5-(4-Methoxyphenyl)-N-(1-methyl-4-(3-pyridinyl)butyl)-2,4-decadienamide

Base Information

• Chemical Name: 5-(4-Methoxyphenyl)-N-(1-methyl-4-(3-pyridinyl)butyl)-2,4-decadienamide
• CAS No.: 120555-31-9
• Molecular Formula: C27H36 N2 O2
• Molecular Weight: 420.59
• UNII: 7G3UI0W9Y5
• Nikkaji Number: J347.591C
• Pharos Ligand ID: 6RVLRKPKLNLV
• ChEMBL ID: CHEMBL277245
• Mol file: 120555-31-9.mol

Synonyms:5-(4-methoxyphenyl)-N-(1-methyl-4-(3-pyridinyl)butyl)-2,4-decadienamide;Ro 24-0238;Ro-24-0238

Chemical Property of 5-(4-Methoxyphenyl)-N-(1-methyl-4-(3-pyridinyl)butyl)-2,4-decadienamide

Chemical Property:

• Vapor Pressure: 1.21E-15mmHg at 25°C
• Melting Point: 88-89 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• Boiling Point: 627.1°Cat760mmHg
• PKA: 14.07±0.46(Predicted)
• Flash Point: 333.1°C
• PSA: 51.22000
• Density: 1.026g/cm³
• LogP: 6.52860
• XLogP3: 7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 420.277678395
• Heavy Atom Count: 31
• Complexity: 549

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=CC=CC(=O)NC(C)CCCC1=CN=CC=C1)C2=CC=C(C=C2)OC
• Isomeric SMILES: CCCCC/C(=C\C=C\C(=O)N[C@H](C)CCCC1=CN=CC=C1)/C2=CC=C(C=C2)OC

Technology Process of 5-(4-Methoxyphenyl)-N-(1-methyl-4-(3-pyridinyl)butyl)-2,4-decadienamide

There total 23 articles about 5-(4-Methoxyphenyl)-N-(1-methyl-4-(3-pyridinyl)butyl)-2,4-decadienamide 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: 92.7%

(R)-α-methyl-3-pyridinebutanamine (111954-72-4) + (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid 4-nitrophenyl ester (120554-77-0) → Ro 24-0238 (120555-31-9)

Guidance literature:

In tetrahydrofuran; 1.) room temperature, overnight, 2.) reflux, 3 h;

DOI:10.1021/jm00128a026

Reference yield:

3-pyridinecarboxylic acid ethyl ester (614-18-6) → Ro 24-0238 (120555-31-9)

Guidance literature:

Multi-step reaction with 10 steps

1: NaOMe / propan-2-ol / 1 h / Heating

2: 3 N H₂SO₄ / Heating

3: NH₂NH₂*H₂O / bis-(2-hydroxy-ethyl) ether / 1.5 h / 140 - 150 °C

4: KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 140 - 150 °C

5: 84 percent / 3 h / 40 - 50 °C

7: K₂CO₃ / methanol

8: 201.7 g / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9: NaN₃ / dimethylformamide / 2.5 h / 70 °C

10: 537 mg / n-Bu₃P / cyclohexane / 20 h / Heating

With potassium hydroxide; sodium azide; tributylphosphine; sulfuric acid; sodium methylate; potassium carbonate; hydrazine hydrate; triethylamine; In methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; isopropyl alcohol; diethylene glycol;

Reference yield:

alpha-methyl-3-pyridinebutanol (119981-04-3) → Ro 24-0238 (120555-31-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / 3 h / 40 - 50 °C

3: K₂CO₃ / methanol

4: 201.7 g / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: NaN₃ / dimethylformamide / 2.5 h / 70 °C

6: 537 mg / n-Bu₃P / cyclohexane / 20 h / Heating

With sodium azide; tributylphosphine; potassium carbonate; triethylamine; In methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide;

upstream raw materials:

(R)-α-methyl-3-pyridinebutanamine

(E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid 4-nitrophenyl ester

(R)-3-(4-azidopentyl)pyridine

(E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid

Refernces

• 1、 Guthrie,Kaplan,Mennona,Tilley,Kierstead,Mullin,LeMahieu,Zawoiski,O'Donnell,Crowley,Yaremko,Welton. "Pentadienyl carboxamide derivatives as antagonists of platelet-activating factor". . p. 1820 - 1835. Retrieved 2007/10/02.