[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.CN1CCNCC1.N1C=CN=C1.C([O:20][C:21]([C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[C:27]([CH3:32])[CH:26]=2)=[O:22])C.C(CNC([C@@H]1CCCC[C@@H]1NC(C1NC2C(C=1)=CC=C(CN1C=CC=N1)C=2)=O)=O)#N.C(CNC([C@@H]1CCCC[C@@H]1NC(C1NC2C(C=1)=CC=C(CN1CCN(C)CC1)C=2)=O)=O)#N>>[N:1]1([CH2:32][C:27]2[CH:26]=[C:25]3[C:30]([CH:31]=[C:23]([C:21]([OH:22])=[O:20])[NH:24]3)=[CH:29][CH:28]=2)[CH:5]=[CH:4][CH:3]=[N:2]1Similarly, using pyrazole and 1-methyl-piperazine respectively in place of imidazole in reaction with 6-methyl-1H-indole-2-carboxylic acid ethyl ester, the compounds 6-pyrazol-1-ylmethyl-1H-indole-2-carboxylic acid and 6-(4-methyl-piperazin)-1-ylmethyl-1H-indole-2-carboxylic acid were prepared. These acids in turn were used to make 6-pyrazol-1-ylmethyl-1H-indole-2-carboxylic acid [(1S,2R)-2-(cyanomethyl-carbamoyl)-cyclohexyl]-amide and 6-(4-methyl-piperazin-1-ylmethyl)-1H-indole-2-carboxylic acid [(1S,2R)-2-(cyanomethyl-carbamoyl)-cyclohexyl]-amide using the coupling procedure of Example 10.
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