226070-47-9

Basic information

• Product Name: 5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester
• Synonyms: 5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester;tert-Butyl 5-hydroxyisoindoline-2-carboxylate;N-Boc-5-hydroxyisoindoline;2H-Isoindole-2-carboxylic acid, 1,3-dihydro-5-hydroxy-, 1,1-dimethylethyl ester
• CAS NO: 226070-47-9
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235
• Mol File: 226070-47-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester(226070-47-9)
• EPA Substance Registry System: 5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester(226070-47-9)

Safety Data

• Hazardous Substances Data: 226070-47-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester is used as a key intermediate in the synthesis of resorcylate aminopyrazole compounds. These compounds are known as Hsp90 inhibitors, which play a crucial role in the development of novel therapeutic strategies for various diseases, including cancer.
Used in Preparation of Hsp90 Inhibitors:
5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester is used as a starting material for the preparation of Hsp90 inhibitors. Hsp90 (Heat shock protein 90) is a molecular chaperone that plays a significant role in the stabilization and activation of various client proteins involved in cellular signaling pathways. Inhibition of Hsp90 has been shown to have potential therapeutic benefits in the treatment of cancer and other diseases by disrupting the function of its client proteins.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 54544-67-1 5-hydroxyisoindoline 
• 105358-58-5 5-hydroxy-isoindoline hydrobromide 
• 905273-91-8 tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate 
• 127168-84-7 5-bromoisoindoline 
• 6941-75-9 5-Bromoisoindoline-1,3-dione 
• 127168-88-1 5-methoxy-2,3-dihydro-1H-isoindole 
• 201940-08-1 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 
• 50727-06-5 5-hydroxy-isoindole-1,3-dione 

Downstream Products

• 437650-82-3 methanesulfonic acid 2-[2-(4-tert-butoxycarbonylamino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindol-5-yl ester 
• 437651-10-0 {4-[2-(5-cyano-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester 
• 437652-01-2 methanesulfonic acid 2-[2-(4-amino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindol-5-yl ester 
• 437652-04-5 2-[2-(4-amino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindole-5-carbonitrile 
• 263888-56-8 tert-butyl 5-cyanoisoindoline-2-carboxylate 
• 263888-60-4 5-methanesulfonyloxy-2,3-dihydro-1H-isoindole 
• 263888-58-0 5-cyano-2,3-dihydro-1H-isoindole 

Relevant articles and documents

APPLICATION OF MONOCYCLIC BETA-LACTAM COMPOUND IN PHARMACY

An application of a compound represented by formula (I) and pharmaceutically acceptable salts thereof in preparation of a drug for treating pneumonia.

MONOCYCLIC B-LACTAM COMPOUND FOR TREATING BACTERIAL INFECTION

Disclosed are a class of new monocyclic β-lactam compounds, an isomer thereof or pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising the compounds, and the use of same in preparing drugs for treating diseases associated

Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water

A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.

Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions

The combination of Cu(acac)2 and N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) provides a powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively low temperatures (80 and 60 °C, respectively) at low catalytic loadings (0.5 mol % Cu).

1,3-DIHYDROISOINDOLE DERIVATIVES

Novel 1,3-dihydroisoindole derivatives of the formula (I), in which R1-R3 have the meanings indicated in claim 1, areHSP90 inhibitors and can be used for the preparation of a medicament for the treatment of diseases in which the inhibition, regulation and/or modulation of HSP90 plays a role.

INDAZOLAMIDE DERIVATIVES

Novel indazole derivatives of the formula (I), in which R1-R3 have the meanings indicated in claim 1, are HSP90 inhibitors and can be used for the preparation of a medicament for the treatment of diseases in which the inhibition, regulation and/or modulation of HSP90 plays a role.

ISOINDOLE DERIVATIVES

This invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof, a process of making these compounds, pharmaceutical compositions containing one or more of these compounds or their salts, and their use for the treatment of schizophrenia, bipolar disorder, or other central nervous system disorders.

Design and synthesis of novel 2,3-dihydro-1H-isoindoles with high affinity and selectivity for the dopamine D3 receptor

Starting from the tetrahydroisoquinoline SB-2770111, a novel series of 5-substituted-2,3-dihydro-1H-isoindoles has been designed. Subsequent optimisation resulted in identification of 19. which has high affinity for the dopamine D3 receptor (pKi 8.3) and ≥ 100-fold selectivity over other aminergic receptors. In rat studies 19 was brain penetrant with an excellent pharmacokinetic profile (oral bioavailability 77%. t1/2 5.2h).