Benzoic Acid → HCID 18351492, compound

Participants

Reaction Steps

A solution of (E)-3-(3-aminopropenyl)-4-(2-methoxy-ethoxymethoxy)benzonitrile (0.12 g, 0.46 mmol) in DMF is treated with 6methoxy-pyridin-3-yl)-benzoic acid, TBTU and Et3N as described in EXAMPLE 309, part B. Standard workup and chromatography gives the desired 3-{3-[4-(6-oxo-1,6-dihydro-pyridin-3-yl)benzamido]propyl}-4-(2-methoxyethoxy-methoxy)-benzonitrile (0.22 g, 0.46 mmol). A portion of the benzonitrile (0.09 g, 0.19 mmol) is converted to the benzamidine by treatment with anhydrous HCl/EtOH followed by ammonolysis as described in EXAMPLE 307, part D. The product is purified by HPLC eluting with a gradient of 10% MeCN/H20 (0.1% TFA) to 100% MeCN to give title compound as a white solid (0.05 g, 0.12 mmol). 1H NMR (CD3OD, 300 MHz) δ8.43 (d, 1H), 7.95 (m, 4H), 7.70 (d, 2H), 7.55 (dd, 1H), 6.90 (m, 3H), 6.53 (m, 1H), 4.18 (d, 2H), 3.95 (s, 3H). Ion spray MS [M+1]+=403.

Provenance & Evidence