1,4-Dioxane → HCID 56932574, compound

Participants

Reaction Steps

A solution of tert-butyl 3-(5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)prop-2-ynylcarbamate (698 mg, 1.11 mmol, Example 158) in 4 M HCl in dioxane (10 mL, 40 mmol) was stirred at room temperature for 30 min and then the solvent was removed under reduced pressure. The crude material was subjected to reverse-phase preparative HPLC using a Phenomenex Gemini C18 column (150×30 mm, 10 μm) eluting with 0.1% TFA in CH3CN/H2O (10% to 100% over 15 min) to 2-(3-(3-amino-1-propyn-1-yl)-4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol trifluoroacetate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.77 (s, 1H), 8.24 (br s, 3H), 8.10 (d, J=4.89 Hz, 1H), 7.70 (d, J=3.33 Hz, 1H), 7.56-7.64 (m, 2H), 7.32 (t, J=4.40 Hz, 1H), 7.14 (d, J=8.61 Hz, 1H), 4.01 (s, 2H), 3.27-3.33 (m, 4H), 3.10-3.20 (m, 4H); m/z (ESI, +ve ion) 528.1 (M+H)+. GK-GKRP IC50 (Binding)=1.919 μM.

Provenance & Evidence