Laropiprant

Base Information

• Chemical Name: Laropiprant
• CAS No.: 571170-77-9
• Deprecated CAS: 895565-43-2
• Molecular Formula: C21H19ClFNO4S
• Molecular Weight: 435.904
• European Community (EC) Number: 682-424-1
• UNII: G7N11T8O78
• DSSTox Substance ID: DTXSID60205756
• Nikkaji Number: J2.140.283D
• Wikipedia: Laropiprant
• Wikidata: Q412291
• NCI Thesaurus Code: C87372
• Pharos Ligand ID: CWKU69N7GNF7
• Metabolomics Workbench ID: 152755
• ChEMBL ID: CHEMBL426559
• Mol file: 571170-77-9.mol

Synonyms:(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl acetic acid;laropiprant;MK-0524

Chemical Property of Laropiprant

Chemical Property:

• Appearance/Colour: White to off-white solid
• Melting Point: 175∶C
• Boiling Point: 710.014 °C at 760 mmHg
• PKA: 4.54±0.10(Predicted)
• Flash Point: 383.203 °C
• PSA: 84.75000
• Density: 1.486 g/cm³
• LogP: 5.47090
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 435.0707351
• Heavy Atom Count: 29
• Complexity: 721

Purity/Quality:

98%,99%, ^*data from raw suppliers

Laropiprant(MK-0524) 99.85% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)C1=CC(=CC2=C1N(C3=C2CCC3CC(=O)O)CC4=CC=C(C=C4)Cl)F
• Isomeric SMILES: CS(=O)(=O)C1=CC(=CC2=C1N(C3=C2CC[C@@H]3CC(=O)O)CC4=CC=C(C=C4)Cl)F
• Recent ClinicalTrials: A Study to Evaluate the Effects of Extended Release (ER) Niacin/Laropiprant, Laropiprant, ER Niacin, and Placebo on Urinary Prostanoid Metabolites in Subjects With High Cholesterol (0524A-075)(COMPLETED)
• Recent EU Clinical Trials: Efecto de niacina/laropiprant en la concentración de lipoproteína (A) en relación a las concentraciones basales y al tama?o de lipoproteína (A).

Technology Process of Laropiprant

There total 37 articles about Laropiprant which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

[4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,4-dihydro-2H-cyclopenta[b]indol-3-ylidene]-acetic acid (866215-99-8) → [4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid + laropiprant (571170-77-9)

Guidance literature:

With hydrogen; triethylamine; [(S-BINAP)Ru(p-cymene)Cl₂]2; In methanol; at 50 ℃; for 20h; under 5430.05 Torr; Title compound not separated from byproducts;

DOI:10.1021/ja0623358

Reference yield:

[(3R)-4-(4-chlorophenyl)methyl-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b] indol-3-yl]acetic acid, TMG salt → laropiprant (571170-77-9)

Guidance literature:

[(3R)-4-(4-chlorophenyl)methyl-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b] indol-3-yl]acetic acid, TMG salt; With hydrogenchloride; In water; ethyl acetate;

In water; ethyl acetate; at 20 ℃; for 1h;

Reference yield:

[(3R)-4-(4-chlorophenyl)methyl-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b] indol-3-yl]acetic acid, DIPA salt → laropiprant (571170-77-9)

Guidance literature:

[(3R)-4-(4-chlorophenyl)methyl-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b] indol-3-yl]acetic acid, DIPA salt; With hydrogenchloride; In water; ethyl acetate;

In water; ethyl acetate; at 20 ℃; for 1h;

upstream raw materials:

[4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester

[(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid

sodium methansulfinate

(7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl)-acetic acid

Refernces

• 1、 -. "Method of Treating Pathological Blushing". Page/Page column 13-14. . Retrieved 2010/11/29.
• 2、 Tellers, David M.,McWilliams, J. Christopher,Humphrey, Guy,Journet, Michel,DiMichele, Lisa,Hinksmon, Joseph,McKeown, Arlene E.,Rosner, Thorsten,Sun, Yongkui,Tillyer, Richard D.. "On the mechanism of an asymmetric α,β-unsaturated carboxylic acid hydrogenation: Application to the synthesis of a PGD2 receptor antagonist". . p. 17063 - 17073. Retrieved 2007/10/03.