2971-79-1

Basic information

• Product Name: Methyl isonipecotate
• Synonyms: METHYL PIPERIDINE-4-CARBOXYLATE;METHYL ISONIPECOTATE;METHYL 4-PIPERIDINECARBOXYLATE;ISONIPECOTIC ACID, METHYL AND ETHYL ESTERS;4-PIPERDINECARBOXYLIC ACID, METHYL ESTER;4-PIPERIDINECARBOXYLIC ACID METHYL ESTER;Isonipecotic acid methyl ester;Methyl Piperidinecarboxylate
• CAS NO: 2971-79-1
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18
• EINECS: 1592732-453-0
• Product Categories: pharmacetical;Piperidine;Heterocycles;Intermediates;Miscellaneous Reagents
• Mol File: 2971-79-1.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 85-90°C
• Flash Point: 192°F
• Appearance: Colorless to yellow/Liquid
• Density: 1.06
• Vapor Pressure: 0.457mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform
• PKA: 9.78±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: Methyl isonipecotate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl isonipecotate(2971-79-1)
• EPA Substance Registry System: Methyl isonipecotate(2971-79-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3267
• WGK Germany: 3
• Hazardous Substances Data: 2971-79-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl isonipecotate is used as a reactant for the synthesis of antitubercular agents, aminopyrazine inhibitors, orally available naphthyridine protein kinase D inhibitors, and a scalable catalyst from asymmetric hydrogenation of sterically demanding aryl enamide. It plays a crucial role in the development of new drugs for the treatment of tuberculosis, neurological disorders, and other diseases.
Used in Chemical Synthesis:
Methyl isonipecotate is used as a reagent in the organic synthesis of neurochemicals, antibacterials, and other biologically active compounds. Its versatile chemical properties make it a valuable component in the creation of various pharmaceuticals and chemicals with potential therapeutic applications.
Used in Enzyme Inhibition Research:
Methyl isonipecotate may be used for the synthesis of a series of potent non-urea soluble epoxide hydrolase (sEH) inhibitors via high throughput screens. These inhibitors can be valuable tools in studying the role of sEH in various biological processes and may lead to the development of new treatments for diseases associated with sEH dysregulation.

InChI:InChI=1/C7H13NO2/c1-10-7(9)6-2-4-8-5-3-6/h6,8H,2-5H2,1H3

Upstream product

• 498-94-2 isonipecotic acid 
• 128094-80-4 4-bromo-2-(2-bromoethyl)butanoic acid 
• 857778-39-3 4-bromo-2-(2-bromo-ethyl)-butyric acid ethyl ester 
• 1083159-12-9 O₂-(2,4-dinitrophenyl) 1-[(4-methoxycarbonyl)piperidin-1-yl]diazen-1-ium-1,2-diolate 
• 1262670-73-4 N-tritylisonipecotic acid methyl ester 
• 55-22-1 pyridine-4-carboxylic acid 
• 67-56-1 methanol 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 

Downstream Products

• 1690-75-1 1-methyl-piperidine-4-carboxylic acid methyl ester 
• 126291-66-5 1-acetyl-piperidine-4-carboxylic acid methyl ester 
• 10315-06-7 1-benzylpiperidine-4-carboxylic acid methyl ester 
• 868854-95-9 1-(2-methoxy-phenyl)-piperidine-4-carboxylic acid methyl ester 
• 138163-07-2 piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-methyl ester 
• 960391-27-9 methyl 1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}carbonyl)piperidine-4-carboxylate 
• 922516-12-9 methyl 1-[(2,5-dimethylphenyl)acetyl]-4-piperidine-carboxylate 
• 1004528-08-8 methyl 1-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-4-carboxylate 
• 529509-43-1 1-{4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-piperidine-4-carboxylic acid 
• 529509-27-1 1-{4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-piperidine-4-carboxylic acid methyl ester 

Relevant articles and documents

The face selectivity of 1,3-dipolar cycloaddition reactions of 4-butyloxycarbonyl-3,4,5,6-tetrahydropyridine 1-oxide

A study of the stereo- and face selectivity of the cycloaddition reactions of a series of mono- and disubstituted alkenes with 4-butyloxycarbonyl-3,4,5,6-tetrahydropyridine 1-oxide has been carried out. Rate constants for the cycloaddition of the nitrone

Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture

The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.

Design, synthesis and anticancer activities of novel dual poly(ADP-ribose) polymerase-1/histone deacetylase-1 inhibitors

Currently, synergistic inhibition of poly(ADP-ribose) polymerase-1 (PARP-1) and histone deacetylases (HDACs) has been a potential effective strategy for cancer treatment. Herein, by combining critical pharmacophores in approved drugs olaparib and chidamid

Design and Synthesis of 56 Shape-Diverse 3D Fragments

Fragment-based drug discovery is now widely adopted for lead generation in the pharmaceutical industry. However, fragment screening collections are often predominantly populated with flat, 2D molecules. Herein, we describe a workflow for the design and synthesis of 56 3D disubstituted pyrrolidine and piperidine fragments that occupy under-represented areas of fragment space (as demonstrated by a principal moments of inertia (PMI) analysis). A key, and unique, underpinning design feature of this fragment collection is that assessment of fragment shape and conformational diversity (by considering conformations up to 1.5 kcal mol?1 above the energy of the global minimum energy conformer) is carried out prior to synthesis and is also used to select targets for synthesis. The 3D fragments were designed to contain suitable synthetic handles for future fragment elaboration. Finally, by comparing our 3D fragments with six commercial libraries, it is clear that our collection has high three-dimensionality and shape diversity.

INHIBITORS OF RENAL OUTER MEDULLARY POTASSIUM CHANNEL

Compounds of Formula I and the pharmaceutically acceptable salts thereof are provided as inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula I (I) and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula (I) and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir11) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

Ceric ammonium nitrate-mediated detritylation of tritylated amines

Efficient deprotection of tritylated amines to the corresponding amines mediated by 20 mol % ceric ammonium nitrate [Ce(NH4) 2(NO3)6, CAN], 10 equiv of acetic acid and 15 equiv of water in dichloromethane is presented. This method equally worked well in the case of morpholino nucleosides.