Cl.Cl.[NH2:3][CH:4]1[CH2:12][CH2:11][C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH2:5]1.C[O-].[Na+].CO.C(N(CC)CC)C.[CH:25]1([CH2:31][CH2:32][CH2:33][CH2:34][C:35]([Cl:37])=[O:36])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CC(N(C)C)=O>[ClH:37].[NH:8]1[C:7]2[CH2:11][CH2:12][CH:4]([NH:3][C:35](=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:5][C:6]=2[N:10]=[CH:9]1
To a mixture of 5-amino-4,5,6,7-tetrahydro-1H-benzimidazole, dihydrochloride (420 mg, 2.0 mmol) and DMA (10 ml), 5.4 M NaOMe in MeOH (0.74 ml, 4.0 mmol) was added. triethylamine (0.276 ml, 2 mmol) was added followed by dropwise addition of 5-cyclohexylpentanoic acid chloride (609 mg, 3.0 mmol). When addition was complete the mixture was stirred at ambient temperature for 30 min and then heated at 80° C. for 1 hour and finally allowed to cool to ambient temperature within 1 hour. The volatiles were evaporated and the residue was stirred vigorously with a mixture of H2O (100 ml), 1 N hydrochloric acid (10 ml) and diethyl ether (50 ml). The phases were separated and the aqueous phase was washed with diethyl ether (2×50 ml) and then made alkaline to pH 10-11 with 4 N sodium hydroxide. The alkaline mixture was extracted with ethyl acetate (2×50 ml) and the organic extracts were evaporated in vacuo. The residue was dissolved in 1 N hydrochloric acid and evaporated to dryness. The residue was re-evaporated with acetone to give 260 mg (38%) of the title compound.
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