Your portable player probably only supports a limited number of formats. Just because you can play something on your PC doesn’t mean you can necessarily play it on your 5285.
It is in some cases possible to upgrade such players to play other formats, but it’s usually in the form of firmware upgrades and quite rare.
The best thing to do would be to upload another video in a format your player supports, or convert the video you wanted to add to such a format.
According to the manual, which I got
here, your player should have come with a program named MediaConverter™ (Section 8, technical data). That’s probably what you should be using to convert your video.
Misc debris: The manual says the player supports MPEG-4 SP (Simple Profile), but it doesn’t elaborate (like what container or fourcc - there’s tons of implementations of MPEG-4 out there). You can probably find out by checking out what’s produced by MediaConverter though. It also says it supports Windows Media Video 9 (with certain restrictions on resolution and bitrates) - you can easily create or convert to WMV9 using Windows Media Encoder or Windows Movie Maker.