Trifluoroacetic acid → 4-{4-[3-(6-Piperidin-1-ylmethyl-pyridin-2-yl)-ureido]-thiazol-2-yl)-benzenesulfonamide

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Reaction Steps

To a stirred solution of ethyl 2-(4-sulfamoyl-phenyl)-1,3-thiazole-4-carboxylic acid (90 mg, 0.32 mmol) in dry TFA (3 mL) and 4A molecular sieves at RT and under N2 was added TEA (0.1 mL). After 5 min, (PhO)2PON3 (0.11 mL) and 6-(piperidylmethyl)-2-pyridylamine (0.10 g, 0.51 mmol) were added and the reaction mixture was heated to reflux for 4 h and then cooled to RT. The mixture was washed with 10% HCl (aq) and extracted with EtOAc (3×10 mL). The aqueous layer was brought to a pH 8.0 and extracted with CH2Cl2 (3×20 mL). The extracts were combined, dried over MgSO4, concentrated by rotary evaporation and purified on silica gel (2:1 hexanes/EtOAc and 1:1 MeOH/CH2Cl2) to afford the title compound as a pale yellow solid. EI-MS m/z 473 (M+H). Calc'd for C21H24N6O3S2: 472.14.

Provenance & Evidence