Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=1)=[O:5].[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23](Cl)=[O:24])[CH2:19][CH2:18]1)=[O:16].C(N(CC)CC)C>C(#N)C>[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23](=[O:24])[NH:2][CH2:3][C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=2)=[O:5])[CH2:19][CH2:18]1)=[O:16]To a suspension of 2-amino-1-(6-bromopyridin-2-yl)ethanone hydrochloride (10.00 g, 39.8 mmol) obtained in Step 1, trans-4-chlorocarbonylcyclohexanecarboxylic acid methyl ester (9.00 g, 44.0 mmol) in acetonitrile (200 ml), a solution of triethylamine (13.9 ml, 100 mmol) in acetonitrile (60 ml) was added dropwise while ice-cooled for 2 hours. After the reaction solution was concentrated, water was added and extracted with ethyl acetate. The organic layer was sequentially washed with 10% aqueous citric acid, a saturated aqueous sodium bicarbonate, a saturated brine and dried over magnesium sulfate. After concentrated, the residue was purified by flash chromatography on silica gel (n-hexane:ethyl acetate=1:2) and the title compound (7.38 g, 48%) was obtained.
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