methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl ester

Base Information

• Chemical Name: methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl ester
• CAS No.: 332426-50-3
• Molecular Formula: C₂₇H₂₄FN₅O₄S
• Molecular Weight: 533.583
• Mol file: 332426-50-3.mol

Synonyms:methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl ester

Chemical Property of methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl ester

There total 10 articles about methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl 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: 91.0%

2-fluoro-4-[(5-formyl-1H-imidazol-1-yl)methyl]benzonitrile (254108-49-1) + methanesulfonic acid 8-(2-oxopiperazin-1-yl)naphthalen-2-yl ester hydrochloride → methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl ester (332426-50-3)

Guidance literature:

With 4 A molecular sieve; sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 14h;

DOI:10.1021/ja003673q

Reference yield:

4-bromo-3-fluorotoluene (452-74-4) → methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl ester (332426-50-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / Pd(PPh₃)4 / dimethylformamide / 3 h / 80 °C

2.1: 43 percent / N-bromosuccinimide; 2,2'-azobisisobutyryonitrile / CCl₄ / 24 h / 100 °C

3.1: ethyl acetate / 20 h / 60 °C

3.2: methanol / 0.5 h / 60 °C

4.1: 83 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 2 h / 0 °C

5.1: 86 percent / SO₃*Py; triethylamine / dimethylsulfoxide / 0.75 h / 20 °C

6.1: 91 percent / sodium triacetoxyborohydride; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 14 h / 20 °C

With lithium hydroxide; N-Bromosuccinimide; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; sodium tris(acetoxy)borohydride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; water; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ja003673q

Reference yield:

1-(4-cyano-3-fluorobenzyl)-5-(acetoxymethyl)-imidazole hydrobromide → methanesulfonic acid 8-{4-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-ylmethyl]-2-oxopiperazin-1-yl}-naphthalen-2-yl ester (332426-50-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 2 h / 0 °C

2: 86 percent / SO₃*Py; triethylamine / dimethylsulfoxide / 0.75 h / 20 °C

3: 91 percent / sodium triacetoxyborohydride; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 14 h / 20 °C

With lithium hydroxide; pyridine-SO₃ complex; 4 A molecular sieve; sodium tris(acetoxy)borohydride; triethylamine; In tetrahydrofuran; water; dimethyl sulfoxide; 1,2-dichloro-ethane;

DOI:10.1021/ja003673q

upstream raw materials:

2-fluoro-4-[(5-formyl-1H-imidazol-1-yl)methyl]benzonitrile

8-amino-2-naphthol

4-bromo-3-fluorotoluene

2-chloro-N-(7-hydroxynaphthalen-1-yl)acetamide