N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride

Base Information

• Chemical Name: N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride
• CAS No.: 1612893-66-9
• Molecular Formula: C₁₉H₁₉N₅O₂*ClH
• Molecular Weight: 385.853
• Mol file: 1612893-66-9.mol

Synonyms:N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride

Chemical Property of N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride

There total 7 articles about N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride 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: 86.0%

5-(4-guanidinophenyl)isoxazole-3-carboxylic acid hydrochloride (1612893-55-6) + 2,6-dimethylaniline (87-62-7) → N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride (1612893-66-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dimethyl sulfoxide; at 20 ℃; for 48h;

DOI:10.1016/j.bmcl.2014.04.118

Reference yield:

4-(4-nitrophenyl)-2,4-dione-butyric acid ethyl ester (54808-56-9) → N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride (1612893-66-9)

Guidance literature:

Multi-step reaction with 5 steps

1: hydroxylamine hydrochloride / ethanol / 4 h / Reflux

2: tin(II) chloride dihdyrate / ethyl acetate / 6 h / Reflux

3: hydrogenchloride / ethanol; water / 8 h / Reflux

4: sodium hydroxide / water; methanol / 3 h / Reflux

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dimethyl sulfoxide / 48 h / 20 °C

With hydrogenchloride; tin(II) chloride dihdyrate; hydroxylamine hydrochloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In methanol; ethanol; water; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/j.bmcl.2014.04.118

Reference yield:

ethyl 5-(4-nitrophenyl)isoxazole-3-carboxylate (159670-70-9) → N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride (1612893-66-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tin(II) chloride dihdyrate / ethyl acetate / 6 h / Reflux

2: hydrogenchloride / ethanol; water / 8 h / Reflux

3: sodium hydroxide / water; methanol / 3 h / Reflux

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dimethyl sulfoxide / 48 h / 20 °C

With hydrogenchloride; tin(II) chloride dihdyrate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In methanol; ethanol; water; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/j.bmcl.2014.04.118

upstream raw materials:

5-(4-guanidinophenyl)isoxazole-3-carboxylic acid hydrochloride

2,6-dimethylaniline

4-(4-nitrophenyl)-2,4-dione-butyric acid ethyl ester

ethyl 5-(4-nitrophenyl)isoxazole-3-carboxylate

Refernces

• 1、 Zhao, Juntao,Tian, Wei,Qi, Jingjing,Lv, Diya,Liu, Yang,Jiang, Yan,Dong, Guoqiang,Chen, Qianqian,Zhou, Youjun,Zhu, Ju,Wang, Heling,Sheng, Chunquan,Lv, Jiaguo. "Design and synthesis of phenylisoxazole derivatives as novel human acrosin inhibitors". supporting information. p. 2802 - 2806. Retrieved 2014/06/10.