2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole

Base Information

• Chemical Name: 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole
• CAS No.: 247133-80-8
• Molecular Formula: C₄₂H₄₈N₆O₇
• Molecular Weight: 748.879

Synonyms:

Chemical Property of 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole

There total 14 articles about 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole 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:

4-chloro-3-nitrobenzonitrile (939-80-0) → 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole (247133-80-8)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N / ethanol / 18 h / 20 - 50 °C

2: H₂ / Pd/C / tetrahydrofuran / 2 h / 20 °C / 760 Torr

3: 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / CHCl₃ / 3 h / 20 °C

4: AcOH / 96 h / 90 °C

5: aq. Na₂CO₃ / tetrahydrofuran / 12 h / 20 °C

6: EDC; HOBt / dimethylformamide / 15 h / 20 °C

7: H₂ / Pd/C / tetrahydrofuran / 7 h / 20 °C / 2280 Torr

8: Et₃N / CHCl₃ / 18 h / 20 °C

With hydrogen; sodium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.06.009

Reference yield:

tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate (138227-63-1) → 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole (247133-80-8)

Guidance literature:

Multi-step reaction with 9 steps

1: aq. NaHCO₃ / tetrahydrofuran / 1 h / 20 °C

2: NaH / dimethylformamide / 2 h / 20 °C

3: NaOH / tetrahydrofuran; ethanol / 1 h / 50 °C

4: 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / CHCl₃ / 3 h / 20 °C

5: AcOH / 96 h / 90 °C

6: aq. Na₂CO₃ / tetrahydrofuran / 12 h / 20 °C

7: EDC; HOBt / dimethylformamide / 15 h / 20 °C

8: H₂ / Pd/C / tetrahydrofuran / 7 h / 20 °C / 2280 Torr

9: Et₃N / CHCl₃ / 18 h / 20 °C

With sodium hydroxide; hydrogen; sodium hydride; sodium hydrogencarbonate; sodium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.06.009

Reference yield:

tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate (138227-62-0) → 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole (247133-80-8)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / Pd/C / ethanol; tetrahydrofuran / 3 h / 20 °C / 2280 Torr

2: aq. NaHCO₃ / tetrahydrofuran / 1 h / 20 °C

3: NaH / dimethylformamide / 2 h / 20 °C

4: NaOH / tetrahydrofuran; ethanol / 1 h / 50 °C

5: 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / CHCl₃ / 3 h / 20 °C

6: AcOH / 96 h / 90 °C

7: aq. Na₂CO₃ / tetrahydrofuran / 12 h / 20 °C

8: EDC; HOBt / dimethylformamide / 15 h / 20 °C

9: H₂ / Pd/C / tetrahydrofuran / 7 h / 20 °C / 2280 Torr

10: Et₃N / CHCl₃ / 18 h / 20 °C

With sodium hydroxide; hydrogen; sodium hydride; sodium hydrogencarbonate; sodium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.06.009

upstream raw materials:

4-Methoxycarbonylbenzoyl chloride

2-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenylaminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimdazole

4-chloro-3-nitrobenzonitrile

tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Downstream raw materials:

N-(5-carbamimidoyl-1-cyclohexylcarbamoylmethyl-1H-benzoimidazol-2-ylmethyl)-N-[4-(piperidin-4-yloxy)-phenyl]-terephthalamic acid methyl ester

2-[N-[4-(1-tert-butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonylbenzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-benzimidazole-5-carboxamidine

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