Set right after 4.11. Don't own 'em.
He does try to sleep, but he can't stop thinking about them. The people dying out there, while he just lies here idly. He failed three people today and he can't stop thinking about that, either. So he clambers stiffly out of bed and boots up the computer.
And he's suddenly reminded of Sam, long ago. Wasted and desperate, grieving for a man he'd never met.
"The more people I save...."
He'd marvel at the repetition, except it's not that similar.
Because Sam had still been hoping to be saved. For Dean, it is long too late.