4-Chlorophenyl Isocyanate → HCID 11634612, compound

Participants

Reaction Steps

To a stirred solution of 3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-dimethylamino-ethoxy)-phenylamine (0.033 g, 0.10 mmol) in CH2Cl2 (2.0 mL) was added 4-chlorophenyl isocyanate (0.017 g, 0.11 mmol, 1.1 equiv.). The solvent was removed after the completion of the reaction and it was purified by the HPLC. The pure fractions were collected and CH3CN was evaporated under vacuum. The residue was diluted with EtOAc and neutralized with saturated NaHCO3, the EtOAc phase was washed with brine, dried over MgSO4, filtered and evaporated. Compound 69 was obtained in 85% yield. LCMS m/z (%)=492 (M+H79Br35Cl, 78), 494 (M+H81Br35Cl, 100), 496 (M+H81Br37Cl, 28). 1H NMR (400 MHz, acetone-d6) δ: 8.27 (s, 1H), 8.20 (1H), 7.66 (dd, J=2.7, 9.0 Hz, 1H), 7.56 (d, J=8.9 Hz, 2H), 7.48 (s, 1H), 7.43 (d, J=2.7 Hz, 1H), 7.29 (d, J=8.9 Hz, 2H), 7.14 (d, J=9.0 Hz, 1H), 3.98-4.20 (m, 2H), 3.73 (s, 1H), 2.48-2.68 (m, 2H), 2.16 (s, 6H).

Provenance & Evidence