376348-77-5

Basic information

• Product Name: 4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE
• Synonyms: 4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE;(S)-4,4-difluoro-N-(3-hydroxy-1-phenylpropyl)cyclohexanecarboxaMide;Cyclohexanecarboxamide, 4,4-difluoro- N-[(1S)-3-hydroxy-1-phenylpropyl]-;UK 453465;4,4-Difluoro-N-((1S)-3-hydroxy-1-phenylpropyl)cyclohexanecarboxamide;(S)-4,4-difluoro-N-(3-hydroxy-1-phenylpropyl)cyclohexanecarboxamide(WXG02011)
• CAS NO: 376348-77-5
• Molecular Formula: C₁₆H₂₁F₂NO₂
• Molecular Weight: 297.34
• EINECS: 638-778-4
• Mol File: 376348-77-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 119.2 °C
• Boiling Point: 502.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• PKA: 14.65±0.40(Predicted)
• CAS DataBase Reference: 4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE(376348-77-5)
• EPA Substance Registry System: 4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE(376348-77-5)

Safety Data

• Hazardous Substances Data: 376348-77-5(Hazardous Substances Data)

Usage

General Description

4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE, also known as Lorcaserin, is a chemical compound that acts as a selective serotonin 2C receptor agonist and has been used as a weight-loss drug. It works by affecting the brain's appetite control center to reduce food intake and promote weight loss in obese individuals. Lorcaserin was approved by the Food and Drug Administration (FDA) in 2012 but was subsequently withdrawn from the market in 2020 due to safety concerns regarding an increased risk of cancer. Despite its withdrawal, it continues to be of interest in research due to its potential therapeutic effects on other conditions, such as type 2 diabetes and cardiovascular diseases.

Upstream product

• 340188-50-3 ethyl (S)-3-amino-3-phenyl-propionate hydrochloride 
• 376348-75-3 4,4-difluorocyclohexane-1-carbonyl chloride 
• 376348-76-4 ethyl (S)-3-[(4,4-difluorocyclohexyl)carboxamido]-3-phenylpropanoate 
• 122665-97-8 4,4-difluorocyclohexanecarboxylic acid 
• 376348-78-6 4,4-difluorocyclohexanecarboxylic acid (3-oxo-1-phenyl-propyl)-amide 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 

Downstream Products

• 376348-78-6 4,4-difluorocyclohexanecarboxylic acid (3-oxo-1-phenyl-propyl)-amide 
• 674782-29-7 maraviroc 

Relevant articles and documents

METHOD FOR PREPARING MARAVIROC

Provided is a method for preparing a tropane derivative, maraviroc, including reacting a compound of formula (II) with a compound of formula (I), wherein the compound of formula (II) is prepared by the steps of acetylation of a compound of formula (III), activation and substitution of a compound of formula (IV) by a chlorination agent, cyclization of a compound of formula (V), and debenzylation of a compound of formula (VI) by hydrogenation. Hence, the present disclosure provides a method for preparing maraviroc with good yield and simple operation.

Process research and scale-up of a commercialisable route to maraviroc (UK-427,857), a CCR-5 receptor antagonist

A six-step synthetic route to the CCR-5 receptor antagonist, Maraviroc (UK-427,857) (1) has been developed and demonstrated at scale in a pilot plant. The route has supported four Pilot-Plant campaigns and has produced multikilogram quantities of 1. Continued development of the synthetic route has resulted in a robust process with improved throughput compared to that of the original synthesis (Haycock-Lewandowski, S. J.; Mawby, N. J.; Wilder, A.; Ahman, J. Org. Process Res. Dev. 2008, 12, 1094-1103).