10199-50-5

Basic information

• Product Name: 5-AMINO-1-METHYL-3-PHENYLPYRAZOLE
• Synonyms: VITAS-BB TBB000664;TIMTEC-BB SBB005507;1-METHYL-3-PHENYL-1H-PYRAZOL-5-AMINE;5-AMINO-1-METHYL-3-PHENYLPYRAZOLE;BUTTPARK 30\09-85;1-methyl-3-phenyl-5-pyrazolamine;5-Amino-1-methyl-3-phenyl-1H-pyrazole;5-Amino-1-menthyl-3-phenylpyrazole
• CAS NO: 10199-50-5
• Molecular Formula: C₁₀H₁₁N₃
• Molecular Weight: 173.21
• EINECS: -0
• Mol File: 10199-50-5.mol

Chemical Properties

• Melting Point: 125-128°C
• Boiling Point: 368.1 °C at 760 mmHg
• Flash Point: 176.4 °C
• Appearance: cream crystals
• Density: 1.17 g/cm³
• Vapor Pressure: 1.3E-05mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3?+-.0.10(Predicted)
• BRN: 743807
• CAS DataBase Reference: 5-AMINO-1-METHYL-3-PHENYLPYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-METHYL-3-PHENYLPYRAZOLE(10199-50-5)
• EPA Substance Registry System: 5-AMINO-1-METHYL-3-PHENYLPYRAZOLE(10199-50-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 10199-50-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-1-METHYL-3-PHENYLPYRAZOLE is used as a selective targeting agent for the TPX2 Site of Importin-α. This application is significant because it utilizes Fragment-Based Ligand Design, a technique that allows for the development of more effective and targeted drugs. By selectively targeting the TPX2 Site of Importin-α, this compound can potentially be used in the development of therapies for various diseases, including cancer.

InChI:InChI=1/C10H11N3/c1-13-10(11)7-9(12-13)8-5-3-2-4-6-8/h2-7H,11H2,1H3

Upstream product

• 22038-72-8 methyldiazene 
• 614-16-4 Benzoylacetonitrile 
• 624-80-6 ethylhydrazine 
• 7339-53-9 methyl hydrazine hydrochloride 
• 93-89-0 benzoic acid ethyl ester 
• 1537216-91-3 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-3-phenyl-1H-pyrazole 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 54962-76-4 5-azido-1-methyl-3-phenyl-1H-pyrazole 
• 1402242-56-1 potassium trifluoro(3-hydroxy-3-phenylprop-1-yn-1-yl)borate 
• 1402242-69-6 potassium trifluoro(1-methyl-3-phenyl-1H-pyrazol-5-yl)borate 
• 1402242-62-9 potassium trifluoro(3-oxo-3-phenylprop-1-yn-1-yl)borate 
• 93-58-3 benzoic acid methyl ester 
• 60-34-4 methylhydrazine 
• 98-86-2 acetophenone 

Downstream Products

• 91623-40-4 4-cyclohex-1-enyl-2-methyl-5-phenyl-2H-pyrazol-3-ylamine 
• 81198-00-7 N-(1-methyl-3-phenyl-1H-pyrazol-5-yl)benzamide 
• 102999-05-3 1-methyl-3-phenyl-5-(4-methylbenzoyl)amidopyrazole 
• 92133-90-9 4-Methyl-N-(2-methyl-5-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide 
• 116834-98-1 1,4,6-Trimethyl-3-phenyl-1H-pyrazolo[3,4-b]pyridine 
• 116835-07-5 1,6-Dimethyl-3-phenyl-1H-pyrazolo[3,4-b]pyridine 
• 92406-23-0 ethyl 3-phenyl-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate 
• 116855-24-4 2-[1-(2-Methyl-5-phenyl-2H-pyrazol-3-ylamino)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester 
• 116855-21-1 (Z)-2-Cyano-3-(2-methyl-5-phenyl-2H-pyrazol-3-ylamino)-acrylic acid ethyl ester 
• 20481-34-9 diethyl 2-[(3-phenyl-1-methyl-1H-pyrazol-5-ylamino)methylene]malonate 
• 19848-97-6 5-Amino-1-methyl-4-nitroso-3-phenylpyrazole 

