2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid

Base Information

• Chemical Name: 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid
• CAS No.: 853069-75-7
• Molecular Formula: C₂₉H₃₁ClFN₅O₅
• Molecular Weight: 584.047
• Mol file: 853069-75-7.mol

Synonyms:2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid

Chemical Property of 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid

There total 12 articles about 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid 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%

methyl 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylate (853069-35-9) → 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid (853069-75-7)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 6h;

DOI:10.1016/j.bmc.2014.12.051

Reference yield:

methyl 4-({[2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-4-iodo-1H-imidazol-5-yl]carbonyl}amino)benzoate (853070-09-4) → 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid (853069-75-7)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

2: silver (I) hydrogen carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 1 h / 150 °C

3: 10% Pd/C; ammonium formate / methanol / 2 h / Reflux

4: potassium carbonate / N,N-dimethyl-formamide / 3 h / 65 °C

5: water; sodium hydroxide / tetrahydrofuran; methanol / 6 h / 20 °C

With silver (I) hydrogen carbonate; 10% Pd/C; water; palladium diacetate; ammonium formate; potassium carbonate; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2012.07.046

Reference yield:

methyl 4-[{[2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-4-iodo-1H-imidazol-5-yl]carbonyl}(methyl)amino]benzoate (853069-87-1) → 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chloro-5-fluorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylic acid (853069-75-7)

Guidance literature:

Multi-step reaction with 4 steps

1: silver (I) hydrogen carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 1 h / 150 °C

2: 10% Pd/C; ammonium formate / methanol / 2 h / Reflux

3: potassium carbonate / N,N-dimethyl-formamide / 3 h / 65 °C

4: water; sodium hydroxide / tetrahydrofuran; methanol / 6 h / 20 °C

With silver (I) hydrogen carbonate; 10% Pd/C; water; palladium diacetate; ammonium formate; potassium carbonate; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2012.07.046

upstream raw materials:

methyl 4-({[2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-4-iodo-1H-imidazol-5-yl]carbonyl}amino)benzoate

methyl 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylate

methyl 4-[{[2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-4-iodo-1H-imidazol-5-yl]carbonyl}(methyl)amino]benzoate

methyl 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-(2-chlorobenzyl)-5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinoline-8-carboxylate