(2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

Base Information

• Chemical Name: (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal
• CAS No.: 1187383-65-8
• Molecular Formula: C₄₆H₅₅N₅O₇S₂
• Molecular Weight: 854.104
• Mol file: 1187383-65-8.mol

Synonyms:(2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property of (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

There total 9 articles about (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 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: 73.0%

4-{2-[4-(benzyloxy)phenyl]benzimidazol-6-yl}morpholine (1187383-72-7) + (2S)-N-[4-(5-bromopentyloxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal (343308-57-6) → (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal (1187383-65-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

Reference yield:

5-chloro-2-nitroaniline (1635-61-6) → (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal (1187383-65-8)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C

2: palladium 10% on activated carbon; hydrogen

3: sodium metabisulfite / ethanol; water / 4 h

4: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

With sodium metabisulfite; palladium 10% on activated carbon; hydrogen; potassium carbonate; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.2174/1573406411309050004

Reference yield:

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → (2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal (1187383-65-8)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / acetone / 48 h / Reflux

2: tin(IV) chloride; nitric acid / dichloromethane / 0.08 h / -25 °C

3: lithium hydroxide; methanol / water; tetrahydrofuran / 12 h / 20 °C

4: thionyl chloride; triethylamine / water; N,N-dimethyl-formamide; tetrahydrofuran; benzene / 6 h / 20 °C

5: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

With methanol; thionyl chloride; nitric acid; tin(IV) chloride; potassium carbonate; triethylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.2174/1573406411309050004

upstream raw materials:

4-{2-[4-(benzyloxy)phenyl]benzimidazol-6-yl}morpholine

(2S)-N-[4-(5-bromopentyloxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

5-chloro-2-nitroaniline

4-hydroxy-3-methoxybenzoic acid methyl ester

Downstream raw materials:

(2S)-N-{4-(5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal

7-methoxy-8-{5-[2-[(4-(benzyloxy)phenyl)-6-morpholino]benzimidazol-1-yl]pentyl}oxy-(11aS)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one