Therapeutic compounds

Abstract

Compounds of formula (I) or salts thereof are disclosed. Also disclosed are pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for treating a Retroviridae viral infection including an infection caused by the HIV virus.

1 - 54 . (canceled) 
     
     
         55 . A process for preparing a compound of formula I: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, the process comprising:
 reacting a compound of formula (4) 
 
       
         
           
           
               
               
           
         
       
       or a salt thereof, with a compound of formula (5) 
       
         
           
           
               
               
           
         
       
       or a salt thereof, wherein R 1  is an amine protecting group and X 1  is a halogen, with a palladium catalyst and a weak base to produce a compound of formula (6) 
       
         
           
           
               
               
           
         
       
       or a salt thereof;
 treating the compound of formula (6), or a salt thereof, with a deprotecting agent to produce a compound of formula (7) 
 
       
         
           
           
               
               
           
         
       
       or a salt thereof; and
 reacting the compound of formula (7), or a salt thereof, with a compound of formula (8) 
 
       
         
           
           
               
               
           
         
       
       or a salt thereof, a peptide coupling agent, and a non-nucleophilic base, to produce the compound of formula (I). 
     
     
         56 . The process of  claim 55 , wherein R 1  is tert-butyloxycarbonyl (Boc). 
     
     
         57 . The process of  claim 55 , wherein the palladium catalyst is dichlorobis(tricyclohexylphosphine)palladium (II). 
     
     
         58 . The process of  claim 55 , wherein the weak base is sodium bicarbonate. 
     
     
         59 . The process of  claim 55 , wherein the deprotecting agent is trifluoroacetic acid. 
     
     
         60 . The process of  claim 55 , wherein the peptide coupling agent is 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU). 
     
     
         61 . The process of  claim 55 , wherein the non-nucleophilic base is diisopropylethylamine (iPr 2 NEt). 
     
     
         62 . The process of  claim 55 , wherein X 1  is Br. 
     
     
         63 . The process of  claim 55 , comprising preparing the compound of formula (4), or a pharmaceutically acceptable salt thereof, the process comprising:
 reacting a compound of formula (1)   
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein X 2  and X 3  are each independently a halogen, with methyl hydrazine to form a compound of formula (2) 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof;
 reacting the compound of formula (2), or a pharmaceutically acceptable salt thereof, with bis(pinacolato)diborane to form a compound of formula (3) 
 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof; and
 reacting the compound of formula (3), or a pharmaceutically acceptable salt thereof, with methanesulfonylchloride to form the compound of formula (4), or a pharmaceutically acceptable salt thereof. 
 
     
     
         64 . The process of  claim 63 , wherein X 2  is Br. 
     
     
         65 . The process of  claim 63 , wherein X 3  is F.