I do not have a HR50 but looking at the user manual you could use EXTTR RCA style jack on the HL2 for your PTT signal to the HR50 PTT RCA style jack, or run it to pin 4 of the HR50 DB9.
If you want the HL2 PTT signal (GND=TX) to travel though the IOBoard DB9 cable instead, then you can jumper EXTTR to the IOBoard DB9. More exotic ways involve using a IOBoard GPIO_out pin with code added to follow EXTTR state. The example code already has an interrupt function called when ever GPIO113_EXTTR changes state.
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