1817630-30-0

Basic information

• Product Name: (3R,4R,5S)-4-ethyl-3-fluoro-5-(hydroxymethyl)pyrrolidin-2-one
• CAS NO: 1817630-30-0
• Molecular Weight: 161.176
• Mol File: 1817630-30-0.mol

Chemical Properties

• CAS DataBase Reference: (3R,4R,5S)-4-ethyl-3-fluoro-5-(hydroxymethyl)pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5S)-4-ethyl-3-fluoro-5-(hydroxymethyl)pyrrolidin-2-one(1817630-30-0)
• EPA Substance Registry System: (3R,4R,5S)-4-ethyl-3-fluoro-5-(hydroxymethyl)pyrrolidin-2-one(1817630-30-0)

Safety Data

• Hazardous Substances Data: 1817630-30-0(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(3R,4R,5S)-4-ethyl-3-fluoro-5-(hydroxymethyl)pyrrolidin-2-one is used as a chiral building block for the synthesis of pharmaceutical compounds, leveraging its unique stereochemistry and functional groups to create novel drugs with potential therapeutic benefits.
Used in Chemical Synthesis:
In the chemical synthesis industry, (3R,4R,5S)-4-ethyl-3-fluoro-5-(hydroxymethyl)pyrrolidin-2-one serves as an intermediate or a key component in the production of various specialty chemicals, taking advantage of its reactive sites and structural features to form complex molecules with specific properties.

Upstream product

• 17342-08-4 (S)-Pyroglutaminol 
• 203871-49-2 (S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one 
• 99208-71-6 (5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane 

Downstream Products

• 1817626-54-2 PF-06650833 
• 1817626-54-2 1-(((2S,3S,4R)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl)methoxy)-7-methoxyisoquinoline-6-carboxamide 

Relevant articles and documents

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

QUINOLINE COMPOUNDS AS IRAK INHIBITORS AND USES THEREOF

The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as IRAK inhibitors.

Improvements to Enable the Large Scale Synthesis of 1-{[(2S,3S,4S)-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833)

An improved process for the large scale synthesis of 1-{[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (1), a candidate currently in clinical development, was developed. Key objectives were to eliminate chro

Discovery of Clinical Candidate 1-{[(2S,3S,4S)-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833), a Potent, Selective Inhibitor of Interleukin-1 Receptor Associated Kinase 4 (IRAK4), by Fragment-Based Drug Design

Through fragment-based drug design focused on engaging the active site of IRAK4 and leveraging three-dimensional topology in a ligand-efficient manner, a micromolar hit identified from a screen of a Pfizer fragment library was optimized to afford IRAK4 inhibitors with nanomolar potency in cellular assays. The medicinal chemistry effort featured the judicious placement of lipophilicity, informed by co-crystal structures with IRAK4 and optimization of ADME properties to deliver clinical candidate PF-06650833 (compound 40). This compound displays a 5-unit increase in lipophilic efficiency from the fragment hit, excellent kinase selectivity, and pharmacokinetic properties suitable for oral administration.

Bicyclic-Fused Heteroaryl or Aryl Compounds

Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.