CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][CH:26]([F:56])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:52])[C:37]2[CH:42]=[C:41]([CH2:43][NH:44][C:45]([C:47]([CH3:50])([CH3:49])[CH3:48])=[O:46])[CH:40]=[CH:39][C:38]=2[Cl:51])=[CH:31][C:30]=1[C:53]([OH:55])=O.[Cl:57][C:58]1[CH:59]=[C:60]([CH:62]=[CH:63][C:64]=1[F:65])[NH2:61]>C1COCC1>[F:25][CH:26]([F:56])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:52])[C:37]2[CH:42]=[C:41]([CH2:43][NH:44][C:45]([C:47]([CH3:50])([CH3:49])[CH3:48])=[O:46])[CH:40]=[CH:39][C:38]=2[Cl:51])=[CH:31][C:30]=1[C:53]([NH:61][C:60]1[CH:62]=[CH:63][C:64]([F:65])=[C:58]([Cl:57])[CH:59]=1)=[O:55]HATU (43 mg, 0.11 mmol) was added to N-[4-(2,2-difluoroethyl)oxy-3-hydroxycarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide (50.0 mg, 0.107 mmol) in 5.0 mL THF, followed by 52 μL TEA and the mixture was stirred for 15 min. Then 3-chloro-4-fluoroaniline (15.5 mg, 0.107 mmol) was added and it was stirred for 4 h at rt. The crude mixture was concentrated, EtOAc was added and the organic phase was washed with satd. aq. NaHCO3-solution, water and satd. NaCl-solution. The organic phase was dried with Na2SO4 and concentrated i. vac. to give the title compound.
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