Process for preparing quinoline compounds and products obtained therefrom

Abstract

Methods for synthesizing tetrahydroquinoline-containing compounds are provided, along with synthetic intermediates and products associated with such methods.

1 - 56 . (canceled) 
   
   
       57 . A compound having formula: 
     
       
         
         
             
             
         
       
       wherein X is a counterion of an acid having a pKa less than 1. 
     
   
   
       58 . The compound of  claim 57  wherein X is Cl. 
   
   
       59 - 67 . (canceled) 
   
   
       68 . A composition comprising:
 a) a compound of formula G:   
     
       
         
         
             
             
         
       
       and 
       b) one or more organic impurities in a total amount of about 2 area percent HPLC or less, or one or more residual solvents in a total amount of 1.0 weight percent or less, or combinations thereof. 
     
   
   
       69 . The composition of  claim 68  wherein compound G is present in an amount of at least about 96.5 weight percent on an anhydrous basis, based on the total weight of the composition. 
   
   
       70 . (canceled) 
   
   
       71 . The composition of  claim 68  wherein the organic impurities or residual solvents comprise at least one of the dimer compound, or a salt thereof, or ethanol. 
   
   
       72 . The composition of  claim 68  wherein the single largest organic impurity is present in an amount of about 0.6 area percent HPLC or less. 
   
   
       73 . (canceled) 
   
   
       74 . The composition of  claim 68  wherein the total residual solvents are present in an amount of 0.5 weight percent or less. 
   
   
       75 . The composition of  claim 74  wherein the residual solvent comprises ethanol. 
   
   
       76 . A composition comprising
 a) a compound of formula G:   
     
       
         
         
             
             
         
       
       and 
       b) water in an amount of about 2.0 weight percent or less, based on the total weight of the composition. 
     
   
   
       77 . A compound of formula G: 
     
       
         
         
             
             
         
       
       in the form of needle shaped crystals. 
     
   
   
       78 . The compound of  claim 77  wherein the needle shaped crystals are reduced to have an aspect ratio of less than about 3. 
   
   
       79 . A compound of formula G: 
     
       
         
         
             
             
         
       
       having a median particle size of less than about 25 microns. 
     
   
   
       80 . The compound of  claim 79  wherein 90% of the particles have a particle size of less than about 70 microns. 
   
   
       81 . A composition comprising a compound of formula G: 
     
       
         
         
             
             
         
       
       wherein the hydrogen chloride content is from about 12.8 weight percent to about 14.8 weight percent as measured by ion chromatography, based on the total weight of the composition. 
     
   
   
       82 . The composition of  claim 81  wherein the compound of formula G has a chiral purity of at least about 99.5 area percent HPLC in the composition.