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18 F‐labelling of a potent nonpeptide CCR1 antagonist: synthesis of 1‐(5‐chloro‐2‐{2‐[(2R)‐4‐(4‐[ 18 F]fluorobenzyl)‐2‐methylpiperazin‐1‐yl]‐2‐oxoethoxy}phenyl)urea in an automated module
Author(s) -
Mäding P.,
Füchtner F.,
Johannsen B.,
Steinbach J.,
Hilger C. S.,
Friebe M.,
HalksMiller M.,
Horuk R.,
Mohan R.
Publication year - 2006
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1023
Subject(s) - chemistry , piperazine , sodium cyanoborohydride , reductive amination , solid phase extraction , urea , derivative (finance) , radiochemistry , nuclear chemistry , labelling , chromatography , extraction (chemistry) , medicinal chemistry , organic chemistry , biochemistry , financial economics , economics , catalysis
The synthesis of 1‐(5‐chloro‐2‐{2‐[(2R)‐4‐(4‐[ 18 F]fluorobenzyl)‐2‐methylpiperazin‐1‐yl]‐2‐oxoethoxy}phenyl)urea ( [ 18 F]4 ), a potent nonpeptide CCR1 antagonist, is described as a module‐assisted two‐step one‐pot procedure. The final product was obtained utilizing the reductive amination of the formed 4‐[ 18 F]fluorobenzaldehyde ( 2 ) with a piperazine derivative 3 and sodium cyanoborohydride. After HPLC purification of the final product [ 18 F]4 , its solid phase extraction, formulation and sterile filtration, the isolated (not decay‐corrected) radiochemical yields of [ 18 F]4 were between 7 and 13% ( n =28). The time of the entire manufacturing process did not exceed 95 min. The radiochemical purity of [ 18 F]4 was higher than 95%, the chemical purity ⩾60% and the enantiomeric purity >99.5%. The specific radioactivity was in the range of 59–226 GBq/µmol at starting radioactivities of 23.6–65.0 GBq [ 18 F]fluoride. Copyright © 2006 John Wiley & Sons, Ltd.