Torcetrapib

Base Information

• Chemical Name: Torcetrapib
• CAS No.: 262352-17-0
• Molecular Formula: C26H25F9N2O4
• Molecular Weight: 600.481
• European Community (EC) Number: 689-436-6
• UNII: 4N4457MV2U
• DSSTox Substance ID: DTXSID20180873
• Nikkaji Number: J1.996.201F
• Wikipedia: Torcetrapib
• Wikidata: Q7825530
• NCI Thesaurus Code: C91058
• Pharos Ligand ID: W2Q7B1WF6UTQ
• Metabolomics Workbench ID: 57254
• ChEMBL ID: CHEMBL479527
• Mol file: 262352-17-0.mol

Synonyms:(2R,4S)-4-[(3,5-Bis-trifluoromethylbenzyl)methoxycarbonylamino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylicacid ethyl ester;(2R,4S)-4-[[3,5-Bis(trifluoromethyl)benzyl]methoxycarbonylamino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylicacid ethyl ester;CP 529414;(-)-Torcetrapib;1(2H)-Quinolinecarboxylicacid,4-[[[3,5-bis(trifluoromethyl)phenyl]methyl](methoxycarbonyl)amino]-2-ethyl-3,4-dihydro-6-(trifluoromethyl)-,ethyl ester, (2R,4S)-;

Chemical Property of Torcetrapib

Chemical Property:

• Appearance/Colour: lipid
• Vapor Pressure: 2.58E-10mmHg at 25°C
• Melting Point: 54-58 °C
• Refractive Index: 1.511
• Boiling Point: 504.8 °C at 760 mmHg
• Flash Point: 259.1 °C
• PSA: 59.08000
• Density: 1.42 g/cm³
• LogP: 8.26290
• XLogP3: 7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 600.16706074
• Heavy Atom Count: 41
• Complexity: 889

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CC(C2=C(N1C(=O)OCC)C=CC(=C2)C(F)(F)F)N(CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C(=O)OC
• Isomeric SMILES: CC[C@@H]1C[C@@H](C2=C(N1C(=O)OCC)C=CC(=C2)C(F)(F)F)N(CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C(=O)OC
• Recent EU Clinical Trials: Phase 3 multi center, double blind, randomized, parallel group evaluation of the fixed combination torcetrapib/atorvastatin, administered orally, once daily (QD), compared with atorvastatin alone, on the occurrence of major cardiovascular events in subjects with coronary heart disease or risk equivalents.

Technology Process of Torcetrapib

There total 16 articles about Torcetrapib 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: 74.0%

(-)-(2R,4S)-4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester tosylate salt + methyl chloroformate (79-22-1) → torcetrapib (262352-17-0)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/op060014a

Reference yield:

4-trifluoromethylphenylamine (455-14-1) → torcetrapib (262352-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: (S)-P-Phos / Pd(OTf)2*2H₂O / toluene / 36 h / 50 °C

2: 92 percent / sodium borohydride; MgCl₂*6H₂O / ethanol; H₂O / -10 - 0 °C

3: 82 percent / pyridine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

4: 52 percent / potassium tert-butoxide / CH₂Cl₂ / 4 h / 20 °C

With pyridine; sodium tetrahydroborate; (S)-P-Phos; potassium tert-butylate; magnesium chloride; bis(trifluoromethyl sulfate)palladium; In ethanol; dichloromethane; water; toluene; 1: aza-Michael reaction;

DOI:10.1021/jo071031g

Reference yield:

(E)-pent-2-enoyl-carbamic acid methyl ester (948847-52-7) → torcetrapib (262352-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: (S)-P-Phos / Pd(OTf)2*2H₂O / toluene / 36 h / 50 °C

2: 92 percent / sodium borohydride; MgCl₂*6H₂O / ethanol; H₂O / -10 - 0 °C

3: 82 percent / pyridine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

4: 52 percent / potassium tert-butoxide / CH₂Cl₂ / 4 h / 20 °C

With pyridine; sodium tetrahydroborate; (S)-P-Phos; potassium tert-butylate; magnesium chloride; bis(trifluoromethyl sulfate)palladium; In ethanol; dichloromethane; water; toluene; 1: aza-Michael reaction;

DOI:10.1021/jo071031g

upstream raw materials:

(3R)-[3-(4-trifluoromethylphenylamino)pentanoyl]carbamic acid methyl ester

(2R,4S)-(2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamic acid methyl ester

(E)-pent-2-enoyl-carbamic acid methyl ester

4-trifluoromethylphenylamine

Refernces

• 1、 Guino, Meritxell,Pim, Huat Phua,Caille, Jean-Claude,King, Kuok Hii. "A concise asymmetric synthesis of torcetrapib". . p. 6290 - 6293. Retrieved 2008/02/10.
• 2、 -. "CETP inhibitors in combination with antihypertensive agents and uses thereof". . . Retrieved 2008/06/13.