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

Base Information

• Chemical Name: benzyl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
• CAS No.: 1146637-16-2
• Molecular Formula: C₁₉H₂₀N₄O₃
• Molecular Weight: 352.393
• Mol file: 1146637-16-2.mol

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

Chemical Property of benzyl 4-(2-oxo-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:

SDS file from LookChem

Useful:

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

There total 6 articles about benzyl 4-(2-oxo-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: 69.0%

benzyl 4-[1-(2-chloro-pyridin-3-yl)-ureido]-piperidine-1-carboxylate (1146637-15-1) → benzyl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (1146637-16-2)

Guidance literature:

benzyl 4-[1-(2-chloro-pyridin-3-yl)-ureido]-piperidine-1-carboxylate; With sodium hydrogencarbonate; In tert-Amyl alcohol; Reflux;

palladium diacetate; 1,4-di(diphenylphosphino)-butane; In water; at 35 - 100 ℃;

Reference yield: 62.0%

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-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (1146637-16-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

Reference yield:

benzyl 4-oxo-1-piperidinecarboxylate (19099-93-5) → benzyl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (1146637-16-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trifluoroacetic acid; sodium tris(acetoxy)borohydride / isopropyl alcohol / 15 °C

1.2: 20 °C

2.1: tetrahydrofuran / -15 - 10 °C

3.1: sodium hydroxide / tetrahydrofuran / 50 °C

4.1: sodium hydrogencarbonate; 1,4-di(diphenylphosphino)-butane / palladium diacetate / tert-Amyl alcohol / 35 - 100 °C / Reflux

With sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; 1,4-di(diphenylphosphino)-butane; trifluoroacetic acid; sodium hydroxide; palladium diacetate; In tetrahydrofuran; tert-Amyl alcohol; isopropyl alcohol;

upstream raw materials:

benzyl chloroformate

benzyl 4-[1-(2-chloro-pyridin-3-yl)-ureido]-piperidine-1-carboxylate

2-chloro-3-aminopyridine

benzyl 4-oxo-1-piperidinecarboxylate

Downstream raw materials:

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

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