I am a little confuse with how do we perform signed 2's complement multiplication.
10 1101 -19
x 11 0001 x -15
---------------- ------
101101 285
000000
000000
000000
101101
101101
----------------
100010011101
Adding all the calculations I get "100010011101" as stated which is not 285 signed, why?
You're doing unsigned arithmetic. To do two's complement, you need to treat the numbers as having infinitely repeating sign digits:
...1111101101
...1111111001
-------------------------
...1111101101
...0000000000
...0000000000
...0000000000
...1111101101
...1111101101
...1111101101
...1111101101
...1111101101
...1111101101
:
-------------------------
...0000000100011101
And you need to continue the process until it reaches a fixed point (where further bits computed will all be the same.) It turns out that this will always happen by the time you produce n+m bits of output (where n and m are the sizes of the multiplicands in bits), so this is easily bounded.