I wonder if this synthesis I attach could be acceptable. First, I'm not sure the step 1 could be possible, I mean, I'm not sure that the amine group wouldn't react with the SOCl2 too.
If that step is correct and the product 2 is formed, then I thought that the amine could react with the acyl chloride formed to form an amide... but I hope that won't happen due to the steric hindrance of that possible product.
If that is correct, I think the synthesis may work...
Hope you can help me, thanks a lot!