HCID 49780166, compound → HCID 86686192, compound

Participants

Reaction Steps

Compound 50 (110 mg, 0.21 mmol) was deprotected by stirring overnight with 10% Pd/C in ethanol (15 mL) under a hydrogen atmosphere. The reaction was filtered through a bed of celite and the filtrate evaporated to give intermediate 1-(1-((piperazin-1-yl)acetyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (103 mg, quantitative) as a clear oil, which was used without purification and coupled with acetic acid by Method E. Flash chromatography eluted with 9:1 DCM:MeOH and recrystallization from EtOAc:hexanes afforded compound 51 (73 mg, 74% over 2 steps) as a white solid: Mp 111-122° C. 1H NMR (500 MHz, DMSO-d6) δ 8.52 (s, 1H), 7.47 (d, J=8.9 Hz, 2H), 7.22 (d, J=8.6 Hz, 2H), 6.25 (d, J=7.7 Hz, 1H), 4.15 (d, J=13.1 Hz, 1H), 3.92 (d, J=13.2 Hz, 1H), 3.76-3.67 (m, 1H), 3.47-3.38 (m, 4H), 3.25 (d, J=13.5 Hz, 1H), 3.12 (q, J=13.0 Hz, 2H), 2.81 (t, J=11.5 Hz, 1H), 2.37-2.32 (m, 2H), 1.98 (s, 3H), 2.44-2.40 (m, 2H), 1.90-1.77 (m, 2H), 1.42-1.31 (m, 1H), 1.26-1.15 (m, 1H). Purity 90%. HRMS calculated for C20H21F3N4O3−H+ 470.2015. found (ESI(−), [M−H]) 470.2009.

Provenance & Evidence