(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid

Base Information

• Chemical Name: (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid
• CAS No.: 147511-69-1
• Molecular Formula: C₂₅H₂₄FNO₄
• Molecular Weight: 421.468
• Hs Code.: 3004909090
• European Community (EC) Number: 643-092-3
• NSC Number: 760423
• Wikipedia: Pitavastatin
• NCI Thesaurus Code: C87752
• RXCUI: 861640
• Mol file: 147511-69-1.mol

Synonyms:(E,3R,5S)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid;itavastatin;itavastatin calcium;nisvastatin;NK 104;NK-104;P 872441;P-872441;pitavastatin;pitavastatin calcium;pitavastatin lactone

Chemical Property of (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid

Chemical Property:

• Vapor Pressure: 4.21E-20mmHg at 25°C
• Refractive Index: 1.679
• Boiling Point: 691.961 °C at 760 mmHg
• PKA: 4.24±0.10(Predicted)
• Flash Point: 372.285 °C
• PSA: 90.65000
• Density: 1.352 g/cm³
• LogP: 4.51810
• Storage Temp.: -20°C, Hygroscopic
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 461.1315273
• Heavy Atom Count: 32
• Complexity: 631

Purity/Quality:

Capsaicin 99%, ^*data from raw suppliers

Pitavastatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C2=NC3=CC=CC=C3C(=C2C=CC(CC(CC(=O)O)O)O)C4=CC=C(C=C4)F.[Ca+2]
• Isomeric SMILES: C1CC1C2=NC3=CC=CC=C3C(=C2/C=C/[C@H](C[C@H](CC(=O)O)O)O)C4=CC=C(C=C4)F.[Ca+2]
• Recent ClinicalTrials: Repurposed Drugs in Research for Cancer Clinical Trials- Pitavastatin
• Recent EU Clinical Trials: A PHASE 3 STUDY EVALUATING THE EFFECT OF PITAVASTATIN TO PREVENT CARDIOVASCULAR EVENTS IN HIV-1 INFECTED INDIVIDUALS
• Recent NIPH Clinical Trials: Effectiveness of Ezetimibe or Pitavastatin calcium calcium in NASH/NAFLD patients with high cholesterol levels: a randomized controlled study
• Description: Pitavastatin (Brand Name: LIVALO) is an inhibitor of HMG-CoA reductase which catalyzes the first step of cholesterol synthesis. It appears as odorless and white to pale-yellow powder. It takes effects by reducing the level of certain fatty substances such as cholesterol in the body. Therefore, it is mainly indicated for the treatment of hypercholesterolaemia and for the prevention of cardiovascular diseases. It can not only lower the high cholesterol and triglyceride in certain patients, but also can increase the content of high density lipoprotein (HDL), the “good” cholesterol levels. It should be generally administrated together with a proper diet.
• Uses: HMGA reductase inhibitor

Technology Process of (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid

There total 64 articles about (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid 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: 100.0%

methyl (3R,5S,6E)-7-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}-3,5-dihydroxyhept-6-enoate (849811-78-5) → pitavastatin (147526-32-7,147511-69-1,688735-41-3,769908-13-6,121659-03-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 0.5h;

DOI:10.1039/c4ob01953a

Reference yield: 95.9%

pitavastatin calcium salt (147526-32-7) → pitavastatin (147526-32-7,147511-69-1,688735-41-3,769908-13-6,121659-03-8)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; at 25 - 35 ℃;

Reference yield: 94.0%

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester (147489-06-3) → pitavastatin (147526-32-7,147511-69-1,688735-41-3,769908-13-6,121659-03-8)

Guidance literature:

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester; With trifluoroacetic acid; In acetonitrile; at 30 - 35 ℃;

With caesium carbonate; In acetonitrile; at 35 - 40 ℃;

upstream raw materials:

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (3S,5R,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>-3,5-dihydroxy-6-heptenoate

(±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

Refernces

• 1、 -. "Multi-substituted dihydroisoquinolines he the sandbank contains the fluorine derivative and use thereof". Paragraph 0135; 0136. . Retrieved 2018/06/04.
• 2、 -. "Method for preparing pitavastatin lactone impurity". Paragraph 0007. . Retrieved 2016/11/17.