110862-46-9

Basic information

• Product Name: N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide
• Synonyms: 5-(4-Fluorophenyl)-2-(1-Methylethyl)-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxaMide;N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide;5-(4-fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxamide
• CAS NO: 110862-46-9
• Molecular Formula: C₂₉H₂₇FN₂O₂
• Molecular Weight: 454.5352832
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 110862-46-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide(110862-46-9)
• EPA Substance Registry System: N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide(110862-46-9)

Safety Data

• Hazardous Substances Data: 110862-46-9(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxamide is used as an intermediate in the synthesis of rac-3-Oxo Atorvastatin Sodium Salt (O847150) for the development of medications to treat metabolic diseases. Its role in the synthesis process is crucial for creating effective treatments that can help manage and alleviate the symptoms of these conditions.
2. Used in Metabolic Disease Treatment:
N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxamide contributes to the creation of rac-3-Oxo Atorvastatin Sodium Salt (O847150), which is employed in the treatment of metabolic diseases. The compound plays a significant role in the development of pharmaceuticals that can improve the quality of life for patients suffering from such diseases by regulating their metabolic functions and providing relief from associated health issues.

Upstream product

• 110862-45-8 1-<2-(1,3-dioxolan-2-yl)ethyl>-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide 
• 125971-57-5 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide 
• 62-53-3 aniline 
• 42558-54-3 Methyl 4-methyl-3-oxopentanoate 
• 124401-38-3 4-methyl-3-oxo-N-phenylpentanamide 
• 125971-96-2 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide 
• 110862-43-6 α-<<2-(1,3-dioxolan-2-yl)ethyl>(2-methyl-1-oxopropyl)amino>-4-fluorobenzeneacetic acid, ethyl ester 
• 110862-44-7 α-<<2-(1,3-dioxolan-2-yl)ethyl>(2-methyl-1-oxopropyl)amino>-4-fluorobenzeneacetic acid 

Downstream Products

• 1426655-65-3 (R)-isopropyl 7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-pheny1-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxoheptanoate 
• 134523-03-8 lipitor 
• 1112262-71-1 2-((4R,6R)-6-(2-(3-(phenylcarbamoyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid isopropyl ester 
• 1035205-25-4 (3R,5R)-isopropyl 7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate 
• 110862-47-0 methyl 7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate 
• 134394-96-0 *,S^*)>-5-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-3-hydroxy-1-pentanoic acid, 2-hydroxy-1,2,2-triphenylethyl ester 
• 95061-46-4 (R)-1,1,2-triphenylethane-1,2-diol 
• 134394-96-0 (S)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid (S)-2-hydroxy-1,2,2-triphenylethyl ester 
• 777093-53-5 C₃₂H₃₁FN₂O₂ 
• 777093-50-2 C₃₂H₃₁FN₂O₂ 
• 777093-44-4 C₃₂H₃₁FN₂O₂ 
• 134523-07-2 (-)-(4S)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1-<(tetrahydro-4-hydroxy-2-oxo-2H-pyran-6-yl)ethyl>-1H-pyrrole-4-carboxamide 
• 125995-03-1 atorvastatin lactone 
• 110862-39-0 (+/-)-trans-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-<2-tetrahydro-4-hydroxy-6-oxo-2H-pyran-6-yl)ethyl>-1H-pyrrole-3-carboxamide 

Relevant articles and documents

The total synthesis of calcium atorvastatin

A practical and convergent asymmetric route to calcium atorvastatin (1) is reported. The synthesis of calcium atorvastatin (1) was performed using the remote 1,5-anti asymmetric induction in the boron-mediated aldol reaction of β-alkoxy methylketone (4) with pyrrolic aldehyde (3) as a key step. Calcium atorvastatin was obtained from aldehyde (3) after 6 steps, with a 41% overall yield.

Synthetic studies on statins. Part 1: A short and cyanide-free synthesis of atorvastatin calcium via an enantioselective aldol strategy

A short and cyanide-free enantioselective synthesis of atorvastatin calcium has been achieved starting from a commercially available highly substituted 1,4-diketone in an overall yield of 40%. The key step in this approach is the asymmetric aldol reaction of an aldehyde with diketene in the presence of Ti(O-i-Pr)4-Schiff base complex to create the (5R)-stereochemistry of atorvastatin calcium.

PROCESS FOR THE PREPARATION OF ATORVASTATIN AND INTERMEDIATES

A process is provided for preparing (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, R-substituted ester 9 comprising: (a) reacting the aldehyde 1 with the enolate form of (S)-2-hydroxy-1,2,2-triphenylethyl acetate substituent in a chelating co-solvent; (b) hydrolysis of (R,S)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (S)-2-hydroxy-1,2,2-triphenylethyl ester (2a and 2b) using a base, preferably an alkali metal base, preferably in a solvent to form the carboxylic acid 7; (c) treating the acid 7 with a chiral base to form a salt and purifying the salt to obtain enantiomerically enriched (R)-7 chiral base salt; (d) alkylation of the (R)-7 chiral base salt or the free base derived from (R)-7, forming (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, R-substituted ester 9 and atorvastatin calcium 6, wherein R is a C1 to C6 alkyl, C6 to C9 aryl or C7 to C10 aralkyl.

Process for trans-6-(2-(substituted-pyrrol-1-yl)alkyl)pryan-2-one inhibitors of cholesterol synthesis

An improved process for the preparation of trans-6-[2-(substituted-pyrrol-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where 1,6-heptadien-4-ol is converted in eight operations to the desired products, as well as an improved process for the preparation of (2R-trans) and trans-(±)-5-(4-fluorophenyl)-2-(1-methylethyl)-N-4-diphenyl-1-[2-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide by a novel synthesis where 4-methyl-3-oxo-N-phenylpentanamide is converted in eight operations to the desired product or alternatively 4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide is converted in one step to the desired product, and additionally, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide from (R)-4-cyano-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]butanoic acid, as well as other valuable intermediates used in the processes.

Inhibitors of Cholesterol Biosynthesis. 3. Tetrahydro-4-hydroxy-6--2H-pyran-2-one Inhibitors of HMG-CoA Reductase. 2. Effects of Introducing Substituents at Positions Three and Four of the Pyrrole Nucleus

A series of trans-tetrahydro-4-hydroxy-6--2H-pyran-2 ones and their dihydroxy acids were prepared and tested for their ability to inhibit the enzyme HMG-CoA reductase in vitro.Inhibitory potency was found to increase subtantially when substituents were introduced into positions three and four of the pyrrole ring.A systematic exploration of structure-activity relationships at these two positions led to the identification of a compound ((+)-33, (+)-(4R)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1- -1H-pyrrole-4-carboxamide) with five times the inhibitory potency of the fungal metabolite compactin.