Roberto Bautista Agut followed two sprints with a gruelling slog as he battled past Karen Khachanov to reach the final of the Qatar Open.

Spanish second seed Bautista Agut had dashed past Andy Murray and Alejandro Davidovich Fokina for the loss of just three games in Doha, but Khachanov proved far more obdurate.

After a slow start, eventually Bautista Agut picked up the pace and emerged a 2-6 6-3 7-5 winner in two hours and 24 minutes of toil, earning a shot at Georgia's Nikoloz Basilashvili in Saturday's final.

Bautista Agut praised Russian Khachanov for making him scrap for the win.

"He was playing very fast," said Bautista Agut, quoted on the ATP website. "He was playing very solidly, he was defending very well and he hit many unbelievable passing shots. I had to play incredibly well tonight. I enjoyed tonight so much."

Third seed Basilashvili is the defending champion this week and made light work of France's Arthur Rinderknech, tying up a 6-4 6-2 victory.

In Marseille, Greek top seed Stefanos Tsitsipas was stunned by Russian qualifier Roman Safiullin in the Open 13 quarter-finals. World number 163 Safiullin had a staggering 13 break points against the under-performing Tsitsipas serve, and although 11 of those were saved, the two that were not decided the match.

Safiullin, for his part, faced one break point and saved it on the way to a 6-4 6-4 victory. He made his presence felt at the ATP Cup in Australia at the start of the year and, although results have been disappointing since, the 24-year-old is doing well again in France this week.

Next for Safiullin will be last week's Rotterdam champion Felix Auger-Aliassime, who saw off Belarusian Ilya Ivashka 6-3 6-4 in the last match of the day. After losing his first eight finals on the ATP Tour, Auger-Aliassime may well be closing in on a second title in eight days.

Saturday's other semi-final will see Russian second seed Andrey Rublev tackle Frenchman Benjamin Bonzi, who reached the last four of a main-tour event for the first time by crushing Aslan Karatsev 6-1 6-3.

Rublev dug deep to edge out French wildcard and former top-10 player Lucas Pouille 6-3 1-6 6-2.

Andy Murray suffered one of the heaviest losses of his career in the second round of the Qatar Open, while Andrey Rublev escaped an early exit at the Open 13. 

Former world number one Murray went down 6-0 6-1 to last year's runner-up Roberto Bautista Agut in Doha on Wednesday. 

It was just the fourth occasion in which the three-time major champion has lost a match while winning only one game or fewer in his career – the last time being a defeat by the same scoreline to Roger Federer at the ATP Finals in 2014. 

Murray's fellow Briton Dan Evans also endured a second-round loss, going down 4-6 7-5 6-4 to Alejandro Davidovich Fokina – Bautista Agut's next opponent. 

Denis Shapovalov bounced back from his first-round loss to Jiri Lehecka in Rotterdam last week by dropping just eight points on serve as he claimed a 6-4 6-0 victory over Alex Molcan inside 52 minutes. 

Next up for the Canadian will be Arthur Rinderknech after the Frenchman came from a set down to defeat seventh seed Alexander Bublik 6-7 (5-7) 6-1 6-4. 

Nikoloz Basilashvili faced little trouble in overcoming Elias Ymer 6-4 7-5 and his reward is a quarter-final against Marton Fucsovics, who got the better of Kwon Soon-woo. 

Karen Khachanov and Marin Cilic will meet in the last eight after they respectively eliminated Emil Ruusuvuori and Botic van de Zandschulp. 

In Marseille, second seed Rublev was made to work hard for a place in the Open 13 quarter-finals by home hope Richard Gasquet. 

Gasquet went a break up in the third set and, after surrendering his advantage, stopped Rublev serving out the match to force a tie-break. 

However, the world number seven did not waste his next opportunity as he sealed a 4-6 6-4 7-6 (7-3) success. 

Aslan Karatsev also booked his place in the last eight, while there were wins for Frenchmen Benjamin Bonzi and Lucas Pouille too. 

Top seed Aslan Karatsev exited the Astana Open at the last-16 stage with a straight-sets defeat to Emil Ruusuvuori on Thursday.

World number 84 Ruusuvuori saved a set point in the first-set tie-break on his way to a 7-6 (8-6) 6-4 victory and will now face Ilya Ivashka for a place in the semi-finals.

There was nearly another upset as home hopeful Alexander Bublik, seeded second, had to recover from a set down to overcome Miomir Kecmanovic 2-6 6-3 7-5.

Carlos Taberner awaits Bublik in the next round after the Spaniard beat Egor Gerasimov 5-7 7-6(5) 7-5.

Kwon Soon-woo and James Duckworth saw off Dusan Lajovic and Filip Krajinovic respectively in straight sets to remain a course for glory.

At the Moselle Open in Metz, meanwhile, Gael Monfils took out Philipp Kohlschreiber 7-6(2) 6-4 to reach the quarter-finals on home soil.

Tournament favourite Hubert Hurkacz made light work of 2016 champion Lucas Pouille with a 6-2 6-3 victory to set up a meeting with Andy Murray in the quarter-finals.

Elsewhere on Thursday, German qualifier Peter Gojowczyk proved too strong for Karen Khachanov and will now face Marcos Giron, who upset fourth seed Alex de Minaur.

Lucas Pouille continues to build momentum at the Winston-Salem Open after overcoming veteran Feliciano Lopez in straight sets.

Pouille was on the brink of elimination in qualifying after facing match point before booking his spot in the main draw.

Now, the Frenchman is preparing for the second round following his 6-1 6-4 victory over Lopez on Monday.

Pouille saved all four break points he faced as the former world number 10 claimed his first ATP Tour-level victory since April's Monte Carlo Masters.

Awaiting Pouille in the second round is third seed Daniel Evans, who received a bye in the opening round.

As for 14th seed Richard Gasquet, he prevailed 7-6 (7-4) 7-6 (8-6) against Egor Gerasimov at the ATP 250 event.

Elsewhere, Federico Coria and Jordan Thompson were among the players to progress.

Pedro Martinez outlasted Lucas Pouille to set up a second-round clash with fellow Spaniard Roberto Bautista Agut at the Generali Open.

World number 97 Martinez came through Monday's longest match, which lasted two hours and 43 minutes, as a 6-3 6-7 (4-7) 6-4 winner.

Mikael Ymer, who reached the quarter-finals of last week's Swiss Open Gstaad, is also through to the second round in Austria after battling past Pablo Cuevas 6-3 7-5.

Qualifier Jozef Kovalik will face Jiri Vesely for a place in the quarter-finals, meanwhile, after beating ninth seed Jaume Munar in straight sets.

Also through on Monday was lucky loser Carlos Taberner, who took advantage of his second chance by battling from a set down to overcome Thiago Seyboth Wild 3-6 6-3 6-2.

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