Awkward getting some sleep in it (5)
I believe the answer is:
inapt
'awkward' is the definition.
('inapt' can be a synonym of 'awkward')
'some sleep in it' is the wordplay.
'some sleep' becomes 'nap' ('nap' can be a synonym of 'sleep').
'in' indicates putting letters inside.
'nap' placed into 'it' is 'INAPT'.
'getting' acts as a link.
(Other definitions for inapt that I've seen before include "Improper" , "Free from deceit" , "unqualified" , "Ill-chosen, not suitable" , "not fit for purpose" .)