Process for preparation of 1,2,3-triazole-4 carboxamides
AssigneeTaro Pharmaceutical Industries Ltd.
InventorsShimon Cherynyak, Rosa Cyjon, Ilana Ozer
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Abstract
The invention relates to the preparation of 1,2,3-triazole-4-carboxamide of general Formula I: wherein R1 and R2 may be the same or different and are selected from H, F, Cl, Br, I, OR, C(O)R, NH2, NHR or NR2. R can be a linear or branched alkyl group, for example a C1-C4 alkyl group. In exemplary embodiments, R1 and R2 are independently selected from H, F, Cl, Br, and I. The compound of Formula I can be Rufinamide.
Claims22
A process for the preparation of a 1,2,3-triazole-4-carboxamide of formula I
- comprising:
- (a) reacting a benzyl chloride of general formula III with an azide to obtain a benzylazide of general formula IV, wherein R1 and R2 are as defined above;
- (b) reacting the benzylazide of general Formula IV with a 2-halideacrylamide of general Formula V, wherein X is selected from Cl, Br and I, to obtain the 1,2,3-triazole-4-carboxamide of general Formula I;
- and
- (c) isolating the obtained 1,2,3-triazole-4-carboxamide of general Formula I
- wherein R1 and R2 are independently selected from the group consisting of H, F, Cl, Br, I, OR, C(O)R, NH2, NHR or NR2, wherein R is a linear or branched alkyl group.
A process for the preparation of rufinamide of Formula II,
- comprising:
- (a) reacting 2,6-difluorobenzyl chloride with sodium azide to obtain 2,6-difluorobenzylazide;
- (b) reacting 2,6-difluorobenzylazide with 2-chloroacrylamide to form rufinamide;
- and
- isolating the obtained rufinamide.
A process for the preparation of a 1,2,3-triazole-4-carboxamide of formula I
- wherein R1 and R2 are independently selected from H, F, Cl, Br and I, comprising:
- reacting a benzylazide of general Formula IV wherein R1 and R2 are independently selected from H, F, Cl, Br and I, with a 2-halideacrylamide of general Formula V wherein X is selected from Cl, Br and I, to obtain the 1,2,3-triazole-4-carboxamide of general Formula I;
- and
- isolating the obtained 1,2,3-triazole-4-carboxamide of general Formula I;
- wherein R1 and R2 are independently selected from the group consisting of H, F, Cl, Br, I, OR, C(O)R, NH2, NHR or NR2, wherein R is a linear or branched alkyl group.
Dependencies are inferred from the claim text.