Phenyl isocyanate → HCID 59490421, compound

Participants

Reaction Steps

To a solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-ylamine (0.095 g, 0.308 mmol) in dichloromethane (5 mL) was added phenyl isocyanate (37 μL, 0.34 mmol). The reaction mixture was shaken at room temperature for 1 hour. The solvent was removed under reduced pressure and the crude product purified using flash column chromatography (SiO2, gradient from 50% EtOAc in hexane to 66% EtOAc in hexane) to give the desired product, 1-(3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl)-3-phenylurea as a white solid (0.112 g, 84%). Alternative the crude product can be used in the next step without any further purification. M.p. 192-194° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.31 (s, 1H), 8.03 (s, 1H), 7.95 (s, 1H), 7.36 (m, 2H), 7.20 (m, 4H), 6.86 (m, 3H), 6.32 (d, J=7.6 Hz, 1H), 5.54 (s, 2H), 4.05 (m, 1H), 3.70 (s, 3H), 3.17 (m, 1H), 3.08 (m, 3H), 2.81 (m, 1H), 2.11 (m, 1H), 1.89 (m, 1H); LCMS [M+H]: 428.

Provenance & Evidence