Patent ID: 7199240
Filing Date: 2007-04-03
Classification: C07D

Abstract:
1. A process for preparing a compound of Formula (I): which comprises: (A) reacting an aldehyde of Formula (II): with a cyclic amine compound of Formula (III): in an organic solveni and in the presence of a C 1-6 alkylcarboxylic acid and with removal of by-product water, to form a reaction mixture comprising an iminium salt of Formula (IV): (B) adding a tetrahydroborate salt to the reaction mixture of Step A to obtain a product comprising a compound of Formula (I) and one or more borane complexes thereof; and (C) treating the product of Step B with a catalyst selected from the group consisting of Pt oxide, Pt halide, Pd oxide and Pd halide in the presence of an alcohol to cleave the one or more borane complexes and thereby obtain the compound of Formula (I) substantially free of any borane complex thereof; wherein: X is CH or N; R R each R each R each R each R carbocycle in R heterocycle in R each HetA is independently a 5- or 6-membered heteroaromatic ring containing from 1 to 3 heteroatoms independently selected from O and S, wherein the heteroaromatic ring is optionally fused with a benzene ring; wherein the optionally fused heteroaromatic ring is optionally substituted with from 1 to 4 substituents each of which is independently halo, —C each HetB is independently a 5- or 6-membered saturated or unsaturated heterocyclic ring containing from 1 to 4 heteroatoms independently selected from N, O and optionally oxidized S, wherein the heterocyclic ring is optionally fused with a benzene ring; and wherein the optionally fused heterocyclic ring is optionally substituted with from 1 to 7 substituents each of which is independently halogen, provided that the ring to which the halogen is attached is aromatic, —C s and t are each an integer equal to zero or 1, with the proviso that s+t=1 or 2.