Ammonium Hydroxide → Tert-butyl 4-(1-(2-aminonicotinoyl)isoquinolin-3-yl)piperazine-carboxylate
Reaction equation
F[C:2]1[N:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[N:7]=1)=[O:5].[OH-].[NH4+:34]>>[NH2:34][C:2]1[N:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[N:7]=1)=[O:5]Participants
3
Conditions
- Temperature
- 120 °C
Procedure
A microwave vial was charged with tert-butyl 4-(1-(2-fluoronicotinoyl)isoquinolin-3-yl)piperazine-1-carboxylate (8 mg, 0.018 mmol) and a saturated aqueous solution of ammonium hydroxide (3 ml). The reaction mixture was heated under microwave irradiation at 120° C. for 30 minutes. The mixture was cooled down to room temperature, partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified on silica gel by flash column chromatography to afford the title compound as a yellow solid (6 mg, 76% yield).