A New and Practical Synthesis of Cariprazine through the Facile Construction of 2-[trans-4-(3,3-Dimethylureido)cyclohexyl]acetic Acid

Xiaowen Chen; Feng Ni; Yu Liu; Lei Fu; Jianqi Li

doi:10.1055/s-0035-1561865

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(18): 3120-3126
DOI: 10.1055/s-0035-1561865

paper

A New and Practical Synthesis of Cariprazine through the Facile Construction of 2-[trans-4-(3,3-Dimethylureido)cyclohexyl]acetic Acid

Autor*innen

Xiaowen Chen

^aSchool of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Rd, Shanghai 200240, P. R. of China eMail: leifu@sjtu.edu.cn

^bNovel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry,285 Gebaini Rd, Shanghai 201203, P. R. of China eMail: li.jianqi@sipi.com.cn
Feng Ni

^bNovel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry,285 Gebaini Rd, Shanghai 201203, P. R. of China eMail: li.jianqi@sipi.com.cn
Yu Liu

^bNovel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry,285 Gebaini Rd, Shanghai 201203, P. R. of China eMail: li.jianqi@sipi.com.cn
Lei Fu*

^aSchool of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Rd, Shanghai 200240, P. R. of China eMail: leifu@sjtu.edu.cn
Jianqi Li*

^bNovel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry,285 Gebaini Rd, Shanghai 201203, P. R. of China eMail: li.jianqi@sipi.com.cn

Abstract

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Abstract

A new, practical, and improved synthetic route to cariprazine is described. The key step is the facile preparation of 2-[4-(3,3-dimethylureido)cyclohexyl]acetic acid in the trans configuration through direct recrystallization. The entire synthetic procedure was accomplished under mild conditions while avoiding tedious purification processes. The trans configuration of cariprazine was confirmed by X-ray crystallographic analysis.

Key words

cariprazine - antipsychotic agents - synthetic methods - recrystallization - trans configuration - X-ray crystallography

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Referenzen

References
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13 CCDC 1414994 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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