3-methyl-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

Base Information

• Chemical Name: 3-methyl-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide
• CAS No.: 174635-69-9
• Molecular Formula: C26H24N2O
• Molecular Weight: 380.4816
• DSSTox Substance ID: DTXSID90938540
• Nikkaji Number: J750.056D
• Wikidata: Q27088710
• Pharos Ligand ID: WDR6DPGUM87P
• ChEMBL ID: CHEMBL10284
• Mol file: 174635-69-9.mol

Synonyms:N-(alpha-ethylbenzyl)-3-methyl-2-phenylquinoline-4-carboxamide;SB 222200;SB-222200

Chemical Property of 3-methyl-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

Chemical Property:

• Vapor Pressure: 2.7E-12mmHg at 25°C
• Melting Point: 154℃
• Boiling Point: 553.5°Cat760mmHg
• PKA: 12.88±0.46(Predicted)
• Flash Point: 288.6°C
• PSA: 41.99000
• Density: 1.142g/cm³
• LogP: 6.48220
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~28 mg/mL, soluble
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 380.188863393
• Heavy Atom Count: 29
• Complexity: 523

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

3-Methyl-2-phenyl-N-[(1S)-1-phenylpropyl]-4-quinolinecarboxamide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1=CC=CC=C1)NC(=O)C2=C(C(=NC3=CC=CC=C32)C4=CC=CC=C4)C
• Isomeric SMILES: CC[C@@H](C1=CC=CC=C1)NC(=O)C2=C(C(=NC3=CC=CC=C32)C4=CC=CC=C4)C
• Uses: 3-Methyl-2-phenyl-N-[(1S)-1-phenylpropyl]-4-quinolinecarboxamide is a chemical agent used in the preparation of acylpiperazinyl-pyrazoles as antagonists to the NK3 receptor as antipsychotics (1,2).

Technology Process of 3-methyl-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

There total 11 articles about 3-methyl-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide 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: 25.0%

hexamethyldistannane (661-69-8) + (S)-N-(1-phenylpropyl)-3-bromo-2-phenylquinoline-4-carboxamide (174636-18-1) → 2-phenyl-4-(carboxy-(S)-α-ethylbenzylamine)quinoline (174636-20-5) + (-)-(S)-N-(α-ethylbenzyl)-3-methyl-2-phenylquinoline-4-carboxamide (174635-69-9)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; for 72h; Heating;

DOI:10.1021/jo062285p

Reference yield:

2-phenyl-4-(carboxy-(S)-α-ethylbenzylamine)quinoline (174636-20-5) + methyl iodide (74-88-4) → (-)-(S)-N-(α-ethylbenzyl)-3-methyl-2-phenylquinoline-4-carboxamide (174635-69-9)

Guidance literature:

2-phenyl-4-(carboxy-(S)-α-ethylbenzylamine)quinoline; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -60 ℃; for 5h;

With trimethyltin(IV)chloride; In tetrahydrofuran; hexane; at -60 ℃; for 1h;

methyl iodide; With potassium carbonate; tris-(o-tolyl)phosphine; copper(l) chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In N,N-dimethyl-formamide; at 90 ℃; for 24h;

DOI:10.1021/jo062285p

Reference yield:

2-phenyl-4-(carboxy-(S)-α-ethylbenzylamine)quinoline (174636-20-5) + methyl iodide (74-88-4) → 3-methyl-2-phenyl-quinoline-4-carboxylic acid methyl-(1-phenyl-propyl)-amide + (-)-(S)-N-(α-ethylbenzyl)-3-methyl-2-phenylquinoline-4-carboxamide (174635-69-9)

Guidance literature:

2-phenyl-4-(carboxy-(S)-α-ethylbenzylamine)quinoline; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -60 ℃; for 5h;

With trimethyltin(IV)chloride; In tetrahydrofuran; hexane; at -60 ℃; for 1h;

methyl iodide; With potassium carbonate; tris-(o-tolyl)phosphine; copper(l) chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In N,N-dimethyl-formamide; at 90 ℃; for 24h;

DOI:10.1021/jo062285p

upstream raw materials:

3-methyl-2-phenylquinoline-4-carboxylic acid

(R)-1-phenylpropylamine

3-methyl-2-phenylquinoline-4-carbonyl chloride

hexamethyldistannane

Refernces

• 1、 Giardina, Giuseppe A. M.,Raveglia, Luca F.,Grugni, Mario,Sarau, Henry M.,Farina, Carlo,Medhurst, Andrew D.,Graziani, Davide,Schmidt, Dulcie B.,Rigolio, Roberto,Luttmann, Mark,Cavagnera, Stefano,Foley, James J.,Vecchietti, Vittorio,Hay, Douglas W. P.. "Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 2. Identification of (S)-N-(1-phenylpropyl)-3- hydroxy-2-phenylquinoline-4-carboxamide (SB 223412)". . p. 1053 - 1065. Retrieved 2007/10/03.