4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile

Base Information

• Chemical Name: 4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile
• CAS No.: 847614-93-1
• Molecular Formula: C₂₇H₂₅ClFN₅
• Molecular Weight: 473.98
• Mol file: 847614-93-1.mol

Synonyms:4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile

Chemical Property of 4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile

There total 5 articles about 4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile 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: 100.0%

4-[[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-(3'-cyano-biphenyl-4-yl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (847614-90-8) → 4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile (847614-93-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2006.04.061

Reference yield:

6-chloro-2-chloromethyl-5-fluoro-1H-benzimidazole → 4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile (847614-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / K₂CO₃ / acetonitrile / 20 °C

2: 100 percent / TFA / CH₂Cl₂

With potassium carbonate; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2006.04.061

Reference yield:

4-(4-bromobenzoyl)piperidine-1-carboxylic acid tert-butyl ester (439811-37-7) → 4'-{[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-piperidin-4-yl-methyl}-biphenyl-3-carbonitrile (847614-93-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NH₄OAc; NaCNBH₃ / methanol / 20 °C

2: 57 percent / Pd(PPh₃)4; aq. Na₂CO₃ / toluene; methanol / Heating

3: 60 percent / K₂CO₃ / acetonitrile / 20 °C

4: 100 percent / TFA / CH₂Cl₂

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium acetate; sodium cyanoborohydride; sodium carbonate; potassium carbonate; trifluoroacetic acid; In methanol; dichloromethane; toluene; acetonitrile; 2: Suzuki reaction;

DOI:10.1016/j.bmcl.2006.04.061

upstream raw materials:

4-[[(6-chloro-5-fluoro-1H-benzoimidazol-2-ylmethyl)-amino]-(3'-cyano-biphenyl-4-yl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

4-(4-bromobenzoyl)piperidine-1-carboxylic acid tert-butyl ester

4-[amino-(4-bromo-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

4-[amino-(3'-cyano-biphenyl-4-yl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester