Water → HCID 49784700, compound

Participants

Reaction Steps

To a solution of compound 23 (0.080 g, 0.24 mmol) in DCM (10.00 mL) was added 4-dimethylaminopiperidine (0.040 g, 0.31 mmol) and TEA (0.043 g, 0.31 mmol). The reaction was monitored with TLC (25% EtOAc in hexanes, Rf=0.0). The reaction was complete after stirring at room temperature for 30 min, as indicated by the absence of the starting material (TLC). Water was then added and extracted twice with DCM. Combined organic extracts were washed sequentially with water and brine, dried over MgSO4, filtered, and evaporated in vacuo to form a yellow oil. The oil was triturated with DCM and hexanes, and filtered to yield compound 59 as a white powder (0.85 g, 97.4% HPLC purity, 84% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.27 (d, J=2 Hz, 1H), 8.08 (dd, J1=2 Hz, J2=8 Hz, 1H), 7.56 (m, 1H), 7.40 (m, 1H), 7.26 (m, 1H), 7.19 (d, J=9 Hz, 1H), 3.71 (d, J=13 Hz, 2H), 2.77 (t, J=13 Hz, 2H), 2.18 (m, 1H), 2.12 (s, 3H), 1.76 (d, J=11 Hz, 2H), 1.35 (m, 2H); MS (ESI, EI+): m/z=422 (MH+); melting point: 154-157° C.

Provenance & Evidence