On the authority of Abdullah ibn Amr, that the Messenger of Allah, peace and blessings be upon him, used to say: "Three people whose prayer Allah does not accept: a man who leads a people while they dislike him, a man who comes to prayer after its time has passed—and 'after its time' means that he comes to it after it has escaped him—and a man who enslaves a freed person."(1)

‌‌65 - Chapter: Leading the Blind in Prayer
595 - Muhammad ibn Abd al-Rahman al-Anbari Abu Abdullah narrated to us, Ibn Mahdi narrated to us, Imran al-Qattan narrated to us, on the authority of Qatada--------------------------------------------
(1) Its chain is weak: Abd al-Rahman ibn Ziyad—who is al-Ifriqi—and Imran al-Qattan are both weak, while the rest of its narrators are trustworthy. Al-Qa'nabi: he is Abdullah ibn Maslama.
It was also recorded by Ibn Majah (970) via the chain of Abd al-Rahman ibn Ziyad, with this chain. On this topic, from Ibn Abbas, recorded by Ibn Majah (971), with the wording: "Three people whose prayers do not rise above their heads by a span: a man who leads a people while they dislike him, a woman who spends the night while her husband is angry with her, and two brothers who have cut ties with each other." Its chain is good, and Ibn Hibban declared it authentic (1757).
And from Abu Umama, recorded by al-Tirmidhi (360), with a weak chain.
Note: In the Syrian edition, edited by Izzat al-Da'as, the following appears after this hadith:

‌‌64 - Chapter: Leading the Pious and the Wicked in Prayer
594 - Ahmad ibn Salih narrated to us, Ibn Wahb narrated to us, Mu'awiya ibn Salih narrated to me, on the authority of al-Ala ibn al-Harith, on the authority of Mak-hul, on the authority of Abu Hurayra, who said: The Messenger of Allah, peace and blessings be upon him, said: "The obligatory prayer is incumbent behind every Muslim, whether pious or wicked, even if he commits major sins."
This hadith appeared only in the margin of (J). It will come in full in the Book of Jihad, number (2533). Al-Mizzi attributed it in "Tuhfat al-Ashraf" (14619), and al-Zayla'i in "Nasb al-Raya" 2/27, only to the Book of Jihad.
And Sheikh Abd al-Ghani al-Nabulsi said in the margin of his copy, after mentioning this hadith: It appears in the copy of Humayd ibn Thawaba, the narrator from Abu Isa al-Ramli. We did not find it in the copies of Abu Dawud, and for this reason we did not append it to the original.