Rolapitant

Base Information

• Chemical Name: Rolapitant
• CAS No.: 552292-08-7
• Molecular Formula: C25H26F6N2O2
• Molecular Weight: 500.484
• European Community (EC) Number: 812-147-5
• UNII: NLE429IZUC
• DSSTox Substance ID: DTXSID90203740
• Wikipedia: Rolapitant
• NCI Thesaurus Code: C97952
• RXCUI: 1665496
• Pharos Ligand ID: GTVGUCU2W738
• Metabolomics Workbench ID: 152314
• ChEMBL ID: CHEMBL3707331
• Mol file: 552292-08-7.mol

Synonyms:(5S,8S)-8-(((1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-8-phenyl-1,7-diazaspiro(4.5)decan-2-one;8-((1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-8-phenyl-1,7-diazaspiro(4,5)decan-2-one;rolapitant;SCH 619734;Varubi

Chemical Property of Rolapitant

Chemical Property:

• Boiling Point: 523.5±50.0 °C(Predicted)
• PKA: 15.88±0.40(Predicted)
• PSA: 50.36000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 6.38710
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 500.18984705
• Heavy Atom Count: 35
• Complexity: 731

Purity/Quality:

98%, ^*data from raw suppliers

Rolapitant >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OCC2(CCC3(CCC(=O)N3)CN2)C4=CC=CC=C4
• Isomeric SMILES: C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OC[C@]2(CC[C@]3(CCC(=O)N3)CN2)C4=CC=CC=C4
• Recent ClinicalTrials: Rolapitant as an Antiemetic in Malignant Glioma Patients Receiving Radiotherapy and Temozolomide
• Recent EU Clinical Trials: A Phase 3, Multicenter, Randomized, Double-Blind, Active-Controlled Study of the Safety and Efficacy of Rolapitant for the Prevention of Chemotherapy-Induced Nausea and Vomiting (CINV) in Subjects Receiving Highly Emetogenic Chemotherapy (HEC)

Technology Process of Rolapitant

There total 32 articles about Rolapitant 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: 92.9%

C42H44F6N2O5 → Rolapitant (552292-08-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; under 3800.26 Torr; Autoclave; Large scale;

Reference yield: 92.6%

(S)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane (1297609-87-0) + (5S,8S)-8-hydroxymethyl-8-phenyl-1,7-diazaspiro[4.5]nonan-2-one → Rolapitant (552292-08-7)

Guidance literature:

(5S,8S)-8-hydroxymethyl-8-phenyl-1,7-diazaspiro[4.5]nonan-2-one; With sodium hydride; In N,N-dimethyl acetamide; at 0 - 5 ℃; for 0.5h;

(S)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane; In N,N-dimethyl acetamide;

Reference yield: 90.0%

(S)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane (1297609-87-0) + (5S,8S)-8-hydroxymethyl-8-phenyl-7-trifluoroacetyl-1,7-diazaspiro[4.5]nonan-2-one → Rolapitant (552292-08-7)

Guidance literature:

(5S,8S)-8-hydroxymethyl-8-phenyl-7-trifluoroacetyl-1,7-diazaspiro[4.5]nonan-2-one; With sodium hydride; In N,N-dimethyl acetamide; at 0 - 5 ℃; for 0.5h;

(S)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane; In N,N-dimethyl acetamide;

upstream raw materials:

methyl 3-[(3S,6S)-6-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)-3-nitro-6-phenylpiperidin-3-yl]propanoate methylsulfonate

C₃₆H₄₀F₆N₂O₆

C₃₀H₂₇F₆NO₄

Downstream raw materials:

(5S,8S)-8-[{(1R)-1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diazaspiro[4.5]decan-2-one maleate

(5S,8S)-8-[{(1R)-1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diazaspiro[4.5]decan-2-one mesylate

(5S,8S)-8-[{(1R)-1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diazaspiro[4.5]decan-2-one oxalate

(5S,8S)-8-[{(1R)-1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diazaspiro[4.5]decan-2-one esylate