[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.[CH2:22]([O:24][C:25](=[O:53])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][CH2:36][NH:37][CH2:38][CH2:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:29]=1)[CH3:23].Cl>CN(C=O)C.CCOC(C)=O>[CH2:22]([O:24][C:25](=[O:53])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][CH2:36][N:37]([CH2:38][CH2:39][CH:40]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:9](=[O:11])/[CH:8]=[CH:7]/[C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH:29]=1)[CH3:23]To a solution of (2E)-3-(4-pyridinyl)acrylic acid (23 mg) in DMF (1 mL) was added HOBt (21 mg), ethyl(3-{3-[(3,3-diphenylpropyl)amino]propyl}phenoxy)acetate (55 mg) and WSCD.HCl (29 mg) at ambient temperature. The reaction mixture was stirred for 8 hours at the same temperature. The resulting mixture was diluted with EtOAc and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=85:15-70:30) to give a ethyl[3-(3-{(3,3-diphenylpropyl) [(2E)-3-(4-pyridinyl)-2-propenoyl]amino}propyl)phenoxy]acetate.
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