[N-:1]=[N+:2]=[N-:3].[Na+].[NH4+].[Cl-].C(OC([N:14]1[CH2:19][CH2:18][CH:17]([O:20][C:21]2[C:22]([C:31]#[N:32])=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)[CH2:16][CH2:15]1)=O)(C)(C)C.ClCCl>CN(C=O)C>[NH:14]1[CH2:19][CH2:18][CH:17]([O:20][C:21]2[C:22]([C:31]3[NH:32][N:3]=[N:2][N:1]=3)=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)[CH2:16][CH2:15]1
Under argon atmosphere 78 mg (1.2 mmol) of NaN3 and 64 mg (1.2 mmol) of NH4Cl were added to a solution of 35 mg (0.1 mmol) 4-(5-Cyano-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (15) in 1 mL of DMF. The mixture was heated to approximately 160° C. and 7 bar pressure for 3 h in a microwave reactor (CEM Discovery). After cooling to room temperature aqueous NH4Cl-solution and dichloromethane was added. The mixture was filtered through a phase separation cartridge and the aqueous layer was washed twice with dichloromethane. The organic layers were combined and the solvents were distilled off. The remainder was subjected to preparative HPLC to yield 4 mg (8%) of compound 32 as trifluoroacetate. LCMS Method # 3, retention time 0.90 min, detected mass 297.04 [M+H]+
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