Befetupitant

Base Information

• Chemical Name: Befetupitant
• CAS No.: 290296-68-3
• Molecular Formula: C29H29 F6 N3 O2
• Molecular Weight: 565.559
• UNII: RSH7NDI7MI
• DSSTox Substance ID: DTXSID90183270
• Nikkaji Number: J2.298.342C
• Wikipedia: Befetupitant
• Wikidata: Q27074983
• NCI Thesaurus Code: C78006
• Pharos Ligand ID: BN9U3ZAN5M2R
• ChEMBL ID: CHEMBL204694
• Mol file: 290296-68-3.mol

Synonyms:befetupitant

Chemical Property of Befetupitant

Chemical Property:

• Vapor Pressure: 2.39E-14mmHg at 25°C
• Melting Point: 128.8-129.9 °C
• Boiling Point: 599.8°Cat760mmHg
• PKA: 4.98±0.10(Predicted)
• Flash Point: 316.6°C
• PSA: 45.67000
• Density: 1.283g/cm³
• LogP: 6.93680
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 565.21639615
• Heavy Atom Count: 40
• Complexity: 838

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C2=CC(=NC=C2N(C)C(=O)C(C)(C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCOCC4
• Uses: Treatment of depression.

Technology Process of Befetupitant

There total 27 articles about Befetupitant 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:

N-methyl-N-[6-(morpholin-4-yl)-4-(o-tolyl)pyridin-3-yl]amine (290297-36-8) → 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide (290296-68-3)

Guidance literature:

With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride; dichloromethane;

Reference yield:

2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride (289686-69-7) + N-methyl-N-[6-(morpholin-4-yl)-4-(o-tolyl)pyridin-3-yl]amine (290297-36-8) → 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide (290296-68-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jo0523666

Reference yield:

2,2-dimethyl-N-(6-morpholin-4-yl-pyridin-3-yl)-propionamide (290297-32-4) → 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide (290296-68-3)

Guidance literature:

Multi-step reaction with 6 steps

1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / -78 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; toluene / 80 °C

3: hydrogenchloride / water; propan-1-ol / 95 °C

4: trifluoroacetic acid / 130 °C

5: lithium aluminium tetrahydride / tetrahydrofuran

6: N-ethyl-N,N-diisopropylamine / dichloromethane / 40 °C

With hydrogenchloride; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; propan-1-ol; dichloromethane; water; toluene; 2: |Suzuki Coupling;

DOI:10.1021/op060128m

upstream raw materials:

2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride

N-methyl-N-[6-(morpholin-4-yl)-4-(o-tolyl)pyridin-3-yl]amine

N-tert-butyl-6-(morpholin-4-yl)-nicotinamide

N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide

Refernces

• 1、 Harrington, Peter J.,Johnston, Dave,Moorlag, Henk,Wong, Jim-Wah,Hodges, L. Mark,Harris, Les,McEwen, Gerald K.,Smallwood, Blair. "Research and development of an efficient process for the construction of the 2,4,5-substituted pyridines of NK-1 receptor antagonists". . p. 1157 - 1166. Retrieved 2012/12/23.
• 2、 -. "Method of treatment and/or prevention of brain, spinal or nerve injury". . . Retrieved 2008/06/13.