Patent ID: 9388147
Filing Date: 2016-07-12
CPC Classification: A61K,A61P,C07C,C07D

Claim Text:
1. A method for the synthesis of a compound comprising an indane moiety having a chiral carbon in the five-membered ring of the indane moiety where the compound is enantiomerically enriched with respect to the chiral carbon, wherein the compound is the method comprising the steps of: (i) providing an indane moiety where the ring carbon of the five-membered ring of the indane moiety where chiral substitution is desired is oxo substituted at such carbon, the compound having the following structure: (ii) reacting the compound of step (i) with a chiral reagent, wherein the chiral agent is a chiral sulfinamide of the form RS(═O)NH (iii) forming a chiral center at the indane moiety carbon previously bound to the oxo group by reacting the compound of step (ii) with a reducing agent, thereby forming a compound of one of the following structures: (iv) converting the compound of step (iii) to a chiral amine, thereby forming a compound of one of the following structures: (v) reacting the compound of step (v) with an activated substituted alkyl group, a compound of one of the following structures where P is a protecting group; (vi) reacting the compound of step (v) with an activated substituted alkyl group, thereby forming a compound of one of the following structures where R″ is a substituted alkyl group;  and (vii) treating the compound of step (vi) with a hydroxylamine or a hydroxylamine hydrochloride to convert the cyano substituent to a hydroxyamidine at the 4-position of the indane moiety, thereby forming a compound of one of the following structures: