before succumbing to harsh conditions and hostile natives. A small band of survivors traveled eastward into the lands of the Caddo, but La Salle was killed by disgruntled expedition members. In 1690 Spanish authorities, concerned that France posed a competitive threat, constructed several missions in East Texas among the Caddo. After Caddo resistance, the Spanish missionaries returned to Mexico. When France began settling Louisiana, mostly in the southern part of the state, in 1716 Spanish authorities responded by founding a new series of missions in East Texas. Two years later, they created San Antonio as the first Spanish civilian settlement in the area. Hostile native tribes and distance from nearby Spanish colonies discouraged settlers from moving to the area. It was one of New Spain's least populated provinces. In 1749, the Spanish peace treaty with the Lipan Apache angered many tribes, including the Comanche, Tonkawa, and Hasinai. The Comanche signed a treaty with Spain in 1785 and later helped to defeat the Lipan Apache and Karankawa tribes. With more numerous missions being established, priests led a peaceful conversion of most tribes. By the end of the 18th century only a few nomadic tribes had not converted to Christianity. When the United States purchased Louisiana from France in 1803, American authorities insisted the agreement also included Texas. The boundary between New Spain and the United States was finally set at the Sabine River in 1819, at what is now the border between Texas and Louisiana. Eager for new land, many United States settlers refused to recognize the agreement. Several filibusters raised armies to invade the area west of the Sabine River. Marked by the War of 1812, some men who had escaped from the Spanish, held (Old) Philippines had immigrated to and also passed through Texas (New Philippines) and reached Louisiana where Philippine exiles aided the United States in the defense of New Orleans against a British invasion, with Filipinos in the Saint Malo settlement assisting Jean Lafitte in the Battle of New Orleans. In 1821, the Mexican War of Independence included the Texas territory, which became part of Mexico. Due to its low population, the territory was assigned to other states and territories of Mexico; the core territory was part of the state of Coahuila y Tejas, but other parts of today's Texas were part of Tamaulipas, Chihuahua, or the Mexican Territory of Santa Fe de Nuevo México. Hoping more