Preparation of 4-(4-flourophenyl)-6-alkyl-2-N-alkansulfonyl-N-alkylamino)pyrimidine-5-carboxylic acid ester.
AssigneeLonza Ltd.
InventorUlrich Veith
Life of this patent
Estimating the term…
Abstract
A process for the preparation of a 4-(4-flourophenyl)-6-alkyl-2-N-alkansulfonyl-N-alkylamino)pyrimidine-5-carboxylic acid ester of formula (Ib), in which R1, R2, R3 and R4 are identical or different and are each a C1-6-alkyl. A 2-[-1-amino-1-(4-flourophenyl)methylene]-4-alkyl-3-oxo-alkanoic acid ester of formula (IIIb), in which R3 and R4 have the above-mentioned meanings, is reacted with an N-cyano-N-alkylalkanesulfonamide, optionally isolated or prepares in situ, of formula (IVb), in which R1 and R2 have the above-mentioned meanings, to give the final product of formula (Ib).
Claims23
Process for the preparation of compounds of the general formula
- 15
- in which
- R is hydrogen or a group of the formula —SO2R1;
- R1 is C1-6-alkyl;
- R2 is hydrogen or C1-6-alkyl;
- R3 is C1-6-alkyl;
- R4 is C1-6-alkyl,
- characterized in that, in a first stage, a compound of the general formula
- 16
- in which R3 and R4 have the abovementioned meaning, is reacted in the presence of a Lewis acid with 4-fluorobenzonitrile to give a compound of the general formula
- 17
- in which R3 and R4 have the abovementioned meaning, and in a second stage the compound of the formula III obtained is reacted with a compound of the general formula
- 18
- in which R and R2 have the abovementioned meaning, to give the final product of the formula I.
Methyl 2-[1-amino-1-(4-fluorophenyl)-methylene]-4-methyl-3-oxopentanoate.
Process for the preparation of 4-(4-fluorophenyl)-6-alkyl-2-N-alkansulphonyl-N-alkylamino)-pyrimidine-5-carboxylic acid esters of the general formula
- 24
- in which R1, R2, R3 and R4 are identical or different and are a C1-6-alkyl group, characterized in that a 2-[-1-amino-1-(4-fluorophenyl)methylene]-4-alkyl-3-oxo-alkanoic acid ester of the general formula
- 25
- in which R3 and R4 are a C1-6-alkyl group, is reacted with an N-cyano-N-alkylalkanesulphonamide, optionally isolated or prepared in situ, of the general formula
- 26
- in which R1 and R2 are a C1-6-alkyl group, to give the final product of the formula Ib.
Process for the preparation of N-cyano-N-alkylalkanesulphonamides of the general formula
- 27
- in which R1 and R2 are a C1-6-alkylgroup characterized in that a cyanogen halide is prepared using an N-alkyl-alkanesulphonamide of the general formula
- 28
- in which R1 and R2 are a C1-6-alkyl group, in the presence of a base.
N-Cyano-N-alkylalkanesulphonamides of the general formula
- 29
- in which R1 and R2 are a C1-6-alkyl group.
N-Cyano-N-methylmethanesulphonamide.
Dependencies are inferred from the claim text.