690261-78-0

Basic information

• Product Name: 4-(3-Thienyl)-1-piperidinecarboxylic acid 1,1-dimethylethylester
• Synonyms: 4-(3-Thienyl)-1-piperidinecarboxylic acid 1,1-dimethylethylester;4-(3-Thienyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester
• CAS NO: 690261-78-0
• Molecular Formula: C14H21NO2S
• Molecular Weight: 267.391
• Mol File: 690261-78-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(3-Thienyl)-1-piperidinecarboxylic acid 1,1-dimethylethylester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Thienyl)-1-piperidinecarboxylic acid 1,1-dimethylethylester(690261-78-0)
• EPA Substance Registry System: 4-(3-Thienyl)-1-piperidinecarboxylic acid 1,1-dimethylethylester(690261-78-0)

Safety Data

• Hazardous Substances Data: 690261-78-0(Hazardous Substances Data)

Upstream product

• 872-31-1 3-Bromothiophene 
• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 6165-69-1 Thien-3-ylboronic acid 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 690261-77-9 tert-butyl 4-thiophen-3-yl-3,6-dihydropyridine-1(2H)-carboxylate 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Iron-Catalyzed C(sp 2)-C(sp 3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides

An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C-C bond-forming reactions.

Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids

A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N-hydroxy-tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl2?6 H2O—$9.5 mol?1, Et3N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.

Design, synthesis, and pharmacological evaluation of JDTic analogs to examine the significance of replacement of the 3-hydroxyphenyl group with pyridine or thiophene bioisosteres

The potent and selective KOR antagonist JDTic was derived from the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine class of pure opioid antagonists. In previous studies we reported that compounds that did not have a hydroxyl on the 3-hydroxyphenyl group and did not have methyl groups at the 3- and 4-position of the piperidine ring were still potent and selective KOR antagonists. In this study we report JDTic analogs 2, 3a–b, 4a–b, and 5, where the 3-hydroxyphenyl ring has been replaced by a 2-, 3-, or 4-pyridyl or 3-thienyl group and do not have the 3-methyl or 3,4-dimethyl groups, remain potent and selective KOR antagonists. Of these, (3R)-7-hydroxy-N-(1S)-2-methyl-[4-methyl-4-pyridine-3-yl-carboxamide (3b) had the best overall binding potency and selectivity in a [35S]GTPγS functional assay, with a Ke?=?0.18?nM at the KOR and 273- and 16,700-fold selectivity for the KOR relative to the MOR and DOR, respectively. Calculated physiochemical properties for 3b suggest that it will cross the blood–brain barrier.

Cross-couplings of alkyl halides with heteroaromatic halides, in water at room temperature

Zn-mediated, Pd-catalyzed cross-coupling reactions between heteroaromatic and alkyl halides can be done at room temperature in pure water using a commercially available Pd catalyst and PTS, a nanomicelle-forming amphiphile. Notably, zinc metal inserts selectively into a carbon sp3-halide bond, while palladium adds oxidatively to a carbon sp2-bond.

HETEROARYLPIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

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GAMMA-AMINOAMIDE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present invention is directed to compounds of the formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R11, R12, W, X, and n are defined herein, which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.