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

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 22-23期

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

页码：1528 / 1533

页数：6

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