59942-84-6

Basic information

• Product Name: Pyrazolo[1,5-a]pyridine, 2-(1-methylethyl)- (9CI)
• Synonyms: Pyrazolo[1,5-a]pyridine, 2-(1-methylethyl)- (9CI);2-Isopropyl-pyrazolo[1,5-a]pyridine;Pyrazolo[1,5-a]pyridine,2-(1-methylethyl)-
• CAS NO: 59942-84-6
• Molecular Formula: C₁₀H₁₂N₂
• Molecular Weight: 160.21568
• Product Categories: ISOPROPYL
• Mol File: 59942-84-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• CAS DataBase Reference: Pyrazolo[1,5-a]pyridine, 2-(1-methylethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazolo[1,5-a]pyridine, 2-(1-methylethyl)- (9CI)(59942-84-6)
• EPA Substance Registry System: Pyrazolo[1,5-a]pyridine, 2-(1-methylethyl)- (9CI)(59942-84-6)

Safety Data

• Hazardous Substances Data: 59942-84-6(Hazardous Substances Data)

Usage

Uses

2-Isopropylpyrazolo[1,5-a]pyridine is an intermediate in the synthesis of AV1013 (2-Amino-1-[2-(1-methylethyl) pyrazolo[1,5-a] pyridin-3-yl]-1-propanone hydrochloride) (A618170), which is a drug candidate for the treatment of neuropathic pain, addiction behavior and drug withdrwal symptoms.

Upstream product

• 50847-11-5 ibudilast 
• 7583-90-6 1-amino-2-methylpyridinium iodide 
• 97-72-3 2-Methylpropionic anhydride 
• 141418-09-9 2-(prop-1-en-2-yl)pyrazolo[1,5-a]pyridine 
• 126959-38-4 (2-isopropyl-pyrazolo[1,5-a]pyridin-3-carboxylic acid) 
• 109-06-8 α-picoline 
• 10330-59-3 3-methyl-1-(pyridin-2-yl)butan-2-one 

Downstream Products

• 95569-25-8 (4-Fluoro-phenyl)-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-methanone 
• 95542-59-9 (2-isopropylpyrazolo[1,5-a]pyridin-3-yl)(4-methoxyphenyl)methanone 
• 95542-51-1 2-isopropyl-3-(p-nitrobenzoyl)pyrazolo<1,5-α>pyridine 
• 121346-56-3 2-isopropyl-3-(4-methoxybenzenesulphonyl)-pyrazolo[1,5-a]pyridine 
• 95542-55-5 2-isopropyl-4,5,6,7-tetrahydropyrazolo<1,5-α>pyridine 
• 95542-53-3 3-(p-benzoylaminobenzoyl)-2-isopropylpyrazolo<1,5-α>pyridine 
• 95542-69-1 N-[4-(2-Isopropyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridine-3-carbonyl)-phenyl]-benzamide 
• 95542-70-4 N-[4-(2-Isopropyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridine-3-carbonyl)-phenyl]-acetamide 
• 95542-61-3 N-[4-(2-Isopropyl-pyrazolo[1,5-a]pyridine-3-carbonyl)-phenyl]-acetamide 
• 95542-66-8 (2-Isopropyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridin-3-yl)-(4-nitro-phenyl)-methanone 
• 95542-63-5 (4-Butylamino-phenyl)-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-methanone 
• 95542-71-5 (4-Butylamino-phenyl)-(2-isopropyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridin-3-yl)-methanone 
• 95569-24-7 (4-Ethylamino-phenyl)-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-methanone 
• 95569-30-5 (4-Amino-3-methyl-phenyl)-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-methanone 

Relevant articles and documents

Synthesis of metabolites and related compounds of 3-isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine (ibudilast). I. Metabolites of alkyl side chains

3-Isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine (ibudilast) has a large number of metabolites. In order to unequivocally establish the true identity of these metabolites, we prepared a series of authentic reference compounds, namely novel pyrazolo[1,5-a]pyridine derivatives with mono- and dihydroxylated alkyl side chains and carboxylated alkyl side chains. These results lead to the conclusion that reactions at the 3-position of pyrazolo[1,5-a]pyridine are governed by the electron-donating effect and the weak basicity of bridge-head nitrogen. On the basis of these results we were able to establish a method of functional group introduction to the alkyl side chains of pyrazolo[1,5-a]pyridine.

ENANTIOMERIC COMPOSITIONS OF 2-AMINO-1-(2-ISOPROPYLPYRAZOLO[1,5-a]PYRIDIN-3-YL)PROPAN-1-ONE AND RELATED METHODS

Enantiomerically pure (S)-2-amino-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one, (S)-AV1013, is a candidate therapeutic for treating neuroathic pain, addiction behavior and drug withdrawal symptoms. Also described are methods for preparing and using (S)-AV1013, its pharmaceutically acceptable salts as well as pharmaceutically acceptable formulations of the same.

SUBSTITUTED PYRAZOLO [1,5-α] PYRIDINE COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to substituted pyrazolo[l,5-α]pyridines and related methods for their synthesis and use.