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
• Article Data: 6

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

• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 6165-69-1 Thien-3-ylboronic acid 
• 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 
• 872-31-1 3-Bromothiophene 

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.

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 In this study we report JDTic analogs 2, 3a–b, 4a–b, and 5, where the 3-hydroxyphenyl ring has been replaced by a 2-, 3-, or 4-pyridyl or 3-thienyl group and do not have the 3-methyl or 3,4-dimethyl groups, remain potent and selective KOR antagonists.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.

HETEROARYLPIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present invention is directed to compounds of the formula (I): (wherein R>12345610 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.