tert-butyl N-(prop-2-yn-1-yl)carbamate → HCID 86670382, compound

Participants

Reaction Steps

Following the procedure outlined for Example 152, 2-(3-Bromo-4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (Example 69) was coupled to N-(tert-butoxycarbonyl)propargylamine (Aldrich, St. Louis, Mo.) to afford tert-butyl (3-(2-(4-(2-thiophenylsulfonyl)-1-piperazinyl)-5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-2-propyn-1-yl)carbamate after purification via column chromatography on silica gel (10 to 40% EtOAc in hexanes). 1H NMR (400 MHz, DMSO-d6) δ 8.68 (s, 1H), 8.08 (dd, J=1.00, 5.09 Hz, 1H), 7.69 (dd, J=0.98, 3.72 Hz, 1H), 7.51-7.56 (m, 2H), 7.32 (dd, J=3.91, 4.89 Hz, 2H), 7.07 (d, J=9.39 Hz, 1H), 3.94 (d, J=5.48 Hz, 2H), 3.26-3.29 (m, 4H), 3.12-3.18 (m, 4H), 1.40 (s, 9H); m/z (ESI, +ve ion) 628.1 (M+H)+. GK-GKRP IC50 (Binding)=0.695 μM.

Provenance & Evidence