[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](O)=[O:18].O.ON1C2C=CC=CC=2N=N1.Cl.C(N(CC)CCCN=C=NCC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][NH:8][C:17]([C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)=[O:18])[CH:9]=[CH:10][CH:11]=1A mixture of 3-methoxyphenethylamine (1.000 g, 6.61 mmol), 2-thiophenecarboxylic acid (0.847 g, 6.61 mmol), 1-hydroxybenzotriazole hydrate (1.340 g, 9.92 mmol), and 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.330 g, 6.94 mmol) in anhydrous CH2Cl2 (20 ml) was stirred at 0° C. under N2 for 1 hr, then warmed to rt and stirred at rt for 18 hr. The reaction mixture was washed with 1M NaOH (10 ml) followed by 1M HCl (10 ml), dried over MgSO4, and concentrated in vacuo to give 1.859 g of yellow oil. Purification by flash chromatography, eluting with hexane:EtOAc (7:3) gave 1.637 g (95% yield) of yellow oil.
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