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Syntheses of stable-isotope labeled [M+7] and [M+6] 2-(methylamino)imidazole

✍ Scribed by Yinsheng Zhang

Publisher
John Wiley and Sons
Year
2002
Tongue
French
Weight
110 KB
Volume
45
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Stable isotope‐labeled 2‐methylaminoimidazole (M+7 and M+6) was required as an intermediate in the synthesis of mass labeled drug candidates. These two isotopomers were synthesized with total yields of 24 and 36%, respectively. Labeled 2‐aminoimidazole (M+4) was prepared from labeled isothiourea (M+3) and 2‐aminoacetaldehyde dimethyl acetal (M+1 and M+2). The (M+1) version of 2‐aminoacetaldehyde dimethyl acetal was obtained in two steps starting with potassium [^15^N]phthalimide, while the (M+2) version was prepared from the reduction of diethoxyacetamide with LiAlD~4~. Two different approaches for the preparation of 2‐methylaminoimidazole from aminoimidazole were explored. Attempts to prepare protected 2‐aminoimidazole to couple with CH~3~I (M+4) to form the desired labeled 2‐methyl‐aminoimidazole failed. However, methylation was achieved by applying N‐formamidation followed by deutero‐reduction. These successful syntheses allowed us to selectively label with nitrogen, carbon or hydrogen isotopes at most of the positions of 2‐methylaminoimidazole. Copyright © 2002 John Wiley & Sons, Ltd.

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