PORTLAND, Ore. (KOIN) — Federal agents fired tear gas, pepper balls and flashbangs at demonstrators in downtown Portland during the 54th straight night of protests on Tuesday.

Officers made their first appearance of the night at about 11:10 p.m. and immediately started using crowd-control munitions in an attempt to disperse hundreds of people gathered outside of the Multnomah County Justice Center and Mark O. Hatfield Federal Courthouse on SW 3rd Avenue. Protesters reportedly equipped with hammers and crowbars, donned in helmets and gas masks had begun kicking and pounding on plywood covering the exterior of the Portland Police Bureau Central Precinct and the federal courthouse.

Police say the group breached the west side doors of the federal courthouse shortly after 11 p.m., prompting the federal officers’ response. Another group of federal officers marched down SW 4th and stopped outside of City Hall. It’s unclear what prompted them to stop at that location.

As Tuesday’s protests spilled into Wednesday morning, police say protesters gathered fences and road barricades and began approaching the federal courthouse, using pieces of the fence as a shield. Officers identified over a loud speaker as being from the Federal Protective Service then deployed gas and other crowd-control munitions to push remaining protesters away from the federal courthouse.

An announcement then said the situation had been declared an “unlawful assembly”.

Around 1:30 a.m.multiple fires were set in the area — including one outside an exit door of the federal courthouse. At 1:45 a.m., federal officers once again rushed against protesters, deploying clouds of tear gas and other munitions in an effort to disperse the crowd. Meanwhile, another fire was lit at Lownsdale Square Park.

The remaining crowd slowly thinned out within the next hour or so.

Portland police say they did not engage with protesters at all overnight and made no arrests. It is not clear how many arrests were made by federal officers.

Earlier in the day, the “Wall of Moms” (and dads) gathered at Salmon Street Springs Park before marching to the Justice Center area in an effort to protect younger protesters.

“We’re just moms that are tired of seeing other community members get hurt,” one mom named Heather told KOIN 6 News. The moms made their first coordinated appearance at the protests last weekend and have been welcomed into the fold by demonstrators, as has the group of dads that showed up Monday night.

The moms have been trying to separate protesters and the federal officers, as well as helping people wash their eyes and recover from exposure to tear gas. Their close proximity to the action means they’re often the first to feel the effects of crowd-control munitions.

“Coming out, you kind of know what to expect in a way,” said Courtney, another mom. “But it’s nothing compared to childbirth.”

Here is a running list of events from Tuesday night, July 21:

1:45 a.m.

A fire was lit at Lownsdale Square Park as federal officers rushed the protesters once again, dispersing the crowd.

The rest of the protesters slowly dissipated over the next few hours, police say.

1:30 a.m.

Just before 1:30 a.m., protesters reportedly set a fire outside one of the exits of the federal courthouse. A large portion of plywood was torn from the building as well.

1:00 a.m.

Police say a fire hydrant was opened by protesters around 1 a.m. A few people reportedly added soap to the water. Small fires were lit around the area as demonstrators continued to spray paint graffiti onto city, state and federal property, according to police.

12:45 am:

Officers identified over loud speaker as being from the Federal Protective Service have deployed gas and other crowd-control munitions to push remaining protesters away from federal courthouse. The announcement says the situation has been declared an “unlawful assembly”.

Police say protesters gathered fences and road barricades and began approaching the federal courthouse, using pieces of the fence as a shield.

11:10 p.m.

Federal officers marched down SW 4th Avenue and stopped in front of City Hall. More officers started using tear gas, pepper balls and other crowd-control munitions at the federal courthouse as officers attempted to push the crowd to the west.

Police say protesters were running “aggressively” toward one side of the federal courthouse during this.

11 p.m.

Protesters reportedly equipped with hammers, crowbars and other pry tools, donned in helmets and gas masks began kicking and pounding on plywood covering the exterior of the federal courthouse. Police say the group breached the west side doors of the Federal Courthouse shortly after 11 p.m.

10:40 p.m.

Protesters reportedly dragged a large metal fence around to the side of the federal courthouse while others started to kick the doors of the Justice Center.

9 p.m.

More than 1,000 people have gathered outside of the federal courthouse and the Justice Center. Many are with the “Wall of Moms” group, chanting slogans calling for the removal of “racist cops” from law enforcement agencies.

More than 1,000 people turned out for Monday night’s demonstrations, the largest crowd seen downtown in weeks. Federal officers began launching tear gas, flash bangs, and pepper balls just before 12:30 a.m. Tuesday. The Portland Police Bureau said demonstrators had attempted to break into the federal courthouse, prying back plywood while donned in helmets, gas masks and shields. People reportedly used crowbars and other tools to penetrate the makeshift wooden exterior, breaking at least one glass window, before being rushed by federal law enforcement.

Clashes continued for about an hour before federal officers retreated. Small fires were lit at the Federal Courthouse and County Courthouse later on, drawing Portland Fire and Rescue to the scene and sparking additional responses from federal police.

Officers arrested five people on charges including assault on a federal officer, failure to comply, trespass, and creating a disturbance. A sixth person was detained and given a misdemeanor citation, according to a spokesperson for the United States Attorney’s Office.