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Example 89 N-(1,3-Dioxo-2,3-dihydro-1H-5-isoindolyl)-N’-(2,3,6-trichlorobenzyl)urea Diphenylphosphoryl azide (162 mg, 0.59 mmol, 1.2 eq) and triethylamine (60 mg, 0.59 mmol, 1.2 eq) were added to a solution of 2,3,6-trichlorophenylacetic acid (118 mg, 0.49 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (80 mg, 0.49 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2.5 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate to give the title compound as a crystal (57 mg, 29.1%). MS m/z: 397, 399 1H-NMR delta: 4.63 – 4.66 (2H, m), 6.87 (1H, t, J = 5.24 Hz), 7.55 (1H, d, J = 8.54 Hz), 7.57 (1H, dd, J = 1.95, 8.05 Hz), 7.67 (2H, d, J = 8.54 Hz), 8.00 (1H, d, J = 1.71 Hz), 9.14 (1H, s), 11.09 (1H, s)
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Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem