174790-35-3

Basic information

• Product Name: 3-broMo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole
• Synonyms: 3-broMo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole
• CAS NO: 174790-35-3
• Molecular Formula: C6H7BrN2
• Molecular Weight: 187.03718
• Mol File: 174790-35-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: No Data Available
• Appearance: No Data Available
• CAS DataBase Reference: 3-broMo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-broMo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole(174790-35-3)
• EPA Substance Registry System: 3-broMo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole(174790-35-3)

Safety Data

• Hazardous Substances Data: 174790-35-3(Hazardous Substances Data)

Usage

Description

3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole is a chemical compound belonging to the pyrazole family. It is characterized by its unique molecular structure, which features a bromine atom at the 3rd position and a dihydro ring system. 3-broMo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole is of interest in the field of medicinal chemistry due to its potential applications in the development of various therapeutic agents.

Uses

Used in Pharmaceutical Industry:
3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole is used as a key intermediate in the synthesis of withasomnine molecules, which are pyrazole alkaloids. These alkaloids are known for their anti-inflammatory and analgesic properties, making them valuable in the development of new drugs for the treatment of pain and inflammation.
Used in Anti-inflammatory Applications:
3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole is used as a precursor for the development of anti-inflammatory compounds. Its incorporation into withasomnine molecules enhances their ability to modulate inflammatory pathways, providing potential therapeutic benefits for conditions characterized by chronic inflammation.
Used in Analgesic Applications:
In addition to its anti-inflammatory potential, 3-Bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole is also used in the development of analgesic agents. The resulting withasomnine molecules exhibit pain-relieving properties, offering a promising avenue for the creation of new medications to alleviate acute and chronic pain.

Upstream product

• 107862-65-7 5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole 
• 174790-34-2 3-(3-chloropropyl)-1H-pyrazole 
• 76328-94-4 6-chlorohexa-1-en-3-one 
• 1429913-29-0 1,2-dibromo-6-chlorohexan-3-one 

Downstream Products

• 1314138-13-0 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole 
• 10183-74-1 withasomnine 
• 1426535-54-7 3-(4-chlorophenyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole 
• 1260667-91-1 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde 

Relevant articles and documents

Synthesis of (5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)methanamine

This short paper reports the development of a new method for the synthesis of (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine. Pyrazole was initially protected with an N-SEM protective group, followed by alkylation at C-5 position with 1-bromo-3-chloropropane. Following SEM deprotection, the intramolecular ring was closed and then a bromine atom (Br) was introduced with N-bromosuccinimide (NBS) by electrophilic aromatic substitution (SEAr), forming 3-bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole. The Br group was subsequently converted into aldehyde group, then into oxime. The final step of hydrogenation resulted in the desired product. The overall yield through the 8-step reaction process was found to be 29.4%. The intermediates and final product were identified by HPLC-MS and 1H NMR. This development provides a novel synthetic route to the formation of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole skeleton.

Dihydropyrrolo[1,2-b]pyrazoles: Withasomnine and related compounds

In the paper we indicate the increasing importance of derivatives containing a dihydropyrrolo[1,2-b]pyrazole (DPP) core. We try to show our synthetic approach based on an improved Kulinkovich method as well as our new synthetic pathway. A complex methodology involving the preparation of substituted DPPs focuses on withasomnine and the synthesis of several structurally related compounds. The developed reaction protocols enable the preparation of the mentioned bicyclic system with broadly diverse substitution. Thus, we are able to prepare systems with aliphatic, aromatic, polyaromatic, heteroaromatic, TMS, and even adamantane substitution with known biologically active properties. The reaction protocol, consisting of two multi-step synthetic pathways, includes Sonogashira and Suzuki-Miyaura cross-coupling reactions, allenyl synthon formation, Kulinkovich cyclopropanation, ring transformations, and nonsymmetrical homoallenyl azines cycloadditions. Moreover, we prepared compounds with a resemblance to other bioactive species: fadrozole, nagstatine, an antitumor agent LY2109761 and a mixed lineage kinase 7 inhibitor DHP-2.

2-PYRIDYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS

The invention provides certain 2-pyridyl carboxamide-containing compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein A and B are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.