Southampton have submitted a deal sheet to the Premier League as they try to sign Liverpool forward Takumi Minamino on loan for the rest of the season.
The paperwork means Saints have two hours beyond the 23:00 GMT deadline to complete the transfer.
Minamino, 26, joined Liverpool in a £7.25m deal from Red Bull Salzburg in January 2020.
But he has been on the periphery at Anfield, making just four Premier League starts since his arrival.
Southampton turned to Minamino after being frustrated with other moves.
They had hoped to sign Arsenal’s Ainsley Maitland-Niles but talks broke down and he is joining West Bromwich Albion.
Meanwhile, Southampton’s French right-back Yan Valery, 21, has joined Championship side Birmingham on loan.