1187595-88-5

Basic information

• Product Name: 4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
• Synonyms: 4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
• CAS NO: 1187595-88-5
• Molecular Formula: C19H29N5O2Si
• Molecular Weight: 387.55136
• Mol File: 1187595-88-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 509.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• PKA: 3.75±0.30(Predicted)
• CAS DataBase Reference: 4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine(1187595-88-5)
• EPA Substance Registry System: 4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine(1187595-88-5)

Safety Data

• Hazardous Substances Data: 1187595-88-5(Hazardous Substances Data)

Usage

General Description

4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine is a complex organic compound featuring various functional groups. These groups include a pyrazole, a pyrimidine and a pyrrole ring, all common structures in biochemistry and medicinal chemistry. The 4-pyrazolyl and 7-pyrrolopyrimidine constitute a hydride structure - a common component in many pharmaceutical drugs. The trimethylsilyl (TMS) ether group contributes to its chemical stability, while the ethoxyethyl group could increase its lipid solubility, potentially favoring its passage through cell membranes. Although specific uses of this chemical are not detailed, its presence of several pharmacophoric moieties suggests its potential use in drug development.

Upstream product

• 76513-69-4 (2-trimethylethylsilylethoxy)methyl chloride 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 941685-26-3 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1029716-44-6 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole 

Downstream Products

• 941685-27-4 4-(1H-pyrazol-4-yl)-7-((2-trimethylsilanylethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1334298-90-6 2-(1-{1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl}-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile 
• 1334302-63-4 2-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)azetidin-3-yl)acetonitrile adipate 

Relevant articles and documents

Pyrrole pyrimidine five-membered nitrogen-heterocyclic derivative and application thereof

The invention relates to a novel JAK (Janus kinase) inhibitor, namely a pyrrole pyrimidine five-membered nitrogen-heterocyclic derivative, and application of the pyrrole pyrimidine five-membered nitrogen-heterocyclic derivative in preparation of a medicine for preventing and/or treating JAK function-related adaptation diseases. The pyrrole pyrimidine five-membered nitrogen-heterocyclic derivative disclosed by the invention is an ideal efficient JAK inhibitor, and can be used for treating or preventing diseases such as rheumatoid arthritis, polycythemia vera, psoriasis, primary thrombocythemia and myelofibrosis.

PROCESSES AND INTERMEDIATES FOR MAKING A JAK INHIBITOR

This invention relates to processes and intermediates for making {1-{1-[3-fluoro-2-(trifluoromethyl)isonicotinoyl]piperidin-4-yl}-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile, useful in the treatment of diseases related to the activity of Janus kinases (JAK) including inflammatory disorders, autoimmune disorders, cancer, and other diseases.

Enantioselective synthesis of janus kinase inhibitor INCB018424 via an organocatalytic aza-michael reaction

An enantioselective synthesis of INCB018424 via organocatalytic asymmetric aza-Michael addition of pyrazoles (16 or 20) to (E)-3- cyclopentylacrylaldehyde (23) using diarylprolinol silyl ether as the catalyst was developed. Michael adducts (R)-24 and (R)-27 were isolated in good yield and high ee and were readily converted to INCB018424.