HCID 11255499, compound → HCID 11449997, compound

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4-[2-Fluoro-4-(3-hydroxy-1-propynyl)anilino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide was hydrogenated in MeOH/THF in the presence of 5% Pd/C as for example 3. Purification of the crude oil was carried out by column chromatography on silica gel (5% MeOH/CH2Cl2 as eluant) to give 4-[2-fluoro-4-(3-hydroxypropyl)anilino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a crystalline cream solid (90%), m.p. (EtOAc/MeOH) 214-216° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.15 (s, 1H), 8.32 (s, 1H), 7.85 (br s, 1H), 7.43 (br s, 1H), 7.33 (t, J=8.3 Hz, 1H), 7.17 (dd, J=11.8, 1.7 Hz, 1H), 7.07 (dd, J=8.2, 1.6 Hz, 1H), 5.40 (s, 1H), 4.50 (t, J=5.1 Hz, 1H), 3.41 (q, J=6.0 Hz, 2H), 3.36 (s, 3H), 2.63 (t, J=7.7 Hz, 2H), 1.76-1.69 (m, 2H). Anal. Calcd for C16H18FN3O3: C, 60.2; H, 5.7; N, 13.2. Found: C, 60.5; H, 5.8; N, 13.3.

Provenance & Evidence