FC(F)(F)C(O)=O.C([CH:15]1[CH2:20][NH:19][CH2:18][CH2:17][N:16]1[C:21]1[C:26]([NH:27][CH:28]([CH3:30])[CH3:29])=[CH:25][CH:24]=[CH:23][N:22]=1)(OC(C)(C)C)=O.C([O-])([O-])=O.[K+].[K+].O>ClCCl>[N:16]1([C:21]2[C:26]([NH:27][CH:28]([CH3:30])[CH3:29])=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:15][CH2:20][NH:19][CH2:18][CH2:17]1Trifluoroacetic acid (2.0 mL) was added to a stirred solution of 2-(Boc-piperazinyl)-3-(i-propylamino)pyridine 4 (1.426 g, 4.45 mmol) in dichloromethane (10 mL) at 0° C. The resulting mixture was stirred at 0° C. for 30 min, at room temperature for 1 h 15 min. Additional quantities of TFA (2.0 mL) were added. The mixture was stirred at room temperature for another 23 h. Sat. K2CO3 solution was slowly added to quench the reaction (gas ↑). Small amount of water was added to help the layers separation. The organic phase was separated and the aqueous phase was extracted with dichloromethane (2×25 mL). The combined organic solution was washed with brine, dried over anhydrous Na2SO4, and concentrated to afford the product in quantitative yield. 1H-NMR (CDCl3): 7.681 (dd, J=5.0 Hz and 1.5 Hz, 1H, Ar—H), 6.890 (dd, J=8.0 Hz and 5.0 Hz, 1H, Ar—H), 6.800 (dd, J=8.0 Hz and 1.5 Hz, 1H, Ar—H), 4.170 (d, J=7.5 Hz, 1H, NH), 3.567-3.485 (m, 1H, CH), 3.046 (s, 8H, 4 CH2), 1.983 (br, 1H, NH), 1.234 (d, J=6.0 Hz, 6H, 2 CH3).
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