Abstract
A nonracemic synthesis of the glucokinase-glucokinase regulatory protein disruptor AMG-3969 (5) is reported. Key features of the synthetic approach are an asymmetric synthesis of the 2-alkynyl piperazine core via a base-promoted isomerization and a revised approach to the synthesis of the aminopyridinesulfonamide with an improved safety profile.
MeSH terms
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Benzyl Compounds / chemical synthesis*
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Benzyl Compounds / chemistry
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Carbamates / chemical synthesis*
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Carbamates / chemistry
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Carrier Proteins / antagonists & inhibitors*
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Carrier Proteins / chemistry
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Indicators and Reagents / chemistry
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Isomerism
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Molecular Structure
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Piperazines / chemical synthesis*
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Piperazines / chemistry
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Pyridines / chemical synthesis*
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Pyridines / chemistry
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Sulfonamides / chemical synthesis*
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Sulfonamides / chemistry
Substances
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1-benzyl-3-(1-propyn-1-yl)piperazine
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1-benzyl-3-(2-propyn-1-yl)-2,5-piperazinedione
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2-(4-(4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol
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Benzyl Compounds
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Carbamates
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Carrier Proteins
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Indicators and Reagents
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Piperazines
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Pyridines
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Sulfonamides
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glucokinase regulatory protein
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tert-butyl(5-(chlorosulfonyl)-2-pyridinyl)carbamate