Anacetrapib

Base Information

• Chemical Name: Anacetrapib
• CAS No.: 875446-37-0
• Molecular Formula: C30H25F10NO3
• Molecular Weight: 637.517
• European Community (EC) Number: 810-468-5
• UNII: P7T269PR6S
• ChEMBL ID: CHEMBL1800807
• DSSTox Substance ID: DTXSID90236452
• Metabolomics Workbench ID: 149870
• NCI Thesaurus Code: C75251
• Nikkaji Number: J2.620.043A
• Pharos Ligand ID: U4RN9W5YMRGL
• Wikidata: Q4750639
• Wikipedia: Anacetrapib
• Mol file: 875446-37-0.mol

Synonyms:anacetrapib;MK 0859;MK-0859;MK0859

Chemical Property of Anacetrapib

Chemical Property:

• Boiling Point: 555.309 °C at 760 mmHg
• PKA: -2.30±0.60(Predicted)
• Flash Point: 289.641 °C
• PSA: 38.77000
• Density: 1.345 g/cm³
• LogP: 9.70100
• Solubility.: ≥31.9 mg/mL in DMSO; insoluble in H2O; ≥86.6 mg/mL in EtOH
• XLogP3: 8.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 637.16747528
• Heavy Atom Count: 44
• Complexity: 964

Purity/Quality:

Anacetrapib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(=O)N1CC2=C(C=CC(=C2)C(F)(F)F)C3=CC(=C(C=C3OC)F)C(C)C)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F
• Isomeric SMILES: C[C@H]1[C@H](OC(=O)N1CC2=C(C=CC(=C2)C(F)(F)F)C3=CC(=C(C=C3OC)F)C(C)C)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F
• Recent ClinicalTrials: The Effect of Anacetrapib on Vascular Function and Arterial Stiffness
• Recent EU Clinical Trials: A Worldwide, Multicenter, Double-Blind, Randomized, Placebo-Controlled, 12-Week Study to Assess the Efficacy and Tolerability of Anacetrapib When Added to Ongoing Lipid-Lowering Therapy in Adult Patients with Homozygous Familial Hypercholesterolemia (HoFH) with a 52-Week Open-Label Extension
• Uses: An orally active and potent cholesterol ester transfer protein (CETP) inhibitor for the treatment of atherosclerosis, in particular dyslipidemia.

Technology Process of Anacetrapib

There total 42 articles about Anacetrapib 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: 92.0%

2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl (875551-28-3) + (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (875444-08-9) → anacetrapib (875446-37-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 17h;

Reference yield: 89.0%

C37H33F10NO4 → anacetrapib (875446-37-0)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; Inert atmosphere;

Reference yield: 88.0%

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one + 2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl (875551-28-3) → anacetrapib (875446-37-0)

Guidance literature:

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one; With sodium hexamethyldisilazane; In N,N-dimethyl-formamide; at -15 ℃; for 1.5h;

2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl; In N,N-dimethyl-formamide; at -15 - 12 ℃;

upstream raw materials:

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]boronic acid

2'-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

Downstream raw materials:

(1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-[({2-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]-5-(trifluoromethyl)phenyl}methyl)amino]propan-1-ol

(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((4'-fluoro-5'-isopropyl-2'-hydroxy-4-(trifluoromethyl)biphenyl-2-yl)methyl)-4-methyl-1,3-oxazolidin-2-one

Refernces

• 1、 -. "Preparation method of Anacetrapib". . . Retrieved 2017/08/28.
• 2、 -. "CATALYST AND METHOD FOR PRODUCING OPTICALLY ACTIVE ANTI-1,2-NITROALKANOL COMPOUND". . . Retrieved 2016/01/12.