CCN(C(C)C)C(C)C.[N:10]1([C:14]([C:16]2[CH:17]=[C:18]([Cl:38])[C:19]([O:22][C:23]3[CH:24]=[C:25]([CH:29]=[C:30]([O:32][C@@H:33]([CH3:37])[CH2:34][O:35][CH3:36])[CH:31]=3)[C:26](O)=[O:27])=[N:20][CH:21]=2)=[O:15])[CH2:13][CH2:12][CH2:11]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:63][C:64]1[S:65][CH:66]=[CH:67][N:68]=1>CN(C=O)C.O>[N:10]1([C:14]([C:16]2[CH:17]=[C:18]([Cl:38])[C:19]([O:22][C:23]3[CH:24]=[C:25]([CH:29]=[C:30]([O:32][C@@H:33]([CH3:37])[CH2:34][O:35][CH3:36])[CH:31]=3)[C:26]([NH:63][C:64]3[S:65][CH:66]=[CH:67][N:68]=3)=[O:27])=[N:20][CH:21]=2)=[O:15])[CH2:11][CH2:12][CH2:13]1DIPEA (0.129 mL) was added to a suspension of 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzoic acid (168 mg), HATU (190 mg) and 2-aminothiazole (40 mg) in DMF (2 mL) and the mixture stirred at RT for 16 hours. Water (30 mL) was added and the mixture extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with 50-100% ethyl acetate in isohexane, to give the desired compound (75 mg).
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