To a stirring solution of 1-(4-fluorobenzyl)-3-{[2-(2-oxopyrrolidin-1-yl)ethoxy]methyl}-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (0.817 g, 1.99 mmol) and 2-chloro-4,6-dimethoxy-1,3,5-triazine (0.418 g, 2.38 mmol) in DMF (20 mL) was added N-methyl morpholine (0.2409, 2.38 mmol). After stirring at room temperature for 2 hours, N-methyl hydroxylamine hydrochloride (1.66 g, 19.9 mmol) was added. The reaction stirred for 16 hours at room temperature. After stirring for 16 hours, the reaction was concentrated in vacuo yielding a yellow oil. The oily residue was partitioned between a saturated sodium bicarbonate solution and ethyl acetate (50:50, 50 mL: 50 mL). The organic phase was separated and the aqueous phase extracted with ethyl acetate (2×100 mL). The organic phases were combined, washed with brine (100 mL), and dried over Na2SO4. The solution was filtered, concentrated, and triturated with diethyl ether to yield a pale yellow solid. The solid was recrystalized from isopropyl alcohol to give 1-(4-fluorobenzyl)-N-hydroxy-N-methyl-3-{[2-(2-oxopyrrolidin-1-yl)ethoxy]methyl}-1H-pyrrolo[2,3-c]pyridine-5-carboxamide as clear needles (0.425 g, 49% yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.76-1.85 (m, 2H) 2.13 (t, J=8.08 Hz, 2H) 3.26-3.35 (m, 8H) 3.51 (t, J=5.43 Hz, 2H) 4.65 (s, 2H) 5.54 (s, 2H) 7.16 (t, J=8.84 Hz, 2H) 7.36 (dd, J=8.59, 5.56 Hz, 2H) 7.86 (s, 1H) 8.01 (s, 1H) 8.89 (s, 1H)
