FR 7913 then FR 6410 at Madrid
Milan → Madrid → Sofia
Timetable, Madrid time
11:10FR 7913 from Milan at the gate
06:00FR 6410 to Sofia leaves the gate
18 h 50 apart on the timetable, overnight
FR 6410 leaves 18 h 50 after FR 7913 arrives on the timetable: more than half a day, so not a connection we count.