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

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-methyl...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2012-12, Vol.23 (22-23), p.1528-1533
Main Authors: Sugane, Takashi, Hamada, Noritaka, Tobe, Takahiko, Hamaguchi, Wataru, Shimada, Itsuro, Maeno, Kyoichi, Miyata, Junji, Suzuki, Takeshi, Kimizuka, Tetsuya, Sakamoto, Shuichi, Tsukamoto, Shin-ichi
Format: Article
Language:English
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Summary: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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2012.10.005