Saddled with $20.6 billion of debt, IHeart, formerly called Clear Channel Communications Inc., is working on a deal that would retire about $1.4 billion of its most-pressing obligations before 2019, some trading at less than 39 cents on the dollar, according to a person with direct knowledge of the matter. The plan marks the company’s latest attempt to rein in the debt it took on in its 2008 acquisition by private equity firms Bain Capital Partners LLC and Thomas H. Lee Partners LP, a $24 billion deal that came to symbolize the excesses of the per-crisis buyout boom.

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