CHARLESTON, Mo. (AP) — A southeastern Missouri city has agreed to pay $500,000 to settle its part in a lawsuit brought by the family of a Black man who died in jail after having his neck pinned down for several minutes by the knee of a white sheriff.

A federal judge said Wednesday that she would likely approve the settlement between the mother, widow and nine children of Tory Sanders and the city of Charleston and several of its police officers, the St. Louis Post-Dispatch reported. The family’s lawsuit is still pending against Mississippi County, the former sheriff and jail staffers.

Sanders’ 2017 death has drawn comparisons to last May’s death of George Floyd in Minneapolis after a white police officer pinned down the handcuffed Black man’s neck for several minutes. That officer, who was later fired, is standing trial in Floyd’s death.

In the Missouri case, Sanders was on his way to Nashville when he went to police in Charleston on May 4, 2017, to say he needed psychiatric help. He was taken to the Mississippi County Jail, where a mental health counselor determined that Sanders was suffering from paranoia and recommended he be hospitalized for observation. But Sanders remained in the jail, and hours later, then-Sheriff Cory Hutcheson led a team of officers and jailers into Sanders’ cell, where Sanders was tackled, pepper sprayed, shocked with a stun gun and beaten, according to the lawsuit.

Sanders’ family says Hutcheson pressed his left knee into Sanders’ neck and kept it there for up to three minutes, even as a police officer urged him to stop. Missouri’s previous and current attorneys general both investigated Sanders’ death but declined to bring charges.

Hutcheson was later sentenced to six months in federal prison for the unrelated crimes of wire fraud and identity theft for using a fraudulent process to track the whereabouts of more than 200 cellphone users, including a judge and a former sheriff. He resigned after pleading guilty and can no longer work in law enforcement.

Sanders’ death, in part, led the state’s NAACP chapter in 2017 to issue a Missouri “travel advisory” over concerns about whether civil rights would be respected for those traveling through the state.

Charleston is in southeastern Missouri just west of the southern tip of Illinois.