N1(C2C=CC([C:13]3[CH:14]=[CH:15][C:16]4[O:22][CH2:21][CH2:20][C:19]([C:23](O)=[O:24])=[CH:18][C:17]=4[CH:26]=3)=CC=2)CCCCC1.C[N:28](CC1C=CC(N)=CC=1)C1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[O:22]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:26][C:17]=2[CH:18]=[C:19]([C:23]([NH2:28])=[O:24])[CH2:20][CH2:21]1To a solution of 7—(4-piperidinophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (0.15 g), 4—(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)aniline (0.1 g) and 1-hydroxy-benzotriazole (0.07 g) in dimethylformamide (10 ml) was added 1-ethyl-3—(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.13 g) under ice-cooling. Under nitrogen atmosphere, the mixture was warmed to room temperature. To the mixture were added 4-dimethylaminopyridine (catalytic amount) and triethylamine (0.18 ml), and the mixture was stirred over night. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 7—(4-piperidinophenyl)-N-(4—((N-methyl-N-tetrahydro-pyran-4-yl)amino)methyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 151) (0.18 g) as colorless crystals.
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