2-[4-(3-amino-1-propynyl)-2-fluoroanilino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide → 2-[4-(3-aminopropyl)-2-fluoroanilino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide

Participants

Reaction Steps

The product of Example 9, 2-[4-(3-amino-1-propynyl)-2-fluoroanilino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide was dissolved in absolute EtOH and hydrogenated in the presence of 5% Pd/C by the general procedure of Example 1, Step D. Purification of the resulting oil was carried out by column chromatography on silica gel (1% NH4OH in 25% MeOH/CH2Cl2 as eluant) to give 2-[4-(3-aminopropyl)-2-fluoroanilino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide as a cream solid (46%); m.p. (MeOH/CH2Cl2) 178–181° C. 1H NMR [400 MHz, (CD3)2SO] δ 7.61–7.53 (m, 1 H), 6.97–6.87 (m, 2 H), 6.78 (dd, J=8.2, 1.3 Hz, 1 H), 6.60 (dd, J=15.1, 8.6 Hz, 1 H), 4.10 (br s, 1 H), 3.77 (t, J=5.0 Hz, 2 H), 3.56 (t, J=5.0 Hz, 2 H), 2.70 (t, J=7.3 Hz, 2 H), 2.53 (t, J=8.0 Hz, 2 H), 1.75 (pentet, J=7.5 Hz, 2 H). Not all exchangeable protons observed. Anal. calcd. for C18H20F3N3O3: C, 56.4; H, 5.3; N, 11.0. Await Found.

Provenance & Evidence