5-Aminoisoquinoline → 1-Cyclopentyl-3-(isoquinolin-5-yl)urea
Reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.CCN(C(C)C)C(C)C.[N:21]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[C:22]=[O:23]>C(Cl)Cl>[CH:24]1([NH:21][C:22]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][N:2]=[CH:1]3)=[O:23])[CH2:28][CH2:27][CH2:26][CH2:25]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To isoquinolin-5-amine (0.23 g, 1.595 mmol) in DCM (5 mL) was added DIEA (0.557 mL, 3.19 mmol) and isocyanatocyclopentane (0.180 mL, 1.595 mmol). After 24 h, the reaction was quenched with H2O (15 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (10 mL) and dried (MgSO4). The impure yellow solid was collected and was carried onto the next step. MS (ESI) m/z: 256 (M+H)+.