Cat will not stop yelling at me to feed him

I have a cat, Calvin, getting up there in years (13). He's healthy and happy but I've unfortunately encouraged a bad habit and had to switch him from free-feeding to set meal time about a year ago.

Bad habits: He's gotten more and more talkative over the last 5 years. He comes when I call him and usually talks back to me, which I thought was fun so we would have long conversations talking back and forth with each other. This used to be cute when it only happened when I talked back at him. (take-away: I've reinforced that yowling at humans is a great way to gain their attention)

Changes: I switched from free-feeding to 3X daily feeding about a year ago. Mainly a consideration for my other cat who takes medication in his food. This situation also means the two cats have to be fed separately.

Problem: He never really got used to not having a constant supply of food. If I'm in the kitchen (where he's fed) he will stand by the food-area and yell at me almost constantly. He will also start yelling about a half hour before meal time (6:00AM). It is not cute, he is very loud and persistent and I live in a duplex. I'm sure it's obnoxious for the neighbors, too.

I know you're supposed to just ignore unwanted behavior like this. How can I do that?? He follows me around the house an hour before meal time yelling. I try waiting for him to settle down and get distracted, but if I move towards the food he starts up again. I can't use an auto-feeder because he must be fed separately from the cat requiring medication. So I'm not sure how to break this "Yell at human --> Food" reward cycle.

Any tips for this situation? Maybe I just really need to figure out another way to give the other cat his medicine and start using an auto-feeder.