Example 70
The mixture of compound 75-1 (50 mg, 0.15 mmol, 1 eq), DIEA (30.6 mg, 0.23 mmol, 41.3 uL, 1.5 eq) and HATU (90.1 mg, 0.23 mmol, 1.5 eq) in DCM (1 mL) was stirred at 25° C. for 1 hr. Then tert-butyl N-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate (53.1 mg, 0.15 mmol, 1 eq) was added at the mixture and the mixture was stirred at 25° C. for 1 hr. LC-MS and HPLC showed the desired compound was detected. The reaction mixture was diluted with H2O (10 mL) and the mixture was extracted with EA (10 mL*3). The combined organic phase was washed with brine (10 mL*3), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC. The title compound (25 mg, 39.3 umol, 24.9% yield) was obtained as yellow oil. LCMS (ESI): RT=0.886 min, mass calc. for C33H41F3N2O7 634.68, m/z found 657.1 [M+Na]+; 1H NMR (400 MHz, CD3OD) δ 1.43 (s, 9H), 3.18 (t, J=5.52 Hz, 2H), 3.44 (t, J=5.52 Hz, 2H), 3.49-3.54 (m, 2H), 3.54-3.59 (m, 2H), 3.59-3.63 (m, 2H), 3.64-3.68 (m, 4H), 3.69 (s, 3H), 3.71-3.76 (m, 2H), 7.59 (d, J=7.03 Hz, 1H), 7.64-7.74 (m, 3H), 7.81-7.94 (m, 4H), 8.09 (d, J=8.28 Hz, 1H), 8.51 (s, 1H).
