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645 – 668
The Goguryeo–Tang War occurred from 645 to 668 and was fought between Goguryeo and the Tang dynasty. During the course of the war, the two sides allied with various other states. Goguryeo successfully repulsed the invading Tang armies during the first Tang invasions of 645–648. After conquering Baekje in 660, Tang and Silla armies invaded Goguryeo from the north and south in 661, but were forced to withdraw in 662. In 666, Yŏn Kaesomun died and Goguryeo became plagued by violent dissension, numerous defections, and widespread demoralization. The Tang–Silla alliance mounted a fresh invasion in the following year, aided by the defector Yŏn Namsaeng. In late 668, exhausted from numerous military attacks and suffering from internal political chaos, Goguryeo and the remnants of Baekje army succumbed to the numerically superior armies of the Tang dynasty and Silla.
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645
The first conflict of the Goguryeo–Tang War started when Emperor Taizong of the Tang dynasty led a military campaign against Goguryeo in 645 to protect Silla and punish Generalissimo Yŏn Kaesomun for the killing of King Yeongnyu. The Tang forces were commanded by Emperor Taizong himself, and generals Li Shiji, Li Daozong, and Zhangsun Wuji.
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The Battle of Mount Jupil, also known as Battle of Jupil-san and Battle of Mount Zhubi was a battle between Tang Chinese and Goguryeo Korean forces that took place in Mount Jupil at the south of the fortress city of Ansi. It took place on July 11, 645 AD. The small but elite Tang army wiped out the Goguryeo relief force trying to come to bolster the defenses of Ansi, achieving a major victory.