Diisopropylethylamine → HCID 59553069, compound

Participants

Reaction Steps

3-Fluoro-5-cyclohexyloxybenzoic acid (100 mg, 420 μmol), 4-amino-1-(2-morpholinoethoxy)naphthalene (103 mg, 378 μmol), HBTU (238 mg, 630 μmol), DIPEA (220 μl, 1.26 mmol), and DMF (1.5 ml) are stirred for 12 hours at room temperature. CH2Cl2 (2 ml) is added to the mixture, and it is then washed with H2O, NaHCO3 solution, and brine. The organic layer is dried over Na2SO4 and concentrated. The residue is purified by column chromatography on silica gel eluting with ethyl acetate to provide 3-(cyclohexyloxy)-5-fluoro-N-[4-(2-morpholin-4-ylethoxy)-1-naphthyl]benzamide as a brown solid (50 mg). Mp: 116-118° C.; 1H NMR (DMSO-d6) δ 10.29 (s, 1H), 8.21 (m, 1H), 7.87 (m, 1H), 7.57 (m, 2H), 7.52 (s, 1H), 7.42 (m, 2H), 7.07 (m, 2H), 4.51 (m, 1H), 4.31 (t, 2H), 3.61 (t, 4H), 2.89 (m, 2H), 2.62 (t, 4H), 1.93 (m, 2H), 1.72 (m, 2H), 1.46 (m, 6H); MS 493.32 (M+1).

Provenance & Evidence