CCN(C(C)C)C(C)C.[I:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=O.CN(C(ON1N=NC2C=CC(Cl)=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:45][C:46]([F:56])([F:55])[O:47][C:48]1[CH:54]=[CH:53][C:51]([NH2:52])=[CH:50][CH:49]=1>C1COCC1.CC#N>[I:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([NH:52][C:51]1[CH:53]=[CH:54][C:48]([O:47][C:46]([F:45])([F:55])[F:56])=[CH:49][CH:50]=1)=[O:16]DIPEA (6.34 mL, 36.3 mmol) was added to a solution of 3-iodobenzoic acid (3 g, 12.1 mmol) and 2-(6-chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU, 5.50 g, 13.31 mmol) in THF (25 mL) and MeCN (5 mL) and the RM was stirred at RT for 1 h. 4-(Trifluoromethoxy)aniline (2.435 mL, 18.14 mmol) was then added and the RM was stirred at RT for 3 h. The solvent was evaporated off under reduced pressure and the residue was treated with aq. HCl (50 mL of 1 M) and extracted with TBME/EtOAc (9:1). The combined extracts were washed with aq. 1 M HCl, sat. aq. Na2CO3 (50 mL), water and brine, dried over MgSO4 and the solvent was evaporated off under reduced pressure. The residue was suspended in water, filtered and dried to afford the title compound as a purple solid. UPLC-MS (Condition 1) tR=3.23 min, m/z=407.8-409.8 [M+H]+, m/z=405.9-406.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.33-7.41 (m, 3H) 7.88 (d, J=9.3 Hz, 2H) 7.94-8.00 (m, 2H) 8.30 (t, J=1.7 Hz, 1H) 10.50 (s, 1H).
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