Phosgene → 1-[5-Tert-butyl-3-methylcarbamoyl-2-methoxyphenyl]-3-[4-(4-pyridinyloxy)-naphthalen-1-yl]-urea

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Reaction Conditions

Reaction Steps

1-Amino-4-(4-pyridinyloxy)naphthalene (Example 6) (1.0 mmol) is dissolved in dichloromethane (15 mL). An equal volume of sat. aqueous sodium bicarbonate is added, and the biphasic solution is cooled to 0° C. During the addition of phosgene (1.93 M in toluene, 1.0 mL), stirring is stopped. Immediately afterward, stirring is resumed for 15 min with the reaction mixture at 0° C. The layers are separated, the organics dried over solid magnesium sulfate and concentrated to approximately 5 mL of solution. 5-tert-Butyl-3-methylcarbamoyl-2-methoxyaniline (Example 3) (0.9 mmol) in dichloromethane (5 mL) is added, and the reaction mixture is stirred overnight at ambient temperature. The solvent is removed by rotary evaporation and the resulting product purified by flash chromatography over silica gel with a suitable elutant such as CH2Cl2:MeOH (95:5) to give the title compound.

Provenance & Evidence