amine,6-methoxy-(9CI) can also be used as a building block or intermediate in the synthesis of more complex organic compounds and pharmaceuticals. Its unique structure and reactivity make it a useful component in the creation of new molecules with potential applications in various fields.

Upstream product

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Relevant articles and documents

AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF A7-NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to novel aminobenzisoxazole compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of ot7-nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

Application of aryloximes as solid-phase ketone linkers.

In both solution and the solid phase, a variety of ketone oxime anions have been treated with 4-substituted-2-fluorobenzonitriles to give the corresponding nucleophilic aromatic substitution aryloxime adducts. Under aqueous acidic conditions, these adducts underwent cyclization to give the corresponding ketones. Suzuki and amide coupling reactions were also successfully performed on two resin-bound oximes followed by subsequent cyclorelease to give ketone product in good yields and purities. [reaction--see text]

Preparation of 2-hydroxybenzamidines from 3-aminobenzisoxazoles

2-Hydroxybenzamidines have been prepared from 3-aminobenzisoxazoles by reductive cleavage of the nitrogen-oxygen bond using catalytic hydrogenation, Zn/AcOH or NiCl2/NaBH4. This ring-opening reaction can be accomplished chemoselectively in the presence of a variety of hydrogenation-sensitive functional groups including an aryl bromide, benzyl carbamate, and olefin.

Studies on the synthetic compatibility of aryloxime linkers in the solid-phase synthesis of 3-aminobenzisoxazoles

Further exploration of the scope of our solid-phase method for the synthesis of 3-aminobenzisoxazoles (using the Kaiser oxime resin 1) is described. The effects of base, leaving group, and solvent on the nucleophilic aromatic substitution based resin-loading reaction are discussed. Representative aryloxime intermediates were subjected to a variety of acidic conditions commonly used in protecting group removal to establish the acid stability profile of this linker. Regioselectivity was evaluated with various di- and trifluorobenzonitriles, which gave single benzisoxazole products after loading and cyclorelease reactions. Substituent effects observed in the course of the acid stability and regioselectivity studies suggest that the nitrile plays a critical role in the oxime hydrolysis mechanism. Finally, to establish the compatibility of the aryloxime linker with a variety of useful on-resin synthetic transformations, functionalized substrates were loaded onto resin 1, and carbon-nitrogen, carbon-oxygen, and carbon-carbon bond-forming reactions were successfully executed.

Novel one-pot cyclization of ortho substituted benzonitriles to 3-amino-1,2-benzisoxazoles

A novel one-pot synthesis of 3-amino-1,2-benzisoxazoles (iii), from ortho substituted benzonitriles (i), is described. The synthesis likely involves a SNAr reaction of an activated ortho halo or nitro group by a hydroxamate anion, followed by an intra-mol

Substituted 3-(aminoalkylamino)-1,2-benzisoxazoles and related compounds

This application relates to compounds of the formula STR1 wherein R1, X, Y and n are as defined in the specification; and pharmaceutically acceptable addition salts thereof and optical and geometric isomers or racemic mixtures thereof; which co