Process for the synthesis of substituted 1-benzyl-3-(1-(isoxazol-4-ylmethyl)-1H-pyrazol-4-yl)imidazolidine-2,4-diones
The present invention relates to processes and intermediates for the preparation of compounds of formula (I): or a salt or oxide thereof wherein Alk, M 1 , M 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and n are as described herein. The present invention also relates to compounds of formula (I) and composition comprising a compound of formula (I). Also disclosed is a method of altering or improving the taste of a composition that includes adding to the composition at least one compound of formula (I), in an amount effective to obtain a modified composition having altered or improved taste relative to an otherwise identical composition lacking said compound.
1. A compound of formula (II):
wherein Alk is an alkyl group;
M 1 is N or CR 8 , wherein R 8 is H or substituted or unsubstituted alkyl;
M 2 is N or CR 9 , wherein R 9 is H or substituted or unsubstituted alkyl;
R 1 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted alkoxy, and substituted or unsubstituted alkylaryl;
R 2 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted alkoxy, and substituted or unsubstituted alkylaryl; and
LG is selected from the group consisting of imidazolyl, O-alkyl, O-aryl, O-heteroaryl, O-alkyaryl, O-halogenated alkyl, and halo,
or an oxide thereof, a salt thereof, or a solvate thereof.
2. A compound according to claim 1 , wherein the compound of formula (II) is represented by formula (IIa):
wherein LG, R 1 , and R 2 are the same as defined in claim 1 .
3. A compound according to claim 1 which is selected from the group consisting of
wherein
LG is selected from the group consisting of O-alkyl, O-aryl, O-heteroalkyl O-heteroaryl, O-alkyaryl, O-halogenated alkyl, and halo,
or an oxide, salt, or solvate thereof.
4. A composition comprising a compound synthesized according to claim 1 .
5. The composition of claim 4 , wherein the compound is a compound of formula (IIa) or a salt, solvate, or an obvious chemical equivalent thereof.
6. An oxide, a salt, or a solvate of a compound according to claim 1 suitable for animal or human consumption.
7. The composition of claim 4 , wherein the compound is selected from the group consisting of
or a salt, solvate, or an obvious chemical equivalent thereof.