[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Cl:25][CH2:26][C:27]([NH:29][C:30]1[CH:31]=[N:32][C:33]([CH3:36])=[CH:34][CH:35]=1)=[O:28]>C(#N)C.C(OCC)(=O)C.CCCC(C)C>[Cl-:25].[CH3:36][C:33]1[N:32]=[CH:31][C:30]([NH:29][C:27]([CH2:26][N+:1]23[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:28])=[CH:35][CH:34]=11-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 1e)(52 mg) was dissolved in acetonitrile (2 mL) and 2-chloro-N-(6-methylpyridin-3-yl)acetamide (Example f) (29 mg) was added. The reaction mixture was stirred for 10 days and diluted with ethyl acetate (4 mL) and isohexane (14 mL). The mixture was left standing for 5 days, whereupon the resulting crystals were separated and washed with diethyl ether (0.5 mL) to afford the titled compound as a solid (36 mg).
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