Maropitant

Base Information

• Chemical Name: Maropitant
• CAS No.: 147116-67-4
• Molecular Formula: C32H40N2O
• Molecular Weight: 468.682
• European Community (EC) Number: 831-973-7
• UNII: 4XE2T9H4DH
• DSSTox Substance ID: DTXSID1057874
• Nikkaji Number: J2.504.460F
• Wikipedia: Maropitant
• Wikidata: Q3849795
• NCI Thesaurus Code: C81500
• Metabolomics Workbench ID: 152625
• ChEMBL ID: CHEMBL2111099
• Mol file: 147116-67-4.mol

Synonyms:(2S,2S)-2-benzhydryl-N-(5-tert-butyl-2-methoxybenzyl)quinuclidin-3-amine citrate monohydrate;(2S,3S)-2-benzhydryl-N-(5-(tert-butyl)-2-methoxybenzyl)quinuclidin-3-amine 2-hydroxypropane-1,2,3-tricarboxylate hydrate;(2S,3S)-2-benzhydryl-N-(5-tert-butyl-2-methoxybenzyl)quinuclidin-3-amine citrate monohydrate;2-benzhydryl-N-(5-tert-butyl-2-methoxybenzyl)quinuclidin-3-amine citrate monohydrate;maropitant;maropitant citrate

Chemical Property of Maropitant

Chemical Property:

• Vapor Pressure: 4.05E-13mmHg at 25°C
• Boiling Point: 572.6°C at 760 mmHg
• PKA: 9.99±0.70(Predicted)
• Flash Point: 300.1°C
• PSA: 24.50000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 6.70600
• XLogP3: 7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 468.314063904
• Heavy Atom Count: 35
• Complexity: 620

Purity/Quality:

99.9% ^*data from raw suppliers

Maropitant >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=C(C=C1)OC)CNC2C3CCN(C2C(C4=CC=CC=C4)C5=CC=CC=C5)CC3
• Isomeric SMILES: CC(C)(C)C1=CC(=C(C=C1)OC)CN[C@@H]2[C@@H](N3CCC2CC3)C(C4=CC=CC=C4)C5=CC=CC=C5
• Uses: Maropitant is a neurokinin type 1 (NK-1) receptor antagonist. Recent studies show that Maropitant decreased the anesthetic requirements during visceral stimulation of the ovary and ovarian ligament in dogs.

Technology Process of Maropitant

There total 13 articles about Maropitant 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: 87.1%

(2S,3R)-2-diphenylmethyl-3-methanesulfonyloxyquinuclidine + 2-methoxy-5-tert-butylbenzylamine (1226409-70-6) → (2S,3S)-N-(5-tert-butyl-2-methoxyphenyl)methyl-2-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-amine (147116-67-4)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 100 ℃;

Reference yield: 85.3%

2-(bromomethyl)-4-(tert-butyl)-1-methoxybenzene (911060-73-6) + (-)-(2S,3S)-cis-2-(diphenylmethyl)-1-azabicyclo[2.2.2]octane-3-amine (142035-23-2) → (2S,3S)-N-(5-tert-butyl-2-methoxyphenyl)methyl-2-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-amine (147116-67-4)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; at 0 - 30 ℃;

Reference yield: 82.6%

2-methoxy-5-tert-butylbenzylamine (1226409-70-6) + (2S,3R)-2-diphenylmethyl-3-trifluoromethanesulfonyloxyquinuclidine → (2S,3S)-N-(5-tert-butyl-2-methoxyphenyl)methyl-2-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-amine (147116-67-4)

Guidance literature:

With dmap; In 2-methyltetrahydrofuran; Reflux;

upstream raw materials:

(2S,3S)-2-benzhydryl-N-(5-tert-butyl-2-methoxybenzyl)quinuclidin-3-amine (1R)-10-camphorsulfonate

methyl 3-oxoquinuclidine-2-carboxylate

2-(bromomethyl)-4-(tert-butyl)-1-methoxybenzene

(-)-(2S,3S)-cis-2-(diphenylmethyl)-1-azabicyclo[2.2.2]octane-3-amine

Downstream raw materials:

maropitant citrate monohydrate

maropitant citrate