Trifluoroacetic acid → 3-n-Butyl-1-[2-chloro-5-(propionylamino)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile

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A mixture of 142 mg (0.218 mmol) of 3-n-butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-1-[2-chloro-5-(propionylamino)phenyl]-1H-pyrazole-5-carbonitrile (from Step J), 237 μL (236 mg, 2.18 mmol) of anisole, and 675 μL of trifluoroacetic acid (TFA) was stirred at room temperature overnight in a stoppered flask. The mixture was evaporated under a stream of N2, and the residue was flash chromatographed on silica gel (elution with 1% and then 3% MeOH in CH2Cl2), yielding 126 mg (97%) of the title compound as a slightly yellow, stiff foam; nearly homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 594 (M+1)+. 400 MHz 1H NMR (CDCl3) δ0.93 (t, J=7.3 Hz, 3H), 1.20 (t, J=7.5 Hz, 3H), 1.40 (m, 2H), 1.67 (m, 2H), 2.37 (q, J=7.5 Hz, 2H), 2.69 (t, J=7.8 Hz, 2H), 4.02 (s, 2H), 4.52 (s, 2H), 7.2-7.6 (m, 8H), 7.81 (d, J=2.5 Hz, 1H), 8.15 (dd, J=8.0, 1.3 Hz, 1H).

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