142374-19-4

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-oxoethyl)piperidine-1-carboxylic acid, tert-butyl ester is used as a key intermediate for the synthesis of various pharmaceutical compounds, such as Pim-1 inhibitors. Pim-1 inhibitors are a class of drugs that target the Pim-1 protein, which is involved in cell proliferation and survival, and has been implicated in various cancers.
Used in the Synthesis of GPR119 Agonists:
4-(2-oxoethyl)piperidine-1-carboxylic acid, tert-butyl ester is also used as a reactant in the synthesis of selective GPR119 agonists. GPR119 is a G-protein coupled receptor that plays a role in glucose homeostasis and has been identified as a potential target for the treatment of type II diabetes.
Used in Organic Synthesis:
4-(2-oxoethyl)piperidine-1-carboxylic acid,tert-butyl ester serves as a versatile reactant for various organic synthesis processes, including α-arylation, enantioselective α-benzylation, and enantioselective α-trifluoromethylation of aldehydes. These reactions are important for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C12H21NO3/c1-12(2,3)16-11(15)13-7-4-10(5-8-13)6-9-14/h9-10H,4-8H2,1-3H3

Upstream product

• 89151-44-0 4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester 
• 135716-09-5 tert-butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate 
• 6622-91-9 2-(pyridine-4-yl)acetic acid hydrochloride 
• 60-29-7 diethyl ether 
• 502609-58-7 tert-butyl 4-(2-oxoethylidene)piperidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 622-26-4 4-(2-Hydroxyethyl)piperidine 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 137076-22-3 tert butyl 4-formylpiperidine-1-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 79-37-8 oxalyl dichloride 
• 28356-58-3 pyridine-4-acetic acid 
• 51052-78-9 4-piperidinylacetic acid 
• 157688-46-5 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid 

Downstream Products

• 142355-80-4 methyl 4-piperidin-4-yl>but-2-enoate 
• 301185-40-0 1-(t-butoxycarbonyl)-4-(3,3-dibromoprop-2-en-1-yl)piperidine 
• 206446-47-1 4-(prop-2-en-1-yl)-1-t-butoxycarbonylpiperidine 
• 817636-74-1 4-[4-(4-methylbenzenesulfonyl)-4,5-dihydrooxazol-5-ylmethyl]piperidine-1-carboxylic acid tert-butyl ester 
• 871675-56-8 4-(3-benzyloxycarbonylamino-3-methoxycarbonyl-allyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 339525-17-6 1-(o-iodobenzoyl)-4-[3-(trimethylsilyl)prop-2-ynyl]piperidine 
• 339525-21-2 1-(o-iodobenzoyl)-4-[4-(trimethylsilyl)but-3-ynyl]piperidine 
• 146144-48-1 N-<<3(R)-(-)-<2-(piperidin-4-yl)ethyl>-2-oxopiperidin-1-yl>acetyl>-3(R)-methyl-β-alanine 
• 896103-62-1 tert-butyl 4-(2-(methylamino)ethyl)piperidine-1-carboxylate 
• 301221-63-6 tert-butyl 4-(1-bromo-2-oxoethyl)piperidine-1-carboxylate 
• 912447-66-6 tert-butyl 4-[2-hydroxy-2-(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate 

Relevant academic research and scientific papers

1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists: Modifications of the arylpropylpiperidine side chains

The 4-(3-phenylprop-1-yl)piperidine moiety of the 1,3,4-trisubstituted pyrrolidine CCR5 antagonist 1 was modified with electron deficient aromatics as well as replacement of the benzylic methylene with sulfones, gem-difluoromethylenes and alcohols in an effort to balance the antiviral potency with reasonable pharmacokinetics.

N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation

The site-specific oxidation of strong C(sp3)-H bonds is of uncontested utility in organic synthesis. From simplifying access to metabolites and late-stage diversification of lead compounds to truncating retrosynthetic plans, there is a growing need for new reagents and methods for achieving such a transformation in both academic and industrial circles. One main drawback of current chemical reagents is the lack of diversity with regard to structure and reactivity that prevents a combinatorial approach for rapid screening to be employed. In that regard, directed evolution still holds the greatest promise for achieving complex C-H oxidations in a variety of complex settings. Herein we present a rationally designed platform that provides a step toward this challenge using N-ammonium ylides as electrochemically driven oxidants for site-specific, chemoselective C(sp3)-H oxidation. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors.

