6342-64-9

Usage

Preparation

Obtained by reaction of methylmagnesium bromide with 5-chloro-2-methoxybenzoyl chloride in the presence of bis[2-(N,N-dimethylamino)ethyl] ether in THF at –5° to 0° (69%).

InChI:InChI=1/C9H9ClO2/c1-6(11)8-5-7(10)3-4-9(8)12-2/h3-5H,1-2H3

Upstream product

• 623-12-1 4-chloromethoxybenzene 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 75-16-1 methylmagnesium bromide 
• 29568-33-0 2-methoxy-5-chlorobenzoyl chloride 
• 579-74-8 2-Methoxyacetophenone 
• 55877-79-7 2-methoxy-5-chlorobenzonitrile 
• 876-27-7 4-chlorophenyl acetate 
• 74-88-4 methyl iodide 

Downstream Products

• 3438-16-2 5-chloro-2-methoxybenzoic acid 
• 861349-33-9 1-(5-chloro-2-methoxy-phenyl)-butane-1,3-dione 
• 111841-05-5 2-bromo-1-(5-chloro-2-methoxyphenyl)-ethanone 
• 934340-26-8 C₁₃H₁₂ClNO₄ 
• 934340-38-2 C₁₅H₁₄ClNO₅ 
• 934340-41-7 C₁₆H₁₆ClNO₅ 
• 69316-10-5 3-(5-chloro-2-methoxyphenyl)-3-oxopropanenitrile 
• 13726-24-4 2-Methoxy-5-chlor-phenylacetylhomoveratrylamin 
• 917107-30-3 2-(5-chloro-2-methoxy-phenyl)-1-morpholin-4-yl-ethanethione 
• 1029969-84-3 (Z)-2-(5-acetyl-3-butyl-4-methylthiazol-2(3H)-ylidene)-1-(5-chloro-2-methoxyphenyl)ethanone 

Relevant academic research and scientific papers

Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes

Fosu, Hambira, and colleagues describe the direct C–H functionalization of medicinally relevant arenes or heteroarenes. This strategy is enabled by transient generation of reactive, non-symmetric iodanes from anions and PhI(OAc)2. The site-selective incorporation of Cl, Br, OMs, OTs, and OTf to complex molecules, including within medicines and natural products, can be conducted by the operationally simple procedure included herein. A computational model for predicting site selectivity is also included. The discovery of new medicines is a time- and labor-intensive process that frequently requires over a decade to complete. A major bottleneck is the synthesis of drug candidates, wherein each complex molecule must be prepared individually via a multi-step synthesis, frequently requiring a week of effort per molecule for thousands of candidates. As an alternate strategy, direct, post-synthetic functionalization of a lead candidate could enable this diversification in a single operation. In this article, we describe a new method for direct manipulation of drug-like molecules by incorporation of motifs with either known pharmaceutical value (halides) or that permit subsequent conversion (pseudo-halides) to medicinally relevant analogs. This user-friendly strategy is enabled by combining commercial iodine reagents with salts and acids. We expect this simple method for selective, post-synthetic incorporation of molecular diversity will streamline the discovery of new medicines. A strategy for C–H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C–H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.

Design, synthesis and biological evaluation of novel ring-opened cromakalim analogues with relaxant effects on vascular and respiratory smooth muscles and as stimulators of elastin synthesis

Two new series of ring-opened analogues of cromakalim bearing sulfonylurea moieties (series A: with N-unmethylated sulfonylureas, series B: with N-methylated sulfonylureas) were synthesized and tested as relaxants of vascular and respiratory smooth muscle

FLT3 RECEPTOR ANTAGONISTS

The invention pertains to novel FLT3receptor antagonists of general formula (1). The compounds are useful for the treatment or the prevention of pain disorders, cancer and autoimmune diseases.

Photolysis of α,β-Epoxyketones: A Green Synthesis of β-Hydroxyenones through Tandem H-Abstraction, Ring Cleavage and Isomerisation

The photochemical behavior of various substituted epoxycarbonyl compounds consisting of more than one possible photo-labile site (i.e. δ-hydrogen, β-hydrogen and epoxide ring) has been investigated. These compounds on photo-irradiation produced the β-hydr

Pyrazolyl-Based Carboxamides II

The invention relates to pyrazolyl-based carboxamide compounds useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.

PYRAZOLYL-BASED CARBOXAMIDES II AS CRAC CHANNEL INHIBITORS

The invention relates to pyrazolyl-based carboxamide compounds of formula (I) useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.

Chromenones as potent bradykinin B1 antagonists

A series of fused 6,6-bicyclic chromenones was investigated for activity against the bradykinin B1 receptor. SAR studies based on a pharmacophore model revealed compounds with high affinity for both human and rabbit B1. These compounds demonstrated favorable pharmacokinetic properties and 5-chlorochromenone 15 was efficacious in a carrageenan-induced mechanical hyperalgesia model for chronic pain.

COMPOUNDS, METHODS AND FORMULATIONS FOR THE ORAL DELIVERY OF A GLUCAGON LIKE PEPTIDE (GLP)-1 COMPOUND OR AN MELANOCORTIN 4 RECEPTOR (MC4) AGONIST PEPTIDE

The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.

Addition of Grignard reagents to aryl acid chlorides: An efficient synthesis of aryl ketones

(Chemical Equation Presented) Direct addition of Grignard reagents to acid chlorides in the presence of bis[2-(N,N-dimethylamino)ethyl] ether proceeds selectively to provide aryl ketones in high yields. A possible tridentate interaction between Grignard reagents and bis[2-(N,N-dimethylamino)ethyl] ether moderates the reactivity of Grignard reagents, preventing the newly formed ketones from nucleophilic addition by Grignard reagents.

Rate of Enolate Formation Is Not Very Sensitive to the Hydrogen Bonding Ability of Donors to Carboxyl Oxygen Lone Pair Acceptors; A Ramification of the Principle of Non-Perfect Synchronization for General-Base-Catalyzed Enolate Formation

Two series of structures (1 and 2) possessing intramolecular hydrogen bonds to the lone-pair electrons of carbonyl oxygens have been examined to reveal the influence of the pKa of the hydrogen-bond donor on the rate of general-base-catalyzed enolate formation. The geometry of the hydrogen bonds is well accepted to be appropriate for intramolecular hydrogen-bond formation. Yet, as revealed by Bronsted plots, both series show very little dependence of the rate of enolate formation on the hydrogen-bond donor ability. The intramolecular hydrogen bonds give rate enhancements only on the order of 10-100-fold, and corrected Bronsted α-values are slightly below 0.1. The results can be understood by interpreting them in light of the Principle of Non-Perfect Synchronization. The results are consistent with the proton transfer occurring through an asynchronous transition state with the developing negative charge localized on carbon. We postulate that catalysts of enolate formation will be most effective if the binding groups are focused on stabilizing negative charge that is forming on the enolate carbon rather than on the enolate oxygen.