4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (6-trifluoromethyl-indol-1-yl)-amide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(2-pyridyl)-4-methyl-pyrimidine-5-carboxylic acid (258 mg, 1.2 mmol) and 6-trifluoromethyl-indol-1-ylamine (200 mg, 1 mmol) in DMF (5 mL) is stirred at 50° C. for 0.5 h. The mixture is treated with DMTMM (290 mg, 1.05 mmol) and stirred at 50° C. for 1 h. The mixture is diluted with saturated aqueous Na2CO3 (5 mL) and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is triturated with Et2O/heptane overnight. The precipitate is collected by filtration, washed with H2O (50 mL) and heptane (50 mL), and dried in vacuo to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (6-trifluoromethyl-indol-1-yl)-amide (160 mg, 40%). MS: 398 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 12.13 (s, NH, 1H), 9.36 (s, 1H), 8.82 (d, 1H), 8.48 (d, 1H), 8.04 (m, 1H), 7.83 (m, 3H), 7.60 (m, 1H), 7.44 (d, 1H), 6.74 (d, 1H), 2.80 (s, 3H).

Provenance & Evidence