benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Base Information

• Chemical Name: benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
• CAS No.: 1190363-63-3
• Molecular Formula: C₂₅H₃₄N₄O₄Si
• Molecular Weight: 482.655
• Mol file: 1190363-63-3.mol

Synonyms:benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Chemical Property of benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

There total 2 articles about benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate 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: 87.0%

benzyl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (1146637-16-2) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (1190363-63-3)

Guidance literature:

benzyl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate; With sodium hydride; In tetrahydrofuran; for 0.0833333h;

(2-trimethylethylsilylethoxy)methyl chloride; In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield:

2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride + benzyl chloroformate (501-53-1,94274-21-2) → benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (1190363-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.08 h / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.orglett.5b02921

Reference yield:

benzyl 4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (1190363-63-3) → tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(4-(2-((2-(trimethylsilyl)ethoxy)methoxy)-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamido)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate (1409943-98-1)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium on activated charcoal; hydrogen / methanol / 17 h / Inert atmosphere

2: triethylamine / dichloromethane / -20 °C / Inert atmosphere

3: triethylamine / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

With palladium on activated charcoal; hydrogen; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/acs.orglett.5b02921

upstream raw materials:

benzyl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

(2-trimethylethylsilylethoxy)methyl chloride

benzyl chloroformate

Downstream raw materials:

tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(4-(2-((2-(trimethylsilyl)ethoxy)methoxy)-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamido)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate