[F:1][C:2]([F:16])([C:12]([F:15])([F:14])[F:13])[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.CN(C)C=O.Cl[CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[C:41]3[C:36](=[CH:37][C:38]([O:42][CH2:43][O:44][CH3:45])=[CH:39][CH:40]=3)[S:35][CH2:34][C:33]2([C:47]2[CH:52]=[CH:51][C:50]([O:53][CH2:54][O:55][CH3:56])=[CH:49][CH:48]=2)[CH3:46])=[CH:28][CH:27]=1>O>[CH3:45][O:44][CH2:43][O:42][C:38]1[CH:37]=[C:36]2[C:41]([CH:32]([C:29]3[CH:28]=[CH:27][C:26]([O:25][CH2:24][CH2:23][N:9]4[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:16])[C:12]([F:13])([F:14])[F:15])[CH2:11][CH2:10]4)=[CH:31][CH:30]=3)[C:33]([C:47]3[CH:52]=[CH:51][C:50]([O:53][CH2:54][O:55][CH3:56])=[CH:49][CH:48]=3)([CH3:46])[CH2:34][S:35]2)=[CH:40][CH:39]=1Under argon atmosphere 4-(4,4,5,5,5-pentafluoropentyl)piperazine (70 mg, 0.4 mmol) was added to dimethylformamide solution (0.5 ml) of (3RS,4RS)-4-[4-(2-chloroethyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-thiochroman (69 mg, 0.13 mmol) and then stirred for 8 hours at 80° C. After adding water, the reaction solution was extracted with ethyl acetate. The extract was distilled under reduced pressure to remove the solvent and the crude product thus obtained was then purified using amino silica gel plate (ethyl acetate:hexane=1:2) to obtain 67 mg (yield: 77%) of the title compound.
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