1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone

Base Information

• Chemical Name: 1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone
• CAS No.: 745074-50-4
• Molecular Formula: C₁₉H₂₄N₄O₂S₂
• Molecular Weight: 404.557
• Mol file: 745074-50-4.mol

Synonyms:1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone

Chemical Property of 1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone

There total 4 articles about 1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone 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: 88.0%

5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoic acid (745074-49-1) + N-acetylpiperidine (13889-98-0) → 1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone (745074-50-4)

Guidance literature:

With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 50 ℃; for 5h;

DOI:10.1016/j.bmcl.2006.01.115

Reference yield:

methyl 5-(chloromethyl)-2,3-dimethylbenzoate (745074-47-9) → 1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone (745074-50-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaBH₄ / ethanol / 2 h / 0 - 5 °C

1.2: 87 percent / ethanol / 16 h / 20 °C

2.1: 86 percent / aq. NaOH / methanol / Heating

3.1: 88 percent / BOP; 4-methylmorpholine / dimethylformamide / 5 h / 50 °C

With 4-methyl-morpholine; sodium hydroxide; sodium tetrahydroborate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.01.115

Reference yield:

5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoic acid methyl ester (745074-48-0) → 1-{4-[5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone (745074-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / aq. NaOH / methanol / Heating

2: 88 percent / BOP; 4-methylmorpholine / dimethylformamide / 5 h / 50 °C

With 4-methyl-morpholine; sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.01.115

upstream raw materials:

5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoic acid

N-acetylpiperidine

methyl 5-(chloromethyl)-2,3-dimethylbenzoate

5-(2-amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoic acid methyl ester

Downstream raw materials:

N-{5-[3-(4-acetyl-piperazine-1-carbonyl)-4,5-dimethyl-benzylsulfanyl]-thiazol-2-yl}-4-chloromethyl-benzamide