Vicriviroc

Base Information

• Chemical Name: Vicriviroc
• CAS No.: 306296-47-9
• Molecular Formula: C₂₈H₃₈F₃N₅O₂
• Molecular Weight: 533.637
• UNII: TL515DW4QS
• DSSTox Substance ID: DTXSID40897719
• Nikkaji Number: J1.905.357A
• Wikipedia: Vicriviroc
• Wikidata: Q3557001
• NCI Thesaurus Code: C73589
• Pharos Ligand ID: 9NCBGUWKMNJH
• Metabolomics Workbench ID: 149882
• ChEMBL ID: CHEMBL82301
• Mol file: 306296-47-9.mol

Synonyms:1-((4,6-dimethyl-5-pyrimidinyl)carbonyl)-4-(4-(2-methoxy-4-(trifluoromethyl)phenyl)ethyl-3-methyl-1-piperazinyl)-4-methylpiperidine;Sch 417690;Sch-417690;Sch417690;vicriviroc

Chemical Property of Vicriviroc

Chemical Property:

• Vapor Pressure: 9.89E-15mmHg at 25°C
• Boiling Point: 608.1°Cat760mmHg
• PKA: 7.61±0.70(Predicted)
• Flash Point: 321.5°C
• PSA: 61.80000
• Density: 1.196g/cm³
• LogP: 4.31440
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 533.29775996
• Heavy Atom Count: 38
• Complexity: 773

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CN(CCN1C(COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C
• Isomeric SMILES: C[C@H]1CN(CCN1[C@@H](COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C
• Recent ClinicalTrials: Vicriviroc in HIV-Treatment Experienced Subjects (Study P04889AM8)(COMPLETED)
• Recent EU Clinical Trials: COVER- Registro de observación continua tras exposición Vicriviroc (VCV)

Technology Process of Vicriviroc

There total 9 articles about Vicriviroc 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: 93.0%

4,6-dimethylpyrimidine-5-carboxylic acid (157335-93-8) + (S)-1-[(R)-2-Methoxy-1-(4-trifluoromethyl-phenyl)-ethyl]-2-methyl-4-(4-methyl-piperidin-4-yl)-piperazine (696601-20-4) → vicriviroc (306296-47-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jm0304515

Reference yield:

2-methoxy-1-(4-(trifluoromethyl)phenyl)ethan-1-one (26771-69-7) → vicriviroc (306296-47-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: borane dimethylsulfide; (S)-2-methyl-CBS-oxaborolidine / 1 h

2.1: triethylamine / CH₂Cl₂ / 0.5 h / cooling

3.1: 14.8 g / K₂CO₃ / acetonitrile / 72 h / Heating

4.1: 7.9 g / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

5.1: Ti(OiPr)4 / CH₂Cl₂ / 20 h / 20 °C

5.2: 13.4 g / CH₂Cl₂; toluene / 20 h

6.1: 76 percent / tetrahydrofuran / 48 h / 20 °C

7.1: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 6 h / 20 °C

8.1: 93 percent / diisopropylethyl amine; EDCl; HOBt / CH₂Cl₂ / 24 h / 20 °C

With titanium(IV) isopropylate; dimethylsulfide borane complex; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jm0304515

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → vicriviroc (306296-47-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Ti(OiPr)4 / CH₂Cl₂ / 20 h / 20 °C

1.2: 13.4 g / CH₂Cl₂; toluene / 20 h

2.1: 76 percent / tetrahydrofuran / 48 h / 20 °C

3.1: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 6 h / 20 °C

4.1: 93 percent / diisopropylethyl amine; EDCl; HOBt / CH₂Cl₂ / 24 h / 20 °C

With titanium(IV) isopropylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0304515

upstream raw materials:

4,6-dimethylpyrimidine-5-carboxylic acid

(S)-1-[(R)-2-Methoxy-1-(4-trifluoromethyl-phenyl)-ethyl]-2-methyl-4-(4-methyl-piperidin-4-yl)-piperazine

2-methoxy-1-(4-(trifluoromethyl)phenyl)ethan-1-one

N-tert-butyloxycarbonylpiperidin-4-one

Refernces

• 1、 Tagat, Jayaram R.,McCombie, Stuart W.,Nazareno, Dennis,Labroli, Marc A.,Xiao, Yushi,Steensma, Ruo W.,Strizki, Julie M.,Baroudy, Bahige M.,Cox, Kathleen,Lachowicz, Jean,Varty, Geoffrey,Watkins, Robert. "Piperazine-Based CCR5 Antagonists as HIV-1 Inhibitors. IV. Discovery of 1-[(4,6-Dimethyl-5-pyrimidinyl) carbonyl]-4-[4-{2-methoxy-1(R)-4-(trifluoromethyl)-phenyl}ethyl-3(S) -methyl-1-piperazinyl]-4-methylpiperidine (Sch-417690/Sch-D), a Potent, Highly Sel". . p. 2405 - 2408. Retrieved 2007/10/03.