| US 7,339,058 B2 | ||
| Process for the preparation of N-([1,2,4]triazolopyrimidin-2-yl)aryl sulfonamides | ||
| Christopher Thomas Hamilton, Midland, Mich. (US) | ||
| Assigned to Dow AgroSciences LLC, Indianapolis, Ind. (US) | ||
| Filed on Mar. 24, 2005, as Appl. No. 11/88,448. | ||
| Claims priority of provisional application 60/557022, filed on Mar. 26, 2004. | ||
| Prior Publication US 2005/0215570 A1, Sep. 29, 2005 | ||
| Int. Cl. C07D 487/04 (2006.01); A61K 31/519 (2006.01) | ||
| U.S. Cl. 544—263 [544/254] | 3 Claims |
1. An improved process for the preparation of an N-([1,2,4]triazolopyrimidin-2-yl)aryl sulfonamide of formula I:
 X represents CH or N;
Y represents CZ or N with the proviso that only one of X or Y is N;
W represents H or OR with the proviso that when Y represents CZ, then W represents H;
Z represents OR;
R represent CH3 or CH2CH3;
Ar represents
 A and B independently represent H, halo, CF3, R or OR1;
D represents H, halo or R;
E and G represent S or CB with the proviso that one of E or G is S; and
R1 represents C1-C4 alkyl, C3-C4 alkenyl, or C3-C4 alkynyl each optionally possessing up to two chloro, bromo or C1-C4 alkyl substituents or up to the maximum possible number of fluoro substituents
which comprises combining a sulfonyl chloride compound of the formula:
ArSO2Cl
wherein
Ar is defined as above with an amine compound of the formula:
 R, X, Y and W are defined as above in the presence of an aromatic tertiary amine base and a catalytic amount of an N-aryl-sulfilimine compound of the formula:
 R, X, Y and W are defined as above;
R2 represents CH3, or CH2CH3; and
R3 represents R2 or R2 and R3 together represent tetramethylene or their salts,
wherein the improvement comprises using 3-picoline or 3,5-lutidine as the aromatic tertiary amine base.
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