Triethylamine → Propanamide, N-(4-((3,5-dimethylphenyl)thio)-1,2-dihydro-5-methyl-2-oxo-3-pyridinyl)-

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Reaction Steps

Freshly distilled propionyl chloride (0.04 ml, 0.41 mmole) (the receptacle is fitted with a trap containing CaCl2) was added to a solution of amine 8a (0.10 g, 0.40 mmole) and triethylamine (0.04 ml, 0.38 mmole) in dichloromethane (5 ml) at 0° C. The mixture was agitated at ambient temperature for 5 hours. The solvent was evaporated, water was added and the solid was isolated by filtration. The residue was purified by column chromatography using a mixture of dichloromethane and ethanol (94:6) as eluant and at the end ethyl acetate in order to obtain the compound 11c (0.10 g, 90%) in the form of a white powder: melting point 186-188° C.; NMR-1H (DMSO-d6) δ 11.86 (1H, s, NH-1), 8.60 (1H, s, NH-3), 7.21 (1H, s, H-6), 6.88 (1H, s, H-4'), 6.80 (2H, s, H-2' and 6'), 4.04 (2H, q, J=7 Hz, COCH2CH3), 2.22 (6H, s, CH3 -3' and 5'), 1.82 (3H, s, CH3 -5), 1.20 (3H, t, J=7 Hz, COCH2CH3). Anal. C17H20N2O2S . 1.25H2O (C, H, N, S).

Provenance & Evidence