Arsenal appear unlikely to complete the signing of Monaco forward Thomas Lemar, meaning Manchester City's bid to sign Alexis Sanchez also looks destined to fail.
Some reports suggest Arsenal offered as much as £92million for France international Lemar, but Press Association Sport understands the Gunners are now not expecting to get the deal over the line before the 2300 BST deadline.
Lemar, 21, has been a target of Arsenal boss Arsene Wenger for much of the summer, with Liverpool also interested in him.
It is understood the Gunners made a late push to sign Lemar after Manchester City made them an improved offer for Chile forward Sanchez.
While Wenger has been insisting for months that Sanchez, whose contract expires at the end of the season, would not be sold, it is believed he would have had a chance of a move if Arsenal could have signed a replacement.
But their failure to land Lemar ultimately means Sanchez is likely to stay put, even though it is understood City launched an improved bid earlier on Thursday.