3-Methoxypropyne → HCID 86670379, 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 methyl propargyl ether (Aldrich, St. Louis, Mo.) to afford 1,1,1,3,3,3-hexafluoro-2-(3-(3-methoxyprop-1-ynyl)-4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)propan-2-ol. 1H NMR (400 MHz, DMSO-d6) δ 8.71 (s, 1H), 8.10 (dd, J=1.00, 4.90 Hz, 1H), 7.69 (dd, J=0.88, 3.62 Hz, 1H), 7.54-7.60 (m, 2H), 7.33 (dd, J=4.01, 4.79 Hz, 1H), 7.12 (d, J=8.80 Hz, 1H), 4.30 (s, 2H), 3.27-3.30 (m, J=5.10 Hz, 4H), 3.23 (s, 3H), 3.10 (d, J=4.30 Hz, 4H); m/z (ESI, +ve ion) 543.2 (M+H)+. GK-GKRP IC50 (Binding)=0.363 μM. GK-GKRP EC50 (LC MS/MS-2)=0.675 μM.

Provenance & Evidence