325486-45-1

Basic information

• Product Name: 4-OXO-3,4-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: 4-OXO-3,4-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;TERT-BUTYL 4-OXO-3,4-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE;1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-4-oxo-, 1,1-diMethylethyl ester;4-Oxo-1,2,3,4-tetrahydropyridine, N-BOC protected;tert-Butyl 3,4-dihydro-4-oxopyridine-1(2H)-carboxylate, 1-(tert-Butoxycarbonyl)-4-oxo-1,2,3,4-tetrahydropyridine;1-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydropyridin-4-one;tert-Butyl 1,4,5,6-tetrahydro-4-oxopyridine-1-carboxylate;tert-butyl 4-oxo-2,3-dihydropyridine-1-carboxylate
• CAS NO: 325486-45-1
• Molecular Formula: C₁₀H₁₅NO₃
• Molecular Weight: 197.23
• Product Categories: pharmacetical
• Mol File: 325486-45-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 53-54℃
• Boiling Point: 286.3±33.0 °C(Predicted)
• Appearance: /
• Density: 1.130±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -4.15±0.20(Predicted)
• CAS DataBase Reference: 4-OXO-3,4-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-OXO-3,4-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(325486-45-1)
• EPA Substance Registry System: 4-OXO-3,4-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(325486-45-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36-52
• Safety Statements: 26
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 325486-45-1(Hazardous Substances Data)

Usage

General Description

4-OXO-3,4-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is a chemical compound with a complex structure. It belongs to the chemical class of pyridines, specifically a dihydropyridine, which is a heterocyclic compound. These classes of compounds are often used to generate various pharmaceutical formulations. The presence of ester functionality, in this case, a tert-butyl ester, often makes this compound a useful synthetic intermediate in organic chemistry reactions. Its properties like solubility, boiling point, melting point, etc., may vary depending upon the specific conditions and external environment.

Upstream product

• 620-08-6 4-methoxypyridine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 865-47-4 potassium tert-butylate 
• 1885-14-9 phenyl chloroformate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 841286-80-4 (±)-tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate 
• 131667-57-7 tert-butyl 1,2,3,4-tetrahydro-1-pyridinecarboxylate 
• 24681-60-5 1,2,3,4-tetrahydro-4-oxopyridine 
• 121507-66-2 (+/-)-1-((phenyloxy)carbonyl)-1,2,3,4-tetrahydro-4-pyridone 
• 188869-05-8 tert-butyl 3-bromo-4-oxo-piperidine-1-carboxylate 

Downstream Products

• 790667-43-5 (2R)-2-methyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 1284129-42-5 tert-butyl 4-oxo-6-phenyl-3,4-dihydropyridine-1(2H)-carboxylate 
• 1365918-68-8 (E)-tert-butyl 4-oxo-2-styrylpiperidine-1-carboxylate 

Relevant articles and documents

Catalytic asymmetric synthesis of the alkaloid (+)-myrtine

A new protocol for the asymmetric synthesis of trans-2,6-disubstituted-4- piperidones has been developed using a catalytic enantioselective conjugate addition reaction in combination with a diastereoselective lithiation- substitution sequence; an efficient synthesis of (+)-myrtine has been achieved via this route.

Preparation method of tert-butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate

The invention discloses a preparation method of tert-butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate, which comprises the steps of dissolving tert-butyl 3-bromo-4-oxopiperidine-1-carboxylate in a solvent, adding alkali, and reacting to obtain tert-butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate. According to the preparation method of tert-butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate provided by the invention, the used raw materials such as tert-butyl 3-bromo-4-oxopiperidine-1-carboxylate, lithium bromide and lithium carbonate are wide in source, cheap and easily available, and tert-butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate can be quickly and efficiently obtained by only one-step reaction.

Design, Synthesis, and Pharmacological Characterization of a Neutral, Non-Prodrug Thrombin Inhibitor with Good Oral Pharmacokinetics

Despite extensive research on small molecule thrombin inhibitors for oral application in the past decades, only a single double prodrug with very modest oral bioavailability has reached human therapy as a marketed drug. We have undertaken major efforts to identify neutral, non-prodrug inhibitors. Using a holistic analysis of all available internal data, we were able to build computational models and apply these for the selection of a lead series with the highest possibility of achieving oral bioavailability. In our design, we relied on protein structure knowledge to address potency and identified a small window of favorable physicochemical properties to balance absorption and metabolic stability. Protein structure information on the pregnane X receptor helped in overcoming a persistent cytochrome P450 3A4 induction problem. The selected compound series was optimized to a highly potent, neutral, non-prodrug thrombin inhibitor by designing, synthesizing, and testing derivatives. The resulting optimized compound, BAY1217224, has reached first clinical trials, which have confirmed the desired pharmacokinetic properties.