Relevant articles and documents

Design and Synthesis of Fungal-Selective Resorcylate Aminopyrazole Hsp90 Inhibitors

The molecular chaperone Hsp90, essential in all eukaryotes, plays a multifaceted role in promoting survival, virulence, and drug resistance across diverse pathogenic fungal species. The chaperone is also critically important, however, to the pathogen's hu

HSP90 INHIBITORS AND USES THEREOF

Herein is described the design and synthesis of resorcylate aminopyrazole compounds. These compounds show broad, potent and fungal-selective Hsp90 inhibitory activity. These compounds also find use in treating Hsp90 related deseases.

Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System

A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of Csp2 and Csp3 nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.

Discovery of 1H-pyrazolo[3,4-b]pyridines as potent dual orexin receptor antagonists (DORAs)

Compound rac-1 was identified by high throughput screening. Here we report SAR studies and MedChem optimization towards the highly potent dual orexin receptor antagonists (S)-2 and (S)-3. Furthermore, strategies to overcome the suboptimal physicochemical properties are highlighted and the pharmacokinetic profiles of representative compounds is presented.

Direct synthesis of pyrazoles from esters using tert-butoxide-assisted C-(C=O) coupling

This paper describes the direct synthesis of pyrazoles from esters that comprises two sequential reactions: tert-butoxide-assisted C-C(=O) coupling reaction to yield β-ketonitrile or α,β-alkynone intermediates, and condensation by hydrazine addition. The method reported allows for easy control of the regioselectivity and structure of substituents at N-1, C-3, C-4 and/or C-5 positions.

Trifluoroacetic acid: An efficient catalyst for paal-knorr pyrrole synthesis and its deprotection

In the present work, we demonstrated a simple and an efficient method for the condensation of substituted aryl/heteroaryl amines with acetonylacetone in the presence of trifluoro acetic acid to afford the corresponding 2,5-dimethyl-1-substitued pyrroles using Paal-Knorr synthesis in excellent yields. Trifluoroacetic acid was used under reflux condition for the deprotection of 2,5-dimethyl-1-substitued pyrroles to their corresponding substituted aryl/heteroaryl amines in moderate yields. 2,5-Dimethyl-1-substitued pyrrole were characterized by NMR and LC-MS. The yield of the compounds was found to be excellent.

DISUBSTITUTED HETEROARYL-FUSED PYRIDINES

The invention relates to compound of the formula (I′) in which the substituents are as defined in the specification; in free form or in salt form; to its preparation, to its use as medicament and to medicaments comprising it.

Synthesis of ynone trifluoroborates toward functionalized pyrazoles

The synthesis of a range of novel ynone trifluoroborates has been achieved, in a two-pot process from propargylic alcohols. These alkynes have been subsequently used in the formation of a range of pyrazole trifluoroborate salts via cyclization with hydrazines. The products are generated with high levels of regiocontrol and in excellent yields and represent versatile synthetic intermediates.

DISUBSTITUTED HETEROARYL-FUSED PYRIDINES

The invention relates to compound of the formula (I') in which the substituents are as defined in the specification; in free form or in salt form; to its preparation, to its use as medicament and to medicaments comprising it.

Microwave-assisted synthesis of N-pyrazole ureas and the p38α inhibitor BIRB 796 for study into accelerated cell ageing

Microwave irradiation of substituted hydrazines and β-ketoesters gives 5-aminopyrazoles in excellent yield, which can be transformed to the corresponding N-carbonyl derivatives by treatment with an isocyanate or chloroformate. Derivatization of 4-nitronaphth-1-ol using predominantly microwave heating methods and reaction with an N-pyrazole carbamate provides a rapid route to the N-pyrazole urea BIRB 796 in high purity, as a potent and selective inhibitor of p38α mitogen-activated protein kinase for the study of accelerated ageing in Werner syndrome cells. The Royal Society of Chemistry 2006.