328955-57-3

Basic information

• Product Name: 6-Amino-4-trifluoromethylquinolin-2(1H)-one
• Synonyms: 6-Amino-4-trifluoromethylquinolin-2(1H)-one;6-Amino-4-trifluoromethyl-1H-quinolin-2-one
• CAS NO: 328955-57-3
• Molecular Formula: C₁₀H₇F₃N₂O
• Molecular Weight: 228.1705896
• Mol File: 328955-57-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-Amino-4-trifluoromethylquinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Amino-4-trifluoromethylquinolin-2(1H)-one(328955-57-3)
• EPA Substance Registry System: 6-Amino-4-trifluoromethylquinolin-2(1H)-one(328955-57-3)

Safety Data

• Hazardous Substances Data: 328955-57-3(Hazardous Substances Data)

Usage

Description

6-Amino-4-trifluoromethylquinolin-2(1H)-one is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals. It is characterized by its unique molecular structure, which includes a quinolinone core with an amino group at the 6th position and a trifluoromethyl group at the 4th position. 6-Amino-4-trifluoromethylquinolin-2(1H)-one plays a significant role in the development of therapeutic agents for various medical conditions.

Uses

Used in Pharmaceutical Industry:
6-Amino-4-trifluoromethylquinolin-2(1H)-one is used as an intermediate in the synthesis of LGD-2226 (L397615), an orally active potent and selective androgen receptor modulator. This modulator is utilized in the treatment of muscle wasting and osteoporosis, as it has been shown to have an anabolic effect on muscle and bone tissue. 6-Amino-4-trifluoromethylquinolin-2(1H)-one's unique structure allows for the development of targeted therapies that can help improve the quality of life for patients suffering from these conditions.

Synthesis

6-Amino-4-trifluoromethylquinolin-2(1H)-one is obtained by reacting Nitro-compound with hydrogen in the presence of 5% Pd/C.Experimental Procedure：A suspension of the 17.0 g 6-Nitro-4-trifluoromethylquinolin-2(1H)-one in 400 ml ethanol in a 1 L round flask was flushed with argon and 2.0 g 5% Pd/C was added. The mixture was stirred under a hydrogen atmosphere for 2 days. Then filtered through silica and washed with 1500 mL ethanol. The filtrate was evaporated under vacuum to yield 14.0 g of a bright yellow solid 6-Amino-4-trifluoromethylquinolin-2(1H)-one (92%).

Upstream product

• 328956-38-3 6-nitro-4-trifluoromethylquinolin-2(1H)-one 
• 25199-84-2 4-(trifluoromethyl)quinolin-2(1H)-one 
• 62-53-3 aniline 
• 836-31-7 4,4,4-trifluoro-3-oxo-N-phenylbutyramide 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 122-80-5 N-acetyl-p-phenylenediamine 

Downstream Products

• 328947-81-5 6-Dimethylamino-4-trifluoromethyl-2(1H)-quinolinone 

Relevant articles and documents

Novel selective androgen receptor modulators: SAR studies on 6-bisalkylamino-2-quinolinones

A series of selective androgen receptor modulators (SARMs) with a wide spectrum of receptor modulating activities was developed based on optimization of the 4-substituted 6-bisalkylamino-2-quinolinones (3). Significance of the trifluoromethyl group on the side chains and its interactions with amino acid residues within the androgen receptor (AR) ligand binding domain are discussed. A representative analog (9) was tested orally in a rodent model of hypogonadism and demonstrated desirable tissue selectivity.

Bicyclic androgen and progesterone receptor modulator compounds and methods

The present invention is directed to compounds, pharmaceutical compositions, and methods for modulating processes mediated by AR and PR. More particularly, the invention relates to nonsteroidal compounds and compositions that are high affinity, high specificity agonists, partial agonists (i.e., partial activators and/or tissue-specific activators) and antagonists for AR and PR. Also provided are methods of making such compounds and pharmaceutical compositions, as well as critical intermediates used in their synthesis.