Methyl (E)-3-[2-butyl-1-[(4-carbomethoxyphenyl)methyl]imidazol-5-YL]-2-(2-thienylmethyl)-2-propenoate

Base Information

• Chemical Name: Methyl (E)-3-[2-butyl-1-[(4-carbomethoxyphenyl)methyl]imidazol-5-YL]-2-(2-thienylmethyl)-2-propenoate
• CAS No.: 133040-06-9
• Molecular Formula: C25H28N2O4S
• Molecular Weight: 452.56582
• DSSTox Substance ID: DTXSID60439473
• Wikidata: Q82255428
• Mol file: 133040-06-9.mol

Synonyms:133040-06-9;METHYL (E)-3-[2-BUTYL-1-[(4-CARBOMETHOXYPHENYL)METHYL]IMIDAZOL-5-YL]-2-(2-THIENYLMETHYL)-2-PROPENOATE;Methyl 4-[[2-butyl-5-[(E)-3-methoxy-3-oxo-2-(thiophen-2-ylmethyl)prop-1-enyl]imidazol-1-yl]methyl]benzoate;Eprosartan Dimethyl Ester;SCHEMBL10052618;DTXSID60439473;J-006290

Chemical Property of Methyl (E)-3-[2-butyl-1-[(4-carbomethoxyphenyl)methyl]imidazol-5-YL]-2-(2-thienylmethyl)-2-propenoate

Chemical Property:

• Boiling Point: 613.3±55.0 °C(Predicted)
• PKA: 6.12±0.50(Predicted)
• PSA: 98.66000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 4.92120
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 452.17697855
• Heavy Atom Count: 32
• Complexity: 648

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl(E)-3-[2-Butyl-1-[(4-Carbomethoxyphenyl)methyl]imidazol-5-yl]-2-(2-thienylmethyl)-2-propenoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)OC)C=C(CC3=CC=CS3)C(=O)OC
• Isomeric SMILES: CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)OC)/C=C(\CC3=CC=CS3)/C(=O)OC
• Uses: Methyl (E)-3-[2-Butyl-1-[(4-Carbomethoxyphenyl)methyl]imidazol-5-yl]-2-(2-thienylmethyl)-2-propenoate (cas# 133040-06-9) is a compound useful in organic synthesis.

Technology Process of Methyl (E)-3-[2-butyl-1-[(4-carbomethoxyphenyl)methyl]imidazol-5-YL]-2-(2-thienylmethyl)-2-propenoate

There total 14 articles about Methyl (E)-3-[2-butyl-1-[(4-carbomethoxyphenyl)methyl]imidazol-5-YL]-2-(2-thienylmethyl)-2-propenoate 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: 40.0%

monomethyl (2-theinyl)malonate + 2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde (133040-03-6) → methyl (E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenoate (133040-06-9)

Guidance literature:

With piperidine; pyridine; In toluene;

DOI:10.1021/jm00108a043

Reference yield:

Methyl 4-(bromomethyl)benzoate (2417-72-3) → methyl (E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenoate (133040-06-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / K₂CO₃ / dimethylformamide / 17 h / 80 °C

2: 96 percent / H₂, NaOAc / 10percent Pd/C / methanol / 18 h

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, 30 min

4: DMAP / CH₂Cl₂ / 2 h / Ambient temperature

5: DBU / toluene / 3 h / 80 °C

With dmap; hydrogen; sodium acetate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1080/00397919308011184

Reference yield:

4-[5-(1-Acetoxy-2-methoxycarbonyl-3-thiophen-2-yl-propyl)-2-butyl-imidazol-1-ylmethyl]-benzoic acid methyl ester (133040-05-8) → methyl (E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenoate (133040-06-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 80 ℃; for 3h; Yield given;

DOI:10.1080/00397919308011184

upstream raw materials:

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde

4-[5-(1-Acetoxy-2-methoxycarbonyl-3-thiophen-2-yl-propyl)-2-butyl-imidazol-1-ylmethyl]-benzoic acid methyl ester

2-butyl-1H-imidazole

Methyl 4-(bromomethyl)benzoate

Downstream raw materials:

eprosartan

4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzonitrile

(E)-3-<2-butyl-1-<(4-carboxamidophenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenamide

SB 206328