177995-39-0

Basic information

• Product Name: 6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE
• Synonyms: 6-broMo-1,2-benzoxazol-3-aMine;3-AMino-6-broMobenzo[d]isoxazole;6-Bromo-1,2-benzisoxazol-3-amine;1,2-Benzisoxazol-3-amine,6-bromo-;6-BROMOBENZO[D]ISOXAZOL-3-AMINE
• CAS NO: 177995-39-0
• Molecular Formula: C₇H₅BrN₂O
• Molecular Weight: 213.03
• Mol File: 177995-39-0.mol

Chemical Properties

• Boiling Point: 371.101°C at 760 mmHg
• Flash Point: 178.236°C
• Appearance: /
• Density: 1.805g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.716
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.72±0.30(Predicted)
• CAS DataBase Reference: 6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE(177995-39-0)
• EPA Substance Registry System: 6-BROMOBENZO[D]ISOXAZOL-3-YLAMINE(177995-39-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 177995-39-0(Hazardous Substances Data)

Usage

Uses

6-Bromobenzo[D]Isoxazol-3-Amine is a useful research reagent for organic synthesis.

InChI:InChI=1/C7H5BrN2O/c8-4-1-2-5-6(3-4)11-10-7(5)9/h1-3H,(H2,9,10)

Upstream product

• 546-88-3 acetylhydroxamic acid 
• 179897-89-3 5-Bromo-2-fluoro-benzonitrile 
• 105942-08-3 4-bromo-6-fluorobenzonitrile 

Downstream Products

• 1257211-39-4 (S)-tert-butyl 2-(5-(4-(3-aminobenzo[d]isoxazol-6-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate 
• 915301-13-2 (6-bromo-benzo[d]isoxazol-3-yl)-(4-tert-butyl-benzyl)-amine 
• 45744-18-1 hydroxybenzamidine 

Relevant articles and documents

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.

Enhanced treatment regimens using mTor inhibitors

The present invention provides for methods and pharmaceutical compositions comprising inhibitors of mTorC1 and/or mTorC2. In some aspects, the invention provides for treatment regimens resulting in enhanced treatment efficacy and better tolerability.

COMBINATION OF KINASE INHIBITORS AND USES THEREOF

The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth. The present invention also provides a pharmaceutical kit effective for treating a disease condition associated with PI3 -kinase α and/or mTOR in a subject.

COMBINATION PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

The present invention provides for methods and pharmaceutical compositions for treating proliferative disorders. In one aspect, the method comprises administration of two cell-cycle suppressors having a synergistic effect. In another aspect, two cell-cycle suppressors having a synergistic effect are provided in a pharmaceutical composition.

Application of a recyclable fluorous oxime in the convenient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines

A microwave-assisted, fluorous synthetic route to 3-amino-1,2- benzisoxazoles and 4-amino-1H-2,3-benzoxazines has been developed. The strategy comprises linking the respective 2-fluorobenzonitrile or 2-(bromomethyl) benzonitrile to a fluorous oxime tag to give an aryloxime intermediate which then undergoes cyclization with concomitant cleavage of the substrate-tag in acidic conditions to provide the desired product in good to moderate yields. In addition, the aryloxime intermediate could be subjected to further reactions to expand the compound library. The product could be easily separated using fluorous solid-phase extraction (F-SPE) and the fluorous ketone recovered could be converted back to the fluorous oxime and reused in the next run of the synthesis.

BENZOXAZOLE KINASE INHIBITORS AND METHODS OF USE

The present invention provides chemical entities or compounds and pharmaceutical compositions thereof that are capable of modulating certain protein kinases such as mTor, tyrosine kinases, and/or lipid kinases such as PI3 kinase. Also provided in the present invention are methods of using these compositions to modulate activities of one or more of these kinases, especially for therapeutic applications.

Raf inhibitor compounds and methods of use thereof

Compounds of Formula I are useful for inhibiting Raf kinase and for treating disorders mediated thereby. Methods of using compounds of Formula I, and stereoisomers, geometric isomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

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.