(AP) — By the time the U.S. Supreme Court refused a last-minute stay of execution for Herbert Smulls, the Missouri inmate was already dead. His attorneys say it was the third straight time a Missouri inmate has been executed with an appeal pending.

Late Wednesday, attorneys for Smulls made one last appeal to the Supreme Court. It had already ruled hours earlier that the execution could proceed.

Smulls’ attorney Joseph Luby says the stay was denied at 10:24 p.m., four minutes after Smulls was pronounced dead.

Missouri Attorney General Chris Koster says in a statement that the Supreme Court has ruled that pending litigation is not sufficient to stop an execution. He says the state directly asked the high court if the execution should be stayed, and was told no.