DIPEA (45 mg, 0.35 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (26 mg, 0.1 mmol) in DMF (1 mL) followed by HOBt (20 mg, 0.15 mmol) and EDCI.HCl (28 mg, 0.15 mmol). After 2 minutes of stirring, 2-amino-1-[4-(5-bromo-2-methoxy-phenylamino)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 2 and 5 of the General Scheme) (0.03 g, 0.0001 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure Purification by column chromatography (using neutral alumina and 5% MeOH in CHCl3 as eluent) to afford 60 mg (35% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(5-bromo-2-methoxy-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 512.4, 91%, 1H NMR (300 MHz, DMSO-d6): δ10.2 (m, 1H), 7.9 (m, 1H), 7.7 (m, 7H), 7.4 (m, 2H), 7.2 (m, 1H), 3.6 (m, 5H), 2.0 (m, 2H), 1.8 (m, 2H).
