1,1'-Carbonyldiimidazole → HCID 11385667, compound

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Reaction Steps

4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and CDI were dissolved in anhydrous THF/DMF (5:1) and treated with 3-amino-1,2-propandiol as for example 34. After workup, the residue was further purified by flash chromatography on silica gel (5% MeOH/CH2Cl2—10% MeOH/CH2Cl2 gradient elution) to give N-(2,3-dihydroxypropyl)-4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (33%) as a pale cream solid; m.p. (EtOAc/Hexane) 96-101° C. (glue-liquid). 1H NMR [400 MHz, CH3OD] δ 8.17 (s, 1H), 7.61 (dd, J=9.9, 1.9 Hz, 1H), 7.59-7.55 (m, 1H), 7.22 (t, J=8.4, 1H), 5.78 (s, 1H), 3.85-3.79 (m, 1H), 3.56 (dd, J=5.4, 2.3 Hz, 2H), 3.51 (s, 3H), 3.53-3.50 (m, 1H), 3.39-3.33 (m, 1H). HRMS (FAB+) calcd for C16H18FIN3O4 462.0326 (M+), found 462.0332. HPLC 84.8% (254 nm).

Provenance & Evidence