Preparation of thieno-imidazole derivatives

Details Preparation of thieno-imidazole derivatives Preparation of thieno-imidazole derivatives

C - Chemistry, Metallurgy

07

D

260/298.3

C07D 495/04 (2006.01)

Patent

CA 1270254

64680-369 ABSTRACT OF THE DISCLOSURE Disclosed are a process for the preparation of a thio- substituted intermediate (VA) by reacting a substituted imidazo- thiazole alcohol (VIIA) with anhydrous hydrogen fluoride and a process for the preparation of a thieno-imidazole derivative (IV), particularly descarboxybiotin (R = (CH2)4CH3), a useful intermediate for the preparation of d-biotin, by reacting the thio-substituted intermediate (in which X is 0) for example descarboxythiobiotin, with an epoxy compound (VI) in an alkanol solvent; Image (VA) (VIIA) Image (VI) (IV) 64680-359 twhere R is -(CH2)4CH3, -(CH2)3OR1 or -(CH2)50R1, R1 is (C1-C6)alkyl, -(CH2)4CN or -(CH2)4COOR2, R2 is (C1-C6)alkyl or phenyl, R4 and R5 when taken together form a C5-C6 cycloalkyl group or -(CH2)2-Y-(CH2)2-, Y is S, O or NCOOR6 (where R6 is (C1-C6)alkyl) or R4 and R5 are each (C1-C6)alkyl, (C5-C6)cycloalkyl or phenyl, and R3 is H, CH3 or CH2OH].

503855

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