Practical and efficient synthesis of the (R)-atropisomer of a 4-phenyl 1,2,4-triazole derivative as a selective GlyT1 inhibitor

被引:8
|
作者
Sugane, Takashi [1 ]
Hamada, Noritaka [1 ]
Tobe, Takahiko [1 ]
Hamaguchi, Wataru [1 ]
Shimada, Itsuro [1 ]
Maeno, Kyoichi [1 ]
Miyata, Junji [1 ]
Suzuki, Takeshi [1 ]
Kimizuka, Tetsuya [1 ]
Sakamoto, Shuichi [1 ]
Tsukamoto, Shin-ichi [1 ]
机构
[1] Astellas Pharma Inc, Drug Discovery Res, Tsukuba, Ibaraki 3058585, Japan
关键词
POWDER DIFFRACTION; BIOLOGICAL EVALUATION; SCHIZOPHRENIA; REFINEMENT; TRANSPORT; CRYSTAL; ACID; NMR;
D O I
10.1016/j.tetasy.2012.10.005
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Herein we describe a novel and efficient method for synthesizing the (R)-atropisomer of 3-[3-ethyl-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methylbenzonitrile 1, a novel GlyT1 inhibitor. The diastereomeric salt formation of 3-[3-ethyl-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methylbenzoic acid 7 with (1R,2S)-(-)-2-amino-1,2-diphenylethanol afforded the desired (R)-atropisomer. We also report the determination of the absolute configuration of (R)-7 by powder X-ray diffraction. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1528 / 1533
页数:6
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