Diisopropylamine → HCID 59553173, compound

Participants

Reaction Steps

To a solution of [4-(2-morpholin-4-ylethoxy)-1-naphthyl]amine (0.60 g, 2.2 mmol) in DMF (2 ml) is added 3-fluoro-5-(4-methylpiperidin-1-yl)benzoic acid (0.63 g, 2.64 mmol), prepared from 4-methylpiperidine according to conditions described in general procedure E, HBTU (1.25 g, 3.3 mmol) and diisopropylamine (1.15 ml, 6.6 mmol). This mixture is stirred at room temperature overnight and diluted with CH2Cl2 (5 ml), washed with 0.05 N NaOH, dried over Na2SO4 and concentrated. The residue is purified by column chromatography on silica gel (90% EtOAc in hexane) to give 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2-morpholin-4-ylethoxy)-1-naphthyl]benzamide as a white solid (0.53 g). Mp: 116-118° C.; 1H NMR (300 MHz, DMSO-d6) δ 0.91(d, 6.3 Hz, 3H), 1.15-1.25(m, 2H), 1.67(d, J=12 Hz, 2H), 2.55(bs, 4H), 2.74(t, J=12.3 Hz, 2H), 2.86(s, 2H), 3.59(t, J=4.5 Hz, 4H), 3.82(d, J=12.9 Hz, 2H), 4.29(t, J=5.7 Hz, 2H), 6.93(d, J=12.6 Hz, 1H), 7.00(d, J=8.1 Hz, 1H), 7.12(d, J=8.7 Hz, 1H), 7.37-7.43(m, 2H), 7.51-7.55(m, 2H), 7.81-7.84 (m, 1H), 8.17-8.20(m, 1H), 10.21 (s, 1H); MS 492 (M+1).

Provenance & Evidence