1428243-27-9

Basic information

• Product Name: (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate
• Synonyms: (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate
• CAS NO: 1428243-27-9
• Molecular Weight: 661.779
• Mol File: 1428243-27-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate(1428243-27-9)
• EPA Substance Registry System: (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate(1428243-27-9)

Safety Data

• Hazardous Substances Data: 1428243-27-9(Hazardous Substances Data)

Usage

Description

(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate is a pyrrolidine derivative featuring a benzyl group, an ethyl group, and a carbamate group. It also incorporates a tosyl group, an amino group, and an acetyl group, indicating its potential as a pharmaceutical candidate for the development of new drugs or therapeutic agents.

Uses

Used in Pharmaceutical Industry:
(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate is used as a potential drug candidate for the development of new therapeutic agents, given its complex chemical structure and the presence of various functional groups that may contribute to its pharmacological properties. Further research and analysis are required to explore its full potential and applications in medicine.

Upstream product

• 55314-57-3 ethyl pent-2-ynoate 
• 27805-84-1 (cis)-2-pentenoic acid ethyl ester 
• 1428243-25-7 (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid (R)-1-(naphthalen-1-yl)ethan-1-amine salt 
• 1201187-44-1 N-(5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazin-2-yl)carbamic acid tert-butyl ester 
• 1428243-26-8 (3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate 
• 875781-43-4 2-bromo-5H-pyrrolo[2,3-b]pyrazine 
• 1268520-70-2 C₁₂H₂₁NO₄ 
• 1145-81-9 ethyl 2-(benzyloxycarbonylamino)ethanoate 
• 875781-41-2 5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1201186-54-0 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine 
• 51814-19-8 1-Benzyloxycarbonyl-4-ethoxycarbonyl-3-oxopyrrolidine 

Downstream Products

• 1310726-60-3 (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide 
• 1428243-28-0 8-((3R,4S)-4-ethylpyrrolidin-3-yl)-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine 

Relevant articles and documents

Development of a Scalable Enantioselective Synthesis of JAK Inhibitor Upadacitinib

Process development of a six-stage synthesis of upadacitinib, a JAK1 inhibitor, is described. It is highlighted by an enantioselective and diastereoselective hydrogenation of a tetrasubstituted olefin to set the two pyrrolidine stereocenters. Preparation of the main fragments and strategies to link them together, optimization of the imidazole cyclization, and in-depth understanding of the formation of the urea moiety at the final stage are discussed.

ALTERNATE PROCESSES FOR THE PREPARATION OF PYRROLIDINE DERIVATIVES

Aspects of the present application relate to process for the preparation of Pyrrolidine derivatives useful as key intermediates for active ingredients. Specific aspects relate to alternate process for the preparation of Upadacitinib intermediate, 4-ethylpyrrolidine-3-carboxylic acid, its ester or a salt thereof. Processes disclosed here in are cost effective and industrially viable as compared to known processes.

Upadacitinib tartrate: Tyrosine-protein kinase JAK1 inhibitor Treatment of autoimmune inflammatory diseases Treatment of rheumatoid arthritis

Upadacitinib tartrate (ABT-494) is a potent and selective tyrosine-protein kinase JAK1 inhibitor being developed for the treatment of systemic autoimmune inflammatory diseases, including rheumatoid arthritis (RA), Crohn's disease, ulcerative colitis and psoriatic arthritis. In vitro, upadacitinib demonstrated higher selectivity for inhibiting JAK1 over JAK2 and JAK3, suggesting a potentially improved therapeutic profile in treating patients with inflammatory diseases compared to nonselective JAK inhibitors. Upadacitinib has demonstrated safety and efficacy in phase II trials in patients with RA and inflammatory bowel disease, and is currently in phase III development for these indications.