[CH3:1][C:2]([CH3:18])([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:8]1)=[O:6])[CH3:3].Cl[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O.O.C(Cl)Cl>[CH3:3][C:2]([CH3:18])([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:14][CH2:15][CH2:16][CH3:17])[C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:1]
A mixture of 1-(1,1-dimethylethoxycarbonyl)-4-(butylamino)piperidine (VIII, EXAMPLE 86, 1.30 g), 2-chloro-3-nitropyridine (804 mg) and diisopropylethylamine (1.77 ml) in N-methyl-2-pyrrolidinone (15 ml) is stirred at 85° for 24 hrs, diluted with water (75 ml) and methylene chloride (150 ml), and the layers are separated. The aqueous phase is extracted with methylene chloride (2×25 ml) and the combined organic phase is washed with saline (25 ml), dried over sodium sulfate, and concentrated under reduced pressure at approximately 75°. The residue is chromatographed on silica gel (230-400 mesh, 100 g; eluting with ethyl acetate/hexane (5/95)) to give the title compound, NMR (CDCl3) 8.33, 8.05, 6.73, 4.20, 3.82, 3.30, 2.73, 1.84-1.71, 1.47, 1.40-1.20 and 0.86δ.
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