86770-31-2

Basic information

• Product Name: 3,5-Dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester
• Synonyms: 3,5-dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester;3,5-DIMETHYLPYRROLE-2,4-DICARBOXYLIC ACID 4-ETHYL ESTER-2-T-BUTYL ESTER;3,5-DIMETHYLPYRROLE-2,4-DICARBOXYLIC ACID 4-ETHYL ESTER-2-TERT-BUTYL ESTER;3,5-DIMETHYL-1H-PYRROLE-2,4-DICARBOXYLIC ACID-2-BUTYL-4-ETHYL ESTER;3,5-DIMETHYL-1H-PYRROLE-2,4-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER 4-ETHYL ESTER;2-TERT-BUTYL 4-ETHYL 3,5-DIMETHYL-1H-PYRROLE-2,4-DICARBOXYLATE;SALOR-INT L157929-1EA;2-tert-Butyl 4-ethyl 3,5-dimethylpyrrole-2,4-dicarboxylate
• CAS NO: 86770-31-2
• Molecular Formula: C₁₄H₂₁NO₄
• Molecular Weight: 267.32
• EINECS: 1806241-263-5
• Product Categories: HANTZSCH;Pharmaceutial intermediates;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Organic acids;API intermediates;Intermediate of sunitinib malate
• Mol File: 86770-31-2.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 386.8 °C at 760 mmHg
• Flash Point: 187.8 °C
• Appearance: /
• Density: 1.103 g/cm³
• Vapor Pressure: 3.44E-06mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: 2-8°C
• PKA: 14.56±0.50(Predicted)
• CAS DataBase Reference: 3,5-Dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester(86770-31-2)
• EPA Substance Registry System: 3,5-Dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester(86770-31-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 86770-31-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H21NO4/c1-7-18-12(16)10-8(2)11(15-9(10)3)13(17)19-14(4,5)6/h15H,7H2,1-6H3

Upstream product

• 1694-31-1 tert-butyl acetoacetate 
• 79232-64-7 (Z)-2-hydroxyimino-3-oxo-butyric acid tert-butyl ester 
• 141-97-9 ethyl acetoacetate 
• 1312786-80-3 tert-butyl (E)-2-(hydroxyimino)-3-oxobutanoate 
• 14352-65-9 t-butyl 2-hydroxyimino-3-oxobutanoate 

Downstream Products

• 2199-59-9 ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate 
• 341031-54-7 sunitinib malate 

Relevant articles and documents

Antimicrobial and antiproliferative study of chalcone clubbed 2,4-dimethylpyrrole-3-carboxamide derivatives: Synthesis and in vitro evaluation

The presented study explores the anticancer potency of a novel series of chalcone clubbed 2,4-dimethyl-1H-pyrrole-3-carboxamide derivatives. In vitro antimicrobial screening concluded that five compounds are potential against Candida albicans having inhibition of growth in the range of 46.38%–73.05% against at the concentration of 32 μg/mL. The antiproliferative screening against 60 cancer cell lines revealed that seven compounds have great potential against the various types of cancer cell lines with inhibition of growth in the range of 41%–71%. The structure–activity relationship study concluded that the hydrazide bond is more significant than the carboxamide bond. In silico study of highly potential derivatives obeys each parameter of Lipinski rule of five and qualified drug-likeness behavior. The presented pyrrole-chalcone template delivered various candidates as anticancer agents, and those could be a potential scaffold to develop the new anticancer drug.

Low-cost clean method for preparing 2,4-dimethyl pyrrole-3,5-dicarboxylate

The invention discloses a low-cost clean method for preparing 2,4-dimethyl pyrrole-3,5-dicarboxylate. The method comprises the following steps: mixing ethyl acetoacetate or tert-butyl acetoacetate with glacial acetic acid, slowly introducing inert gas into the mixed solution for 30 minutes, then introducing a nitrosation reagent nitric oxide gas at the flow rate of 0.5-1mL/min, conducting reacting at room temperature for 10 hours, controlling the temperature of the reaction solution to be 40 DEG C or lower, adding zinc powder in batches, dropwise adding ethyl acetoacetate at the same time, conducting reacting at 95 DEG C for 4 hours, conducting cooling, adding a reaction solution into ice water, conducting filtering, recrystallizing a filter cake with ethanol to obtain white ethyl 2,4-dimethyl pyrrole-3,5-dicarboxylate, and concentrating a filtrate to recover zinc acetate and acetic acid so as to realize the cleanness of the preparation process.

Development of a novel conjugatable sunitinib analogue validated through in vitro and in vivo preclinical settings

Sunitinib is an oral FDA/EMEA approved multi-targeted tyrosine kinase inhibitor. It possesses anti-angiogenic and antitumor activity against a variety of advanced solid tumors. However, its chemical core does not allow a potential linkage to tumor-homing elements that could eventually enhance its potency. Therefore, a novel linkable sunitinib derivative, designated SB1, was rationally designed and synthesized. The pharmaceutical profile of SB1 was explored both in vitro and in vivo. Mass spectrometry and NMR spectroscopy were utilized for characterization, while MTT assays and LC-MS/MS validated protocols were used to explore its antiproliferative effect and stability, respectively. Cytotoxicity evaluation in three glioma cells showed that SB1 preserved the antiproliferative effect of sunitinib. SB1 was stable in vitro after 24 h incubation in mouse plasma, while both agents exhibited bioequivalent pharmacokinetic characteristics after i.v. administration in Balb/c mice. To evaluate the levels of SB1 in mouse plasma, a novel analytical method was developed and validated in accordance to the US FDA and the EU EMA guidelines. We formulated a novel linkable sunitinib analog exhibiting similar antiproliferative and apoptotic properties with native sunitinib in glioma cell lines. Both SB1 and native sunitinib showed identical in vitro stability in mouse plasma and pharmacokinetics after i.v. administration in Balb/c mice.