419550-79-1

Basic information

• Product Name: 5-amino-3-methyl-4-(4-methoxyphenyl)-1Н-pyrazole
• Synonyms: 5-amino-3-methyl-4-(4-methoxyphenyl)-1Н-pyrazole
• CAS NO: 419550-79-1
• Molecular Weight: 203.244
• Mol File: 419550-79-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 5-amino-3-methyl-4-(4-methoxyphenyl)-1Н-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-3-methyl-4-(4-methoxyphenyl)-1Н-pyrazole(419550-79-1)
• EPA Substance Registry System: 5-amino-3-methyl-4-(4-methoxyphenyl)-1Н-pyrazole(419550-79-1)

Safety Data

• Hazardous Substances Data: 419550-79-1(Hazardous Substances Data)

Usage

Description

5-amino-3-methyl-4-(4-methoxyphenyl)-1Н-pyrazole is an organic compound with the molecular formula C10H12N2O. It is a derivative of pyrazole, a five-membered heterocyclic compound with two nitrogen atoms. 5-amino-3-methyl-4-(4-methoxyphenyl)-1Н-pyrazole features a methyl group at the 3rd position, an amino group at the 5th position, and a 4-methoxyphenyl group at the 4th position. Its structural characteristics make it a versatile building block in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
5-amino-3-methyl-4-(4-methoxyphenyl)-1Н-pyrazole is used as a key intermediate in the synthesis of Pyrazolopyrimidinone compounds. These compounds have been identified for their potential to inhibit the activity of PASK (P21-activated kinase), a protein kinase involved in various cellular processes, including cell growth, differentiation, and apoptosis. By inhibiting PASK, these compounds may have therapeutic applications in the treatment of various diseases, particularly those related to uncontrolled cell proliferation, such as cancer.

Upstream product

• 63895-78-3 2-(4-methoxyphenyl)-3-oxobutanenitrile 
• 1780-72-9 4-bromo-5-methyl-1H-pyrazol-3-amine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-47-2 p-methoxybenzylnitrile 

Downstream Products

• 1028361-99-0 C₁₆H₂₁N₃O₃ 
• 1363281-17-7 (S)-(1-(3-(4-methoxyphenyl)-7-phenyl-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)methanol 
• 1363293-21-3 5-chloro-3-(4-methoxyphenyl)-7-phenyl-2-methylpyrazolo[1,5-a]pyrimidine 
• 1363283-76-4 (S)-(1-(3-(4-methoxyphenyl)-7-(3-(trifluoromethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)methanol 
• 1363293-59-7 5-chloro-3-(4-methoxyphenyl)-7-(3-(trifluoromethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidine 
• 1363293-19-9 3-(4-methoxyphenyl)-7-phenyl-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one 
• 1363293-57-5 3-(4-methoxyphenyl)-7-(3-(trifluoromethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one 
• 1404447-11-5 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404446-86-1 5-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1241965-80-9 C₁₉H₂₂N₄O₃ 
• 908520-77-4 C₁₈H₁₈N₄O₂ 
• 1150233-91-2 C₁₃H₁₆N₄O 
• 1186694-58-5 C₁₆H₁₈N₄O₃ 
• 195055-88-0 [3-(4-methoxy-phenyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-dipropyl-amine 

Relevant articles and documents

The Suzuki-Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction

The efficient Suzuki-Miyaura cross-coupling reaction of halogenated aminopyrazoles and their amides or ureas with a range of aryl, heteroaryl, and styryl boronic acids or esters has been developed. The method allowed incorporation of problematic substrates: aminopyrazoles bearing protected or unprotected pyrazole NH, as well as the free amino or N-amide group. Direct comparison of the chloro, bromo, and iodopyrazoles in the Suzuki-Miyaura reaction revealed that Br and Cl derivatives were superior to iodopyrazoles, as a result of reduced propensity to dehalogenation. Moreover, the mechanism and factors affecting the undesired dehalogenation side reaction were revealed.

Study of regioselectivity of reactions between 3(5)-aminopyrazoles and 2-acetylcycloalkanones

Regioselectivity was examined of reactions between nine 3(5)-aminopyrazoles and 2-acetylcyclopentanone and 2-acetylcyclohexanone under various conditions. A series of cyclopenta[e]pyrazolo-[1,5-a]pyrimidines was obtained. The highest regioselectivity of the reaction was observed in alcohol at 20°C in the presence of a catalytic quantity of trifl uoroacetic acid. The regiostructure of compounds was established by 1H and 13C NMR spectroscopy. Pleiades Publishing, Ltd., 2012.

NOVEL COMPOUNDS FOR THE TREATMENT OF DISEASES ASSOCIATED WITH AMYLOID OR AMYLOID-LIKE PROTEINS

The present invention relates to compounds of the general formula (I) wherein (formula 2) independently represents a single bond or a double bond, represents a linking group A and A′ are each independently a 5- to 7-membered heterocyclic ring, wherein the heterocyclic rings A und A′ are optionally substituted by one or more substituents, selected from C1-6 alkyl, C3-6 cycloalkyl, optionally substituted phenyl, optionally substituted heteroaryl, C1-4 alkylene-(optionally substituted phenyl) and C1-4 alkylene-(optionally substituted heteroaryl), or two substituents may be joined to form an optionally substituted, saturated, unsaturated or aromatic 5- to 7-membered ring which is fused with the heterocyclic ring A or A′, and wherein the heterocyclic rings A und A′ may contain in addition to the units X, X′, Y and Y′ one or more heteroatoms, selected from N, NR, S and Ol wherein R is selected from H and C1-4 alkyl; the units X and X′ are each independently a H-bond acceptor; and the units Y and Y′ are each independently a H-bond donor. The compound of formula (I) can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein, such as Alzheimer's disease, and of diseases or conditions associated with amyloid-like proteins. The compounds of the present invention can also be used in the treatment of ocular diseases associated with pathological abnormalities/changes in the tissues of the visual system.