I'm familiar with 3.5 and Pathfinder and the ability to tie up a grappled target on a roll check and doing so while pinned up. Well, our DM refuses to allow grappling due to the fact it is an unwilling target and rounds only last 6 seconds. Unfortunately there aren't any rules on it but the argument that a round is 6 seconds and it's an unwilling target seems to be the silliest reason not to be able to roll to tie up a grappled target.
Any opinions or insight possibly from a rules standpoint?
This is the 5th edition forum... not sure if this is a 5th edition question or not...
But in 5e, you can knock creatures out easily enough. Then tie them up.
For better or worse, it's the DM's call. For manacles, you can refer them to http://www.sageadvice.eu/?s=manacle
There aren't any official rules that I know of for tying someone up. As mellored pointed out, you can knock them out.
These are the relevant rules:
Grappling, Basic Rules, page 74.
Rope, Basic Rules, page 50.
Net, Basic Rules, page 47.
Grappled Condition, Basic Rules, page 106.
This would be my ruling:
Yes, short of any additional context that would complicate the matter further than the standard resistance to the attempt one might expect in a combat situation, you can try to tie up a grappled enemy. Grappling means grabbing or wrestling a creature, preventing their moving around the battlefield. An attempt to tie up the target would likely result in a contest with ability checks appropriate to the player's approach and the enemy's attempt to resist it. A character might have advantage if the rope is fashioned into a lasso. If the player prevails in the contest, the enemy is restrained (Basic Rules, page 106).
But your DM may make a different ruling based on different criteria and still be acting within his or her role.
iserith wrote:
Noctaem wrote:
You can also just threaten to keep hitting them uless they allow themselves to be tied up.
A character with the Grappler feat could pin the opponent, rendering him Restrained.
If your DM questions the realism of effectively tying up a grappled creature in under six seconds, invite them to google "calf roping videos". 
Doomaflatchi wrote: