N,N-二异丙基乙胺 → 3-tert-butoxy-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-benzamide

To a solution of 3-tert-butoxy-benzoic acid (0.15 g, 0.774 mmol) in dimethylformamide (5 ml) is added HBTU (0.44 g, 1.5 eq) followed by the addition of diisopropylethylamine (0.296 ml, 3.0 eq). The mixture is stirred at room temperature for five minutes. A solution of 4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-ylamine (0.21 g) in dimethylformamide (2 ml) is then added. This mixture is stirred at room temperature for 15 h, diluted with water and extracted with ethyl acetate. The organic layer is washed with water, dried over Na2SO4 and evaporated. The residue is purified by column chromatography on silica gel (ethyl acetate) to give 3-tert-butoxy-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-benzamide (0.146 g). Mp: 50-51° C. 1H NMR (300 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.22 (m, 1H), 7.85 (m, 2H), 7.66 (s, 1H), 7.55 (m, 2H), 7.23 (d, J=7.5 Hz, 1H), 7.03 (d, J=8.1 Hz, 1H), 4.31 (t, J=5.1 Hz, 2H), 3.61 (t, J=4.2 Hz, 4H), 2.89 (brs, 2H), 2.58 (brs, 4H), 1.35 (s, 9H). MS: 449 (M+1).

1. stirringThis mixture is stirred at room temperature for 15 h
2. extractionextracted with ethyl acetate
3. washThe organic layer is washed with water
4. dry with materialdried over Na2SO4
5. customevaporated
6. customThe residue is purified by column chromatography on silica gel (ethyl acetate)

ORD记录

ord-52c4335aff1740cda27500e990a76fd4

来源数据集

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

专利号

US08114873B2