Discovery of a Novel, Highly Potent, and Selective Thieno[3,2- d]pyrimidinone-Based Cdc7 Inhibitor with a Quinuclidine Moiety (TAK-931) as an Orally Active Investigational Antitumor Agent

In our pursuit of developing a novel, potent, and selective cell division cycle 7 (Cdc7) inhibitor, we optimized the previously reported thieno[3,2-d]pyrimidinone analogue I showing time-dependent Cdc7 kinase inhibition and slow dissociation kinetics. These medicinal chemistry efforts led to the identification of compound 3d, which exhibited potent cellular activity, excellent kinase selectivity, and antitumor efficacy in a COLO205 xenograft mouse model. However, the issue of formaldehyde adduct formation emerged during a detailed study of 3d, which was deemed an obstacle to further development. A structure-based approach to circumvent the adduct formation culminated in the discovery of compound 11b (TAK-931) possessing a quinuclidine moiety as a preclinical candidate. In this paper, the design, synthesis, and biological evaluation of this series of compounds will be presented.

Exploiting Synergistic Catalysis for an Ambient Temperature Photocycloaddition to Pyrazoles

Sydnone-based cycloaddition reactions are a versatile platform for pyrazole synthesis, however they operate under harsh conditions (high temperature and long reaction times). Herein we report a strategy that addresses this limitation utilizing the synergistic combination of organocatalysis and visible-light photocatalysis. This new approach proceeds under ambient conditions and with excellent levels of regiocontrol. Mechanistic studies suggest that photoactivation of sydnones, rather than enamines, is key to the successful implementation of this process.

6-bromo-3-(piperidine-4-yl)imidazo[1,2-a]pyridine preparation method

The invention relates to a 6-bromo-3-(piperidine-4-yl)imidazo[1,2-a]pyridine preparation method. A purpose of the present invention is mainly to solve the technical problem that no suitable industrialsynthesis method exists in the prior art. According to the technical scheme, the method comprises five steps, and comprises: generating a compound 2 from a compound 1 and Boc2O in chloroform under the action of triethylamine; adding dichloromethane, oxalyl chloride and dimethyl sulfoxide into the compound 2, and oxidizing to obtain a compound 3; carrying out a reaction on the compound 3 and a bromination reagent phenyltrimethylammonium tribromide (PTAB) in tetrahydrofuran to obtain a compound 4; carrying out a reaction on the compound 4 and 2-amino-5-bromopyridine in ethyl alcohol to obtain acompound 5; and finally obtaining a compound 6 from the compound 5 under the action of ethyl acetate hydrochloride. According to the present invention, the obtained compound can be used as the intermediate or product for synthesis of a plurality of drugs.

OXOPIPERAZINE DERIVATIVES

The present invention relates to novel compounds of formula (I) or formula (Ia) pharmaceutically-acceptable salts, hydrates, solvates, or stereoisomers thereof, and pharmaceutical compositions of these compounds which are useful for preventive and therapeutic use in human and veterinary medicine.

N-ARYL AND N-HETEROARYL PIPERIDINE DERIVATIVES AS LIVER X RECEPTOR β AGONISTS, COMPOSITIONS, AND THEIR USE

Provided herein are certain substituted N-aryl and N-heteroaryl piperidine compounds of the formula (I) and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, L, R4, L1, Q, R5 and R 6 are as defined. The said novel compounds, and pharmaceutically acceptable compositions comprising a compound thereof, may be useful as Liver X-β receptor(LXRβ) agonists, and may be useful for treating or preventing pathologies related thereto. Such pathologies include, but are not limited to, inflammatory disease and diseases characterized by defects in cholesterol and lipid metabolism, such as Alzheimer's disease.

HETEROAROMATIC ELECTROPHILES AND METHODS OF USING THEREOF

Disclosed herein are compounds, compositions, and methods for reactivating or realkylating aged acetylcholinesterase inhibited by or conjugated to the organophosphorus compound. The organophosphorus compound can be a nerve agent. The acetylcholinesterase can be in the central nerve system (CNS) and/or the peripheral nervous system (PNS) of a subject. Accordingly, methods for ameliorating, diminishing, reversing, treating or preventing the toxic effects of an organophosphorus compound in a subject are provided herein. Methods for prophylactic or therapeutic treatment of exposure to an organophosphorus nerve agent are also provided.

NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3)?H Alkylation of Alkenes

The terminal-selective, remote C(sp3)?H alkylation of alkenes was achieved by a relay process combining NiH-catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp3)?C(sp3) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated by the large-scale and regioconvergent alkylation of isomeric mixtures of olefins at low catalyst loadings.

Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols

Nature routinely engages alcohols as leaving groups, as DNA biosynthesis relies on the removal of water from ribonucleoside diphosphates by a radical-mediated "spin-center shift" (SCS) mechanism. Alcohols, however, remain underused as alkylating agents in synthetic chemistry due to their low reactivity in two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes using alcohols as alkylating agents based on the mechanistic principle of spin-center shift. This strategy harnesses the dual activation modes of photoredox and organocatalysis, engaging the alcohol by SCS and capturing the resulting benzylic radical with a catalytically generated enamine. Mechanistic studies provide evidence for SCS as a key elementary step, identify the origins of competing reactions, and enable improvements in chemoselectivity by rational photocatalyst design.