Water → N-[3-(dimethylamino)propyl]-5-iodo-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Participants

Reaction Steps

To a suspension of 5-iodo-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid (10 g, 23.64 mmol) in DMF (20 mL) was added a solution of carbonyldiimidazole (5.14 g, 30.72 mmol) in DMF (30 mL) over a period of 40 min at 25° C. After stirring the mixture for 30 minutes, was added a solution of N,N-dimethylpropane-1,3-diamine (3.62 g, 35.45 mmol) in DMF (10 mL) over a period of 20 min at 25° C. and stirred for 40 minutes. After completion of the reaction, water (100 mL) was charged at 25° C. over a period of 1 h. The resulting suspension was stirred for 4 h and filtered. The cake was washed with water (50 mL) and dried under vacuum at 50° C. for 12 h to afford the title product as a light brown solid (10 g, 83%); 1H NMR (400 MHz, CDCl3) δ 9.36 (bs, 1 H), 8.87 (s, 1 H), 7.82 (d, J=7.53 Hz, 1 H), 7.76 (t, J=7.78Hz, 1 H), 7.49 (s, 1 H), 7.41 (d, J=8.03 Hz, 1 H), 3.43 (q, J=6.86 Hz, 2 H), 2.30-2.35 (m, 2 H), 2.29 (s, 3 H), 2.20 (s, 6 H), 1.74 (p, J=7.28 Hz, 2 H); LCMSm/z: 508 [M+].

Provenance & Evidence