Cl[CH2:2][C:3]1[N:4]=[CH:5][S:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(Cl)Cl.CCOC(C)=O>[S:6]1[CH:7]=[C:3]([CH2:2][N:27]2[CH2:26][CH2:25][N:24]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:29][CH2:28]2)[N:4]=[CH:5]1
4-(Chloromethyl)thiazole (0.500 g, 2.94 mmol, 1 eq) was suspended in DCM (4.6 mL). DIPEA (1.28 mL, 7.35 mmol, 2.5 eq) was added dropwise, followed by N-Boc-piperazine (1.200 g, 6.47 mmol, 2.2. eq). The mixture was stirred at 35° C. for 5 h, diluted with EtOAc and washed with H2O and brine. The organic layer was separated, dried (MgSO4) and the solvent was removed in vacuo. The crude product was purified by column chromatography on a Biotage SP1 system (DCM/EtOAc; v/v 1:1) to give the title compound as a clear oil (0.160 g, 19%); 1H-NMR (500 MHz, CDCl3): δ 1.46 (s, 9H, C(CH3)3), 2.47 (br t, J=4.2 Hz, 4H, piperazine N(CH2)2), 3.46 (br t, J=4.5 Hz, 4H, piperazine N(CH2)2), 3.75 (s, 2H, NCH2), 7.20 (s, 1H, thiazole 5-H), 8.79 (s, 1H, thiazole 2-H); LC (Method B)-MS (ESI, m/z): Rt=1.80 min—284 [(M+H)+, 100%].
Loading…
