N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-5-({3-[(1,1-dimethylethyl)oxy]propanoyl}amino)-1H-indole-2-carboxamide → N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-5-[(3-hydroxypropanoyl)amino]-1H-indole-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-5-({3-[(1,1-dimethylethyl)oxy]propanoyl}amino)-1H-indole-2-carboxamide (0.040 g, 0.067 mmol) was dissolved in 4N HCl in dioxane (3 mL). The solution was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and the solvent was evaporated. The residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA) to give the title compound (0.007 g, 19%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.49 (br. s., 1H), 9.70 (s, 1H), 8.67-9.07 (m, 1H), 7.95 (s, 1H), 7.77 (s, 1H), 7.42-7.53 (m, 2H), 7.37 (d, 1H), 7.25-7.32 (m, 1H), 7.19-7.25 (m, 1H), 7.06 (s, 1H), 4.52 (d, 2H), 3.62-3.73 (m, 2H), 3.51-3.60 (m, 1H), 2.40 (t, 2H). ES MS: m/z 541 (M+1).

Provenance & Evidence