107750-90-3

Upstream product

• 76513-69-4 (2-trimethylethylsilylethoxy)methyl chloride 
• 864825-98-9 5-phenyl-1-(2-(trimethylsilanyl)-ethoxymethyl)-1H-imidazole 
• 670-95-1 4-Phenylimidazole 

Downstream Products

• 107750-96-9 Cyclohexyl-(4-phenyl-1H-imidazol-2-yl)-methanol 
• 107750-91-4 C₁₅H₂₁⁽²⁾HN₂OSi 
• 107750-94-7 Cyclohexyl-[4-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanol 
• 107750-93-6 (E)-3-Phenyl-1-[4-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-prop-2-en-1-ol 
• 405174-04-1 4-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehyde 
• 864825-43-4 5-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde 
• 1195985-32-0 (R)-1-phenyl-N-((4-phenyl-1H-imidazol-2-yl)methyl)ethanamine 
• 1195985-47-7 (R)-1-phenyl-N-((4-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)methyl)ethanamine 

Relevant academic research and scientific papers

C-H bonds as ubiquitous functionality: A general approach to complex arylated imidazoles via regioselective sequential arylation of all three C-H bonds and regioselective n -alkylation enabled by SEM-group transposition

(Figure presented) Imidazoles are an important group of the azole family of heterocycles frequently found in pharmaceuticals, drug candidates, ligands for transition metal catalysts, and other molecular functional materials. Owing to their wide application in academia and industry, new methods and strategies for the generation of functionalized imidazole derivatives are in demand. We here describe a general and comprehensive approach for the synthesis of complex aryl imidazoles, where all three C-H bonds of the imidazole core can be arylated in a regioselective and sequential manner. We report new catalytic methods for selective C5- and C2-arylation of SEM-imidazoles and provide a mechanistic hypothesis for the observed positional selectivity based on electronic properties of C-H bonds and the heterocyclic ring. Importantly, aryl bromides and low-cost aryl chlorides can be used as arene donors under practical laboratory conditions. To circumvent the low reactivity of the C-4 position, we developed the SEM-switch that transfers the SEM-group from N-1 to N-3 nitrogen and thus enables preparation of 4-arylimidazoles and sequential C4-C5-arylation of the imidazole core. Furthermore, selective N3-alkylation followed by the SEM-group deprotection (trans-N-alkylation) allows for regioselective N-alkylation of complex imidazoles. The sequential C-arylation enabled by the SEM-switch allowed us to produce a variety of mono-, di-, and triarylimidazoles using diverse bromo- and chloroarenes. Using our approach, the synthesis of individual compounds or libraries of analogues can begin from either the parent imidazole or a substituted imidazole, providing rapid access to complex imidazole structures.

Discovery and optimization of substituted 1-(1-phenyl-1H-pyrazol-3-yl) methanamines as potent and efficacious type II calcimimetics

Our efforts to discover potent, orally bioavailable type II calcimimetic agents for the treatment of secondary hyperparathyroidism focused on the development of ring constrained analogues of the known calcimimetic R-568. The structure-activity relationships of various substituted heterocycles and their effects on the human calcium-sensing receptor are discussed. Pyrazole 15 was shown to be efficacious in a rat in vivo pharmacodynamic model.

Chemokine receptor binding heterocyclic compounds

This invention relates to a novel class of heterocyclic compounds that bind chemokine receptors, inhibiting the binding of their natural ligands thereby. These compounds result in protective effects against infection by HIV through binding to chemokine receptors, including CXCR4 and CCR5, thus inhibiting the subsequent binding by these chemokines. The present invention provides a compound of Formula I wherein, W is a nitrogen atom and Y is absent or, W is a carbon atom and Y═H; R1to R7may be the same or different and are independently selected from hydrogen or straight, branched or cyclic C1-6alkyl; R8is a substituted heterocyclic group or a substituted aromatic group Ar is an aromatic or heteroaromatic ring each optionally substituted at single or multiple, non-linking positions with electron-donating or withdrawing groups; n and n′ are independently, 0-2; X is a group of the formula: Wherein, Ring A is an optionally substituted, saturated or unsaturated 5 or 6-membered ring, and P is an optionally substituted carbon atom, an optionally substituted nitrogen atom, sulfur or oxygen atom. Ring B is an optionally substituted 5 to 7-membered ring. Ring A and Ring B in the above formula can be connected to the group W from any position via the group V, wherein V is a chemical bond, a (CH2)n″group (where n″=0-2) or a C═O group. Z is, (1) a hydrogen atom, (2) an optionally substituted C1-6alkyl group, (3) a C0-6alkyl group substituted with an optionally substituted aromatic or heterocyclic group, (4) an optionally substituted C0-6alkylamino or C3-7cycloalkylamino group, (5) an optionally substituted carbonyl group or sulfonyl. These compounds further include any pharmaceutically acceptable acid addition salts and metal complexes thereof and any stereoisomeric forms and mixtures of stereoisomeric forms thereof.

PROTECTION OF IMIDAZOLES AS THEIR β-TRIMETHYLSILYLETHOXYMETHYL (SEM) DERIVATIVES

Monocyclic 4(5)-substituted imidazoles react with SEM-Cl to afford the corresponding N-SEM derivatives.These aminals readily metalate at C-2 with n-BuLi in THF at -78 deg C and react with various electrophiles.Deprotection may be achieved with either n-Bu