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

Base Information

• Chemical Name: N-(5-carbamimidoyl-1-cyclohexylcarbamoylmethyl-1H-benzoimidazol-2-ylmethyl)-N-[4-(piperidin-4-yloxy)-phenyl]-terephthalamic acid methyl ester
• CAS No.: 751467-34-2
• Molecular Formula: C₃₇H₄₃N₇O₅
• Molecular Weight: 665.792
• Mol file: 751467-34-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about N-(5-carbamimidoyl-1-cyclohexylcarbamoylmethyl-1H-benzoimidazol-2-ylmethyl)-N-[4-(piperidin-4-yloxy)-phenyl]-terephthalamic acid methyl ester 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:

2-[N-[4-(1-tert-butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonylbenzoyl)aminomethyl]-1-(cyclohexylcarbamoylmethyl)-benzimidazole-5-carboxamidine (247133-81-9) → N-(5-carbamimidoyl-1-cyclohexylcarbamoylmethyl-1H-benzoimidazol-2-ylmethyl)-N-[4-(piperidin-4-yloxy)-phenyl]-terephthalamic acid methyl ester (751467-34-2)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.bmcl.2004.06.009

Reference yield:

4-chloro-3-nitrobenzonitrile (939-80-0) → N-(5-carbamimidoyl-1-cyclohexylcarbamoylmethyl-1H-benzoimidazol-2-ylmethyl)-N-[4-(piperidin-4-yloxy)-phenyl]-terephthalamic acid methyl ester (751467-34-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Et₃N / ethanol / 18 h / 20 - 50 °C

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

3.1: 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / CHCl₃ / 3 h / 20 °C

4.1: AcOH / 96 h / 90 °C

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

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

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

8.1: Et₃N / CHCl₃ / 18 h / 20 °C

9.1: H₂S; pyridine; Et₃N / 12 h / 20 °C

10.1: MeI / acetone; methanol / 1 h / Heating

10.2: NH₄OAc / ethanol / 3 h / 75 °C

11.1: TFA / CHCl₃ / 0.08 h / 20 °C

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

DOI:10.1016/j.bmcl.2004.06.009

Reference yield:

tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate (138227-63-1) → N-(5-carbamimidoyl-1-cyclohexylcarbamoylmethyl-1H-benzoimidazol-2-ylmethyl)-N-[4-(piperidin-4-yloxy)-phenyl]-terephthalamic acid methyl ester (751467-34-2)

Guidance literature:

Multi-step reaction with 12 steps

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

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

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

4.1: 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / CHCl₃ / 3 h / 20 °C

5.1: AcOH / 96 h / 90 °C

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

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

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

9.1: Et₃N / CHCl₃ / 18 h / 20 °C

10.1: H₂S; pyridine; Et₃N / 12 h / 20 °C

11.1: MeI / acetone; methanol / 1 h / Heating

11.2: NH₄OAc / ethanol / 3 h / 75 °C

12.1: TFA / CHCl₃ / 0.08 h / 20 °C

With pyridine; sodium hydroxide; hydrogen sulfide; 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; trifluoroacetic acid; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmcl.2004.06.009

upstream raw materials:

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

4-chloro-3-nitrobenzonitrile

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

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