1,1'-Carbonyldiimidazole → 3,4-Difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamide

Participants

Reaction Steps

The title compound was prepared from reaction of the product of Example 27, Step B, 3,4-difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]benzoic acid with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E. Then, after workup, the crude solid triturated with Et2O and washed with pentane to afford 3,4-difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamide as a white solid (65%); m.p. (Et2O) 129–132° C. 1H NMR [400 MHz, (CD3)2SO] δ 11.80 (br s, 1 H), 8.77 (br s, 1 H), 7.41 (ddd, J=9.0, 5.8, 2.1 Hz, 1 H), 7.23 (dd, J=11.8, 2.1 Hz, 1 H), 7.15 (ddd, J=9.9, 8.9, 7.2 Hz, 1 H), 7.04 (ddd, J=8.5, 2.1, 0.9 Hz, 1 H), 6.85 (ddd, J=9.9, 8.5, 4.2 Hz, 1 H), 4.72 (br s, 1 H), 3.85 (t, J=4.9 Hz, 2 H), 3.57 (t, J=4.9 Hz, 1 H), 2.92 (q, J=7.3 Hz, 2 H), 1.20 (t, J=7.3 Hz, 3 H). Anal. Calcd for C17H17F3N2O3S: C, 52.8; H, 4.4; N, 7.3. Found: C, 53.0; H, 4.7; N, 7.2.

Provenance & Evidence