Patent ID: 6096898
Filing Date: 2000-08-01
Classification: C07D

Abstract:
A one pot process for preparing a compound of the formula formula (1) ##STR29## wherein Ar is substituted phenyl or pyridyl;R.sup.1 is methyl;HET is a group selected from ##STR30## R.sup.2 is selected from H, halo, lower alkyl, (C.sub.7 -C.sub.21) straight chain alkyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, alkoxyalkyl, alkoxyalkoxy, lower alkenyl, haloalkenyl, CN, NO.sub.2, CO.sub.2 R.sup.6, CON(R.sup.6).sub.2, (C.sub.3 -C.sub.6) cycloalkyl, S(O).sub.m R.sup.6, SCN, pyridyl, substituted pyridyl, isoxazolyl, substituted isoxazolyl, naphthyl, substituted naphthyl, phenyl, substituted phenyl, --(CH.sub.2).sub.n R.sup.6, --CH.dbd.CHR.sup.6, --C.tbd.-CR.sup.6, --CH.sub.2 OR.sup.6, --CH.sub.2 SR.sup.6, --CH.sub.2 NR.sup.6 R.sup.6, --OCH.sub.2 R.sup.6, --SCH.sub.2 R.sup.6, --NR.sup.6 CH.sub.2 R.sup.6, ##STR31## R.sup.3 and R.sup.4 are independently H, halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, CN, CO.sub.2 R.sup.6, CON(R.sup.6).sub.2, or S(O).sub.m alkyl, orif R.sup.3 and R.sup.4 are attached to adjacent carbon atoms, they may join to form a 5 or 6 member saturated or unsaturated carbocyclic ring which may be substituted by 1 or 2 halo, lower alkyl, lower alkoxy or haloalkyl groups;if R.sup.2 and R.sup.3 are attached to adjacent carbon atoms, they may combine to form a 5 or 6 member saturated or unsaturated carbocyclic ring which may be substituted by 1 or 2 halo, lower alkyl, lower alkoxy or haloalkyl groups;R.sup.5 is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;R.sup.6 is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;m is 0, 1, or 2; andn is 1 or 2;p is an integer from 2 to 6;which comprises the steps of:(a) reacting a compound of formula (2) ##STR32## wherein Ar is as defined in formula (1) and R.sup.7 is lower alkyl, or an acid addition salt thereof, with an acid chloride of the formula (3) ##STR33## wherein HET is as defined in formula (1), in 1,2-dichloroethane in the presence of an organic or inorganic .sub.-- base to produce the adduct-intermediate of formula (4) ##STR34## wherein Ar, R.sup.7, and HET are as defined above, and (b) without isolating said adduct-intermediate, adding methyl hydrazine to the reaction mixture to produce the compound of formula (1), and(c) adding octane to the reaction mixture to crystallize the product of formula (1).