3-Amino-1-propanol → HCID 11371014, compound

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4-(2-Fluoro-4-methylanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and CDI were dissolved in a mixture of anhydrous THF and anhydrous DMF and treated with 3-amino-1-propanol 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) yielding 4-(2-fluoro-4-methylanilino)-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (47%) as a pale cream solid; m.p. (EtOAc/Hexane) 142-145° C. 1H NMR [400 MHz, (CD3)2SO] δ 9.86 (br s, 1H), 8.36 (t, J=5.4 Hz, 1H), 8.21 (s, 1H), 7.30 (t, J=8.4 Hz, 1H), 7.16 (d, J=11.8 Hz, 1H), 7.05 (d, J=7.7 Hz, 1H), 5.40 (s, 1H), 4.48 (t, J=5.1 Hz, 1H), 3.47 (dd, J=11.5, 6.2 Hz, 2H), 3.35 (s, 3H), 3.27 (dd, J=12.8, 6.8 Hz, 2H), 2.32 (s, 3H), 1.67 (p, J=6.7 Hz, 2H). LCMS (ACPI−) 332 (100%). Anal. Calcd for C17H20FN3O3: C, 61.3; H, 6.1; N, 12.6. Found C, 61.0; H, 6.3; N, 12.7.

Provenance & Evidence