60419-81-0

Basic information

• Product Name: 3-Amino-5-Methyl-4-Phenylpyrazole
• Synonyms: ASINEX-REAG BAS 16576928;ASISCHEM C58483;IFLAB-BB F0912-0735;CHEMBRDG-BB 4004588;5-AMINO-3-METHYL-4-PHENYLPYRAZOLE;5-METHYL-4-PHENYL-2H-PYRAZOL-3-YLAMINE;AKOS 231-04;AKOS B035598
• CAS NO: 60419-81-0
• Molecular Formula: C₁₀H₁₁N₃
• Molecular Weight: 173.21
• Mol File: 60419-81-0.mol

Chemical Properties

• Melting Point: 140-141°C
• Boiling Point: 368.5 °C at 760 mmHg
• Flash Point: 204.3 °C
• Appearance: /
• Density: 1.196g/cm³
• Vapor Pressure: 1.27E-05mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 3-Amino-5-Methyl-4-Phenylpyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-5-Methyl-4-Phenylpyrazole(60419-81-0)
• EPA Substance Registry System: 3-Amino-5-Methyl-4-Phenylpyrazole(60419-81-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 60419-81-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H11N3/c1-7-9(10(11)13-12-7)8-5-3-2-4-6-8/h2-6H,1H3,(H3,11,12,13)

Upstream product

• 140-29-4 phenylacetonitrile 
• 4468-48-8 1-phenyl-1-cyanopropan-2-one 

Downstream Products

• 690275-78-6 7-methyl-4-methylsulfanyl-8-phenyl-pyrazolo[1,5-a][1,3,5]triazin-2-ylamine 
• 331739-47-0 2,5-dimethyl-3-phenyl-pyrazolo[1,5-a]pyrimidin-7-ol 
• 712274-42-5 2-methyl-3-phenyl-7-p-tolyl-pyrazolo[1,5-a]pyrimidine 
• 838855-51-9 4-(1-methyl-3H-pyrazolo[3,4-c]isoquinolin-5-yl)phenol 
• 1161949-71-8 C₁₉H₁₂F₃N₃OS 
• 510716-34-4 5-ethoxy-2-methyl-3-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 
• 428834-91-7 2-methyl-3-phenyl-9-(trifluoromethyl)-5,6,7,8-tetrahydropyrazolo[5,1-b]quinazoline 
• 428834-02-0 2-methyl-3-phenyl-8-(trifluoromethyl)-6,7-dihydro-5H-1,4,8a-triaza-s-indacene 
• 486993-32-2 5,5-dimethyl-2-[(3-methyl-4-phenyl-1H-pyrazol-5-ylamino)methylidene]cyclohexane-1,3-dione 
• 447410-29-9 2,8,8-trimethyl-3-phenyl-8,9-dihydropyrazolo[5,1-b]quinaquinazolin-6(7H)-one 

Relevant articles and documents

Synthesis and biological evaluation of 7-(aminoalkyl)pyrazolo[1,5-a]pyrimidine derivatives as cathepsin K inhibitors

A series of novel 7-aminoalkyl substituted pyrazolo[1,5-a]pyrimidine derivatives were synthesized and tested for inhibition of cathepsin K. The synthetic methodology comprises cyclization of 5-aminopyrazoles with N-Boc-α-amino acid-derived ynones followed by transformation of the ester and the Boc-amino functions. It allows for easy diversification of the pyrazolo[1,5-a]pyrimidine scaffold at various positions. Molecular docking studies with pyrazolo[1,5-a]pyrimidine derivatives were also performed to elucidate the binding mode in the active site of cathepsin K. The synthesized compounds exhibited moderate inhibition activity (Ki ≥ 77 μM).

PYRAZOLOPYRIMIDINE DERIVATIVES AND THE COMPOSITIONS AND METHODS OF TREATMENT REGARDING THE SAME

The present disclosure is directed to pyrazolo[1,5-a]pyrimidine compounds of formula (I), pharmaceutical compositions thereof and methods for modulating or activating a Parkin ligase The present disclosure is also directed to methods of treating and/or reducing the incidence of diseases or conditions related to the activation of Parkin ligase. R21, R22, R23, R24 and R25 are as defined herein.

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.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Design, synthesis and biological activity of pyrazolo[1,5-a]pyrimidin-7(4H) -ones as novel Kv7/KCNQ potassium channel activators

Voltage-gated Kv7/KCNQ/M-potassium channels play a pivotal role in controlling neuronal excitability. Genetic reduction of KCNQ channel activity as a result of mutations causes various human diseases such as epilepsy and arrhythmia. Therefore, discovery of small molecules that activate KCNQ channels is an important strategy for clinical intervention of membrane excitability related disorders. In this study, a series of pyrazolo[1,5-a]pyrimidin-7(4H)- ones (PPOs) have been found to be novel activators (openers) of KCNQ2/3 potassium channels through high-throughput screening by using atomic absorption rubidium efflux assay. Based on structure-activity relationship (SAR), the substituted PPOs have been optimized. The 5-(2,6-dichloro-5-fluoropyridin-3-yl)- 3-phenyl-2-(trifluoromethyl) pyrazolo[1,5-a]pyrimidin-7(4H)-one (17) was identified as a novel, potent, and selective KCNQ2/3 potassium channel opener by patch-clamp recording assay.

Synthesis of pyrazolo[5,1-d][1,2,3,5]tetrazine-4(3H)-ones

A solid-phase synthesis of 5-aminopyrazole has been developed and applied to the preparation of pyrazolo[5,1-d]-[1,2,3,5]tetrazine-4(3H)-ones. In this strategy, a one-pot reaction from 5-aminopyrazoles to the pyrazolo[5,1-d]-[1,2, 3,5]tetrazine-4(3H)-ones which provided the compounds in good yields was demonstrated. Using this synthetic strategy, we prepared a representative set of 16 pyrazolo[5,1-d][l,2,3,5]tetrazine-4(3H)-ones.

ANAPLASTIC LYMPHOMA KINASE MODULATORS AND METHODS OF USE

The present invention comprises compounds and pharmaceutical compositions comprising the compounds that are inhibitors of ALK. The invention also comprises methods of using the compounds and compositions to treat diseases mediated by ALK, including diseases such as cancer, immunological disorders, cardiovascular diseases, and other degenerative disorders.

Optimization of 3-phenylpyrazolo[1,5-a]pyrimidines as potent corticotropin-releasing factor-1 antagonists with adequate lipophilicity and water solubility

In our efforts to identify potent CRF1 antagonists with proper physicochemical properties, a series of 3-phenylpyrazolo[1,5-a]pyrimidines bearing polar groups, such as amino, hydroxyl, methoxy, sulfoxide, were designed and synthesized. Several positions of the core structure were identified, where a polar group was tolerated with slight reduction in receptor binding. NBI 30545 (18n) was found to have good binding affinity and potent antagonistic activity at the human CRF1 receptor. Moreover, this compound had proper lipophilicity (logD=2.78) and good solubility in water (>10mg/mL), and exhibited good plasma and brain exposure when given orally.