[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8].Cl.Cl[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]Cl>C1(C)C(C)=CC=CC=1>[Cl:22][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]3)[CH2:20]1)[CH2:18]2)=[O:8]To a solution of 5-amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (1.00 g, Example 4b) in xylene (20 ml) was added bis-(2-chloroethyl)amine hydrochloride salt (0.620 g). The mixture was heated at 150° C. for 12 h (a dark solution is obtained). The cold solution was washed with 2M HCl, the aqueous layer washed with ethyl acetate then basified with sodium bicarbonate and extracted twice with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to give a foam. The crude material was purified on silica gel (0-10% ethanol/dichloromethane), to afford the title compound as a white solid (0.90 g).
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