Processes and intermediates in the synthesis of...

C - Chemistry – Metallurgy – 07 – D

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C07D 239/10 (2006.01) C07C 69/734 (2006.01) C07C 235/34 (2006.01) C07C 255/37 (2006.01) C07C 259/06 (2006.01)

Patent

CA 2349119

Disclosed are processes for producing compounds of the formulae: Image (wherein X and Y are both -CN, -CONH2, -CO2alkyl or -CONHOH or together form a cyclic urea), by (1) reacting isovanillin with QCH2CO2H (in which Q is -CN, -CONH2, -CO2alkyl or -CONHOH) to yield (II) (in which X and Y are Q), (2) when required, converting (II) (in which X and Y are Q) to (II) (in which X and Y together form a cyclic urea) and (3) when required, reacting (II) with norborneol. The compounds (II) and (III) are useful as intermediates for producing 5- (3-[(2S or 2R) -exo- bicyclo[2.2.1.]hept-2-yloxy]-4-methoxyphenyl)-3,4,5,6- tetrahydropyrimidin-2(1H)-one that is useful as a pharmaceutical agent, e.g. antidepressant.

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