Patent ID: 7339057
Filing Date: 2008-03-04
Classification: C07D

Abstract:
1. A method for preparing a fused oxazinone of Formula 1, wherein K is, together with the two contiguous linking carbon atoms, a fused phenyl ring optionally substituted with from one to four substituents independently selected from G, U, W or R J is a pyrrole ring or a pyrazole ring, each optionally substituted with from one to four substituents independently selected from G, U, W or R each G is a 5- or 6-membered nonaromatic heterocyclie ring optionally with one or two ring members selected from the group consisting of C(═O), SO or S(O) each U is a phenyl ring, a benzyl group, a benzoyl group, a 5- or 6-membered heteroaromatic ring, an aromatic 8-, 9- or 10-membered fused carbobicyclic ring system, an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each optionally substituted with from one to four substituents independently selected from W; each W is independently C each R each R each E independently O, S, NR each M is independently O, NR Q is O or S; each R each R B(OR each R comprising: (1) contacting a carboxylic acid of Formula 2 with a sulfonyl chloride of Formula 4 wherein L is selected from alkyl, haloalkyl, and phenyl optionally substituted with from one to three substituents independently selected from alkyl or halogen; in the presence of a Formula 3 compound selected from the group consisting of pyridine, quinoline, isoquinoline and pyridine substituted with alkyl, dimethylamino, or pyrrolidino, the nominal mole ratio of sulfonyl chloride to carboxylic acid being from about 0.75 to 1.5; (2) contacting the mixture prepared in (1) with an ortho-amino aromatic carboxylic acid of Formula 5 in the presence of a Formula 3 compound selected from the group consisting of pyridine, quinoline, isoquinoline and pyridine substituted with alkyl, dimethylamino, or pyrrolidino, the nominal mole ratio of the ortho-amino aromatic carboxylic acid to carboxylic acid charged in (1) being from about 0.8 to 1.2; and (3) adding additional sulfonyl chloride to the mixture prepared in (2), the nominal mole ratio of additional sulfonyl chloride added in (3) to carboxylic acid charged in (1) being at least about 0.5.