Tetrabutylammonium Fluoride → 6-(7-(4-(3-cyclopropylureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-N-methyl-N-((2R,3S,4S,5S)-2,3,4,5,6-pentahydroxyhexyl)nicotinamide

Participants

Reaction Steps

To a solution of 243 (250 mg, 0.228 mmol) in THF (5 mL) was added TBAF (1.0M in THF) (0.273 mL, 0.273 mmol) and the reaction mixture was stirred for 2 hr at RT before concentration. The residue was purified by Biotage, (MeOH/DCM, 20-50%, SNAP 25 g cartridge) and Gilson (Phenomenex, Luna, 15μ, C18(2) 100A, 250×50.00 mm, 15 μm, 0.05% of formic acid in both MeOH/H2O, 40-90%, flow=30 mL/min), to afford title compound 244 (10 mg, 0.016 mmol, 7% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.72 (d, 1H, J=3.9 Hz), 8.47 (s, br, 1H), 8.19-8.13 (m, 2H), 8.13-8.00 (m, 1H), 7.65 (dd, 1H, J1=2.5 Hz, J2=13.1 Hz), 7.29 (t, 1H, J=8.81 Hz), 7.20-7.17 (m, 1H), 6.64 (d, 1H, J=5.3 Hz), 4.20-4.18 (m, 0.45H), 4.07-4.04 (m, 0.55H), 3.83-3.53 (m, 7H), 3.17 (s, 3H), 2.62-2.57 (m, 1H), 0.78-0.73 (m, 2H), 0.54-0.50 (m, 2H). MS: 642.6 (MH+).

Provenance & Evidence