I don't understand which logic leads from 'Oct 10 05:59:59'
to 'Oct 10 05:5[0-2]:'
but yes, you can put a datetime-string into a variable, dynamically manipulate this variable and use it as a pattern within any regex.
my $dt = 'Oct 10 05:59:59';
$dt =~ s/9:59$/[0-2]:/;
$file =~ m/$dt/;
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