8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester

Base Information

• Chemical Name: 8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester
• CAS No.: 167853-94-3
• Molecular Formula: C₂₆H₂₂N₄O₃
• Molecular Weight: 438.486
• Mol file: 167853-94-3.mol

Synonyms:8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester

Chemical Property of 8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester

There total 11 articles about 8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester 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: 78.0%

4-cyanophenylacetylene (3032-92-6) + 8-iodo-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester (167853-93-2) → 8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester (167853-94-3)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In ethyl acetate; at 20 ℃;

DOI:10.1016/S0968-0896(98)80013-8

Reference yield:

ethyl β-alaninate hydrochloride (4244-84-2) → 8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester (167853-94-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / triethylamine; DMAP / dimethylformamide

2: 56 percent / 2,6-lutidine / dimethylformamide / 1 h / 50 °C

3: CH₂Cl₂; H₂O / 20 °C

4: 474 mg / sodium hydride / dimethylformamide / 2 h / 0 - 10 °C

5: 80 percent / ethyl methyl sulfide; hydrogen fluoride / methoxybenzene / 2 h / -196 °C

6: 91 percent / Lawesson's reagent / tetrahydrofuran / 2 h / 50 °C

7: 82 percent / tetrabutylammonium hydrogen sulfate; sodium hydroxide / CH₂Cl₂; H₂O / 16 h / 20 °C

8: 66 percent / pyridinium hydrochloride / toluene / 5 h / Heating

9: 78 percent / copper iodide; triethylamine / bis(triphenylphosphine)palladium dichloride / ethyl acetate / 20 °C

With Lawessons reagent; 2,6-dimethylpyridine; dmap; sodium hydroxide; copper(l) iodide; Ethyl methyl sulfide; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; pyridine hydrochloride; sodium hydride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; water; ethyl acetate; methoxybenzene; N,N-dimethyl-formamide; toluene; 1: Acylation / 2: Alkylation / 3: Acylation / 4: Cyclization / 5: deprotection / 6: Substitution / 7: Methylation / 8: Cyclization / 9: Heck coupling;

DOI:10.1016/S0968-0896(98)80013-8

Reference yield:

5-iodoisatoic anhydride (116027-10-2) → 8-[[4-cyanophenyl]ethynyl]-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester (167853-94-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / triethylamine; DMAP / dimethylformamide

2: 56 percent / 2,6-lutidine / dimethylformamide / 1 h / 50 °C

3: CH₂Cl₂; H₂O / 20 °C

4: 474 mg / sodium hydride / dimethylformamide / 2 h / 0 - 10 °C

5: 80 percent / ethyl methyl sulfide; hydrogen fluoride / methoxybenzene / 2 h / -196 °C

6: 91 percent / Lawesson's reagent / tetrahydrofuran / 2 h / 50 °C

7: 82 percent / tetrabutylammonium hydrogen sulfate; sodium hydroxide / CH₂Cl₂; H₂O / 16 h / 20 °C

8: 66 percent / pyridinium hydrochloride / toluene / 5 h / Heating

9: 78 percent / copper iodide; triethylamine / bis(triphenylphosphine)palladium dichloride / ethyl acetate / 20 °C

With Lawessons reagent; 2,6-dimethylpyridine; dmap; sodium hydroxide; copper(l) iodide; Ethyl methyl sulfide; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; pyridine hydrochloride; sodium hydride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; water; ethyl acetate; methoxybenzene; N,N-dimethyl-formamide; toluene; 1: Acylation / 2: Alkylation / 3: Acylation / 4: Cyclization / 5: deprotection / 6: Substitution / 7: Methylation / 8: Cyclization / 9: Heck coupling;

DOI:10.1016/S0968-0896(98)80013-8

upstream raw materials:

4-cyanophenylacetylene

8-iodo-1-methyl-6-oxo-4H-imidazo[1,2-a][1,4]benzodiazepine-5(6H)-propanoic acid ethyl ester

ethyl β-alaninate hydrochloride

5-iodoisatoic anhydride