Lenvatinib Impurity 14 synthesis

Yield:-

Reaction Conditions:

with methylamine

Steps:

582 4-(3-Chloro-4-(methylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide

Example 582 4-(3-Chloro-4-(methylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide The title compound (65.0 mg, 0.162 mmol, 50%) was obtained as white crystals from phenyl N-(4-(6-carbamoyl-7-methoxy-4-quinolyl)oxy-2-chlorophenyl)carbamate (150 mg, 0.324 mmol) and 40% methylamine (methanol solution), by the same procedure as in Example 11. ¹H-NMR Spectrum (DMSO-d₆) δ (ppm): 2.68 (3H, d, J=4.4 Hz), 4.03 (3H, s), 6.53 (1H, d, J=5.0 Hz), 6.88 (1H, q, J=4.4 Hz), 7.23 (1H, dd, J=2.8, 8.2 Hz), 7.48 (1H, d, J=2.8 Hz), 7.52 (1H, s), 7.74 (1H, s), 7.86 (1H, s), 8.12 (1H, s), 8.25 (1H, d, J=8.2 Hz), 8.67 (1H, s), 8.68 (1H, d, J=5.0 Hz).

References:

US2004/53908,2004,A1