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Synthesis of carbon-14 labeled 6-(4-fluorophenyl)-5-(4-pyridyl)-2,3-dihydroimidazo[2,1-b]thiazole (SK&F 86002)

✍ Scribed by S. G. Senderoff; J. R. Heys; D. W. Blackburn

Publisher
John Wiley and Sons
Year
1987
Tongue
French
Weight
331 KB
Volume
24
Category
Article
ISSN
0022-2135

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✦ Synopsis

S W 86002, 6-(4-f luorophenyl) -5-(4-pyridyl) -2,3-dihydroimidazo[2,l-b] thiazole, was synthesized labeled pith carbon-14 at C-1 or 14-2,3 using either [ C] thiourea or 1,2-dibromo [ C 3 ethane, respectively. The synthetic route, invogving the condensation of an asymmetric benzoin with thiourea followed by alkylation, gave a mixture of S W 86002 and structural isomer S W 86055, 5-(4f luorophenyl) -6-(4-pyridyl) -2,3-dihydroimidazo-[2,l-b] thiazole. The two products were separated easily brlflash chromatography. The use of 1,2dibromo[ C2]ethane as f.& labeling reagent was superior to the use of [ Clthiourea in this sequence, for the radiolabel was incorporated in the final step of 'the synthesis by an alkylation reaction, thus providing greatly increased overall radiochemical yields.

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