36263-51-1

Usage

Chemical Properties

colorless to yellow-brown low melting solid

InChI:InChI=1/C14H17NO/c1-16-13-7-5-12(6-8-13)14(11-15)9-3-2-4-10-14/h5-8H,2-4,9-10H2,1H3

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 15057-00-8 1-trimethylsilylcyclohexanecarbonitrile 
• 766-05-2 cyclohexane carbonitrile 
• 111-24-0 1,5-dibromo-pentane 
• 104-47-2 p-methoxybenzylnitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 17138-79-3 1-(4-methoxyphenyl)cyclohexanol 
• 20758-60-5 1-(4-methoxyphenyl)cyclohexene 
• 459-60-9 1-fluoro-4-methoxybenzene 

Downstream Products

• 7469-83-2 1-(4-methoxyphenyl)cyclohexane-1-carboxylic acid 
• 868849-59-6 1-(4-hydroxy-phenyl)-cyclohexanecarbonitrile 
• 613-36-5 4-cyclohexylanisole 
• 56140-77-3 1-(4-methoxyphenyl)cyclohexane-1-carbaldehyde 
• 36970-20-4 1-aminomethyl-1-(4-methoxyphenyl)cyclohexane 
• 1429442-65-8 (1-(4-methoxyphenyl)cyclohexyl)(phenyl)methanone 
• 1429442-40-9 (S)-2-((S)-1,1-dimethylethylsulfinamido)-N,N-diethyl-2-(1-(4-methoxyphenyl)cyclohexyl)-2-phenylacetamide 
• 1429442-39-6 (S)-N-((1-(4-methoxyphenyl)cyclohexyl)(phenyl)methylene)-2-methylpropane-2-sulfinamide 

Relevant academic research and scientific papers

N2-(2-METHOXYPHENYL)PYRIMIDINE DERIVATIVE, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION FOR CANCER PREVENTION OR TREATMENT CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a N2-(2-methoxyphenyl)pyrimidine derivative, a preparation method thereof, and a pharmaceutical composition for the prevention or treatment of cancer comprising the same as an active ingredient. The N2-(2-methoxyphenyl)pyrimidine derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention is very effective in suppressing anaplastic lymphoma kinase (ALK) activity and as a result it can improve the effectiveness of treatment on cancer cells having anaplastic lymphoma kinase (ALK) fusion proteins such as EML4-ALK and NPM-ALK, so that it can be effectively used as a pharmaceutical composition for preventing or treating cancer.

Hydride Reduction by a Sodium Hydride-Iodide Composite

Sodium hydride (NaH) is widely used as a Br?nsted base in chemical synthesis and reacts with various Br?nsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar π electrophiles. This study presents a series of reduction reactions of nitriles, amides, and imines as enabled by NaH in the presence of LiI or NaI. This remarkably simple protocol endows NaH with unprecedented and unique hydride-donor chemical reactivity.

Pd-catalyzed α-arylation of nitriles and esters and γ-arylation of unsaturated nitriles with TMPZnCl?LiCl

Using TMPZnCl?LiCl as a kinetically highly active base, nitriles and esters undergo a Pd-catalyzed α-arylation under mild conditions. Remarkably, in the case of α,β- or β,γ-unsaturated nitriles, a regioselective γ-arylation or a γ-alkenylation is observed.

Broonsted acid-promoted hydrocyanation of arylalkenes

Nonactivated arylalkenes are effectively converted to tertiary benzylic nitriles in the presence of triflic acid and trimethylsilyl cyanide. The hydrocyanation reactions result in good to excellent yield when electron-donating groups are substituted on the benzene ring. The reaction conditions are mild and relatively safe, notably without need for handling hazardous hydrogen cyanide gas, providing simple and easy access to tertiary benzylic nitriles. The reaction was applied to the preparation of a PDE4 inhibitor (3) as well as a series of analogues.

Facile preparation of α-aryl nitriles by direct cyanation of alcohols with TMSCN under the catalysis of InX3

(Chemical Equation Presented) A convenient and efficient synthesis of α-aryl nitrites was developed by direct cyanation of alcohols with TMSCN under the catalysis of Lewis acid. Using 5-10 mol % of InBr3 as the catalyst, a variety of benzylic alcohols can be converted to the corresponding nitriles in 5-30 min with yields of 46-99%.

Mild palladium-catalyzed selective monoarylation of nitriles

Two new palladium-catalyzed procedures for the arylation of nitriles under less basic conditions than previously reported have been developed. The selective monoarylation of acetonitrile and primary nitriles has been achieved using α-silyl nitriles in the presence of ZnF2. This procedure is compatible with a variety of functional groups, including cyano, keto, nitro, and ester groups, on the aryl bromide. The arylation of secondary nitriles occurred in high yield by conducting reactions with zinc cyanoalkyl reagents. These reaction conditions tolerated base-sensitive functional groups, such as ketones and esters. The combination of these two methods, one with a-silyl nitriles and one with zinc cyanoalkyl reagents, provides a catalytic route to a variety of benzylic nitriles, which have not only biological significance but utility as synthetic intermediates. The utility of these new coupling reactions has been demonstrated by a synthesis of verapamil, a clinically used drug for the treatment of heart disease, by a three-step route from commercial materials that allows convenient variation of the aryl group.

CARBAMIC ACID COMPOUNDS COMPRISING AN ESTER OR KETONE LINKAGE AS HDAC INHIBITORS

This invention pertains to certain carbamic acid compounds of the formula (I), which inhibit HDAC (histone deacetylase) activity: wherein: J is a linking functional group and is independently: -O-C(=O)- or -C(=O)-O- or - C(=O)-; Cy is a cyclyl group and is independently: C3-20carbocyclyl, C3-20heterocyclyl, or C5-20aryl; and is optionally substituted; Q1 is a cyclyl leader group, and is independently a divalent bidentate group obtained by removing two hydrogen atoms from a ring carbon atom of a saturated monocyclic hydrocarbon having from 4 to 7 ring atoms, or by removing two hydrogen atoms from a ring carbon atom of saturated monocyclic heterocyclic compound having from 4 to 7 ring atoms including 1 nitrogen ring atom or 1 oxygen ring atom; and is optionally substituted; Q2 is an acid leader group, and is independently: C1-8alkylene; and is optionally substituted; or: Q2 is an acid leader group, and is independently: C5-20arylene; C5-20arylene-C1-7alkylene; C1-7alkylene-C5-20arylene; or C1-7alkylene-C5-20arylene-C1-7alkylene; and is optionally substituted; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC,and in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, etc.