Method of preparing a 5h-dibenz[b,f]azepine-5-carboxamide

Details Method of preparing a 5h-dibenz[b,f]azepine-5-carboxamide Method of preparing a 5h-dibenz[b,f]azepine-5-carboxamide

C - Chemistry, Metallurgy

07

D

C07D 223/18 (2006.01) C07D 223/26 (2006.01) C07D 223/28 (2006.01)

Patent

CA 2486560

The present invention provides a method of preparing a 5H-dibenz[b,f]azepine-5- carboxamide of formula (1) wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen, nitro, cyano, carboxyl, A, -CO(A), -OCO(A), -O(A), -N(A)2, -CON(A)2, and -COO(A), wherein A is selected from the group consisting of C-1-C10 alkyl, C3-C10 cycloalkyl, C-2- C10 alkenyl, C-5-C10 cycloalkenyl, C-2-C10 alkynyl, and C-6-C20 aryl, wherein the two A groups of -N(A)2 and -CON(A)2 can be the same or different, and wherein R2 and R3 can together form a bond; comprising reacting a 5H- dibenz[b,f]azepine of formula (2) with a) a cyanate salt selected from the group consisting of alkali metal cyanate salts and alkaline-earth metal cyanate salts, and b) a salt of an amino compound having no N-H bonds, wherein the salt has a Ka (25~ C) of at least about 10 x 10-11.

L'invention concerne un procédé d'élaboration de 5H-dibenz[b,f]azépine-5-carboxamide de formule (1). Dans cette formule, R?1¿, R?2¿, R?3¿, et R?4¿ sont choisis indépendamment dans le groupe comprenant hydrogène, halogène, nitro, cyano, carboxyle, A, -CO(A), -OCO(A), -O(A), -N(A)¿2?, -CON(A)¿2?, et -COO(A), A étant lui-même choisi dans le groupe qui comprend alkyle C¿1?-C¿10?, cycloalkyle C¿3?-C¿10?, alcényle C¿2?-C¿10?, cycloalcényle C¿5?-C¿10?, alkynyle C¿2?-C¿10?, et aryle C¿6?-C¿20?. Les deux groupes A de -N(A)¿2? et -CON(A)¿2? peuvent être identiques ou différents, et R?2¿ et R?3¿ peuvent former ensemble une liaison. Le procédé consiste à faire réagir de la 5H-dibenz[b,f]azépine de formule (2) avec a) un sel de cyanate appartenant au groupe constitué de sels de cyanate de métal alcalin, et b) un sel de composé amino sans liaisons N-H, le sel ayant un K¿a? (25· C) d'au moins environ 10 x 10?-11¿.

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