[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:4]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:23])[C:20](O)=[O:21])=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH:9][C:20](=[O:21])[CH:19]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH3:23])=[CH:5][CH:4]=1To a stirred mixture of p-methoxyphenethyl amine (3.28 g, 21.7 mmol), p-fluorophenyl propionic acid (3.31 g, 19.7 mmol), and 150 ml anhydrous dichloromethane was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (4.16 g, 21.7 mmol). The mixture was stirred at ambient temperature for 40 hours and then washed with 1N sodium hydroxide, 1N hydrochloric acid, and saturated sodium chloride, dried, filtered and evaporated to a green solid (5.41 g, 91%). 1H NMR (CDCl3) δ 7.18 (m, 2H); 6.98 (m, 4 H); 6.81 (d, 2 H); 5.32 (br s, 1 H); 3.79 (s, 3 H); 3.44 (q, 2 H); 2.90 (t, 2 H); 2.68 (t, 2 H); 2.39 (t, 2 H).
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