Dichloromethane → 3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-6-sulfonamide

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Reaction Steps

A vial was charged with N-(2,4-dimethoxybenzyl)-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-6-sulfonamide (Intermediate J) (46.47 mg, 0.071 mmol) and DCM (0.5 mL) to give a clear solution. TFA (0.1 mL) was added dropwise, and the resulting mixture was stirred for 30 min. The mixture was diluted with methanol, then filtered through Celite® (diatomaceous earth). The filtrate was concentrated, and the residue was triturated with diethyl ether to give a white solid. The diethyl ether was decanted, and the solid was put under vacuum again for 10 min. Diethyl ether was added, and the suspension was sonicated for 1 min to give a fine white precipitate. The mixture was filtered on a membrane filter, and the collected solid was washed with diethyl ether (3×), then dried under a stream of N2 to give 3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-6-sulfonamide (18.02 mg, 0.036 mmol, 50.3% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.49 (d, J=2.4 Hz, 1 H), 8.45 (s, 1 H), 8.01 (s, 1 H), 7.94-7.88 (m, 2 H), 7.79 (s, 1 H), 7.65 (d, J=8.3 Hz, 1 H), 7.40 (s, 1 H), 7.35 (d, J=2.7 Hz, 1 H), 6.37 (d, J=1.9 Hz, 1 H), 3.23 (s, 3 H). m/z (ESI) 506.0 (M+H)+.

Provenance & Evidence