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

General 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 complex chemical compound with a long name. It is a pyrrolidine derivative that contains a benzyl group, an ethyl group, and a carbamate group. The compound also includes a tosyl group, an amino group, and an acetyl group. This chemical structure suggests that it may be a potential candidate for pharmaceutical applications, such as in the development of new drugs or therapeutic agents. Further research and analysis would be needed to fully understand the potential uses and properties of this compound.

Upstream product

• 51814-19-8 1-Benzyloxycarbonyl-4-ethoxycarbonyl-3-oxopyrrolidine 
• 1201186-54-0 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine 
• 98-59-9 p-toluenesulfonyl chloride 
• 875781-41-2 5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine 
• 1145-81-9 ethyl 2-(benzyloxycarbonylamino)ethanoate 
• 1268520-70-2 C₁₂H₂₁NO₄ 
• 24410-84-2 ethyl (2E)-pentenoate 
• 875781-43-4 2-bromo-5H-pyrrolo[2,3-b]pyrazine 

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.

Synthesis method of JAK (Janus Kinase) inhibitor

The invention discloses a synthesis method of a JAK (Janus Kinase) inhibitor. The synthesis method comprises the following steps: carrying out condensation on an intermediate A-8 and an intermediate B-3 to obtain an intermediate AB-1; carrying out deprotection on the intermediate AB-1 to obtain an intermediate AB-2; carrying out cyclization on the AB-2 to obtain an intermediate AB-3; carrying outthe deprotection on the intermediate AB-3 to obtain an intermediate AB-4; carrying out the deprotection on the AB-4 again to obtain an intermediate AB-5; carrying out condensation reaction on the AB-5to obtain the JAK inhibitor 1. The synthesis method disclosed by the invention has the main advantages that the intermediate A-8 is prepared through a chiral catalysis method in a high-yield and high-chiral-purity manner, and the intermediate B-3 and the JAK inhibitor 1 are prepared in a high-yield manner. Useless enantiomers are nearly not generated so that the pressure on the environment is reduced; meanwhile, the reaction yield is high, the operation is simple and the post-treatment is simple and convenient. According to the synthesis method, reaction conditions also can be applied to large-batch preparation and are suitable for industrial production, so that the synthesis method has relatively high practical value and social and economic benefits.

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.