Tris(hydroxymethyl)aminomethane → HCID 11191054, compound

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4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and CDI were dissolved in anhydrous THF/DMF (4:1) and treated with 2-amino-2-[hydroxymethyl]-1,3-propandiol as for example 34. After the standard workup, trituration with hexane gave 4-(2-fluoro-4-iodoanilino)-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (22%) as a yellow/cream solid; m.p. (EtOAc/Hexane) 100-105° C. (glue-liquid). 1H NMR [400 MHz, (CD3)2SO] δ 9.62 (br s, 1H), 8.15 (s, 1H), 7.73 (dd, J=10.2, 1.7 Hz, 1H), 7.57 (d, J=8.5 Hz, 1H), 7.32 (s, 1H), 7.26 (t, J=8.5 Hz, 1H), 5.54 (s, 1H), 4.59 (t, J=5.7 Hz, 3H), 3.68 (d, J=5.7 Hz, 6H), 3.37 (s, 3H). HPLC 78.1% (254 nm). HRMS (FAB+) cald for C17H20FIN3O5 492.043 (M+), found 492.0425.

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