Molecules 2021, 26, 2525
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column chromatography to afford compound 11a as a white solid (20 mg, 53%). 1H NMR
(500 MHz, Chloroform-d),
δ 8.95 (d, J = 2.7 Hz, 1H), 8.77 (s, 1H), 8.51 (d, J = 8.3 Hz, 1H),
8.31–8.21 (m, 2H), 7.74–7.64 (m, 2H), 7.53 (dd, J = 8.5, 4.3 Hz, 1H), 7.48 (ddd, J = 20.2, 7.3,
0.7 Hz, 1H), 6.89 –6.76 (m, 4H), 5.29 (s, 1H), 4.94 (ddd, J = 12.5, 6.0, 3.0 Hz, 1H), 4.63–4.42
(m, 2H), 4.24–4.15 (m, 3H), 3.87 (dd, J = 9.1, 7.9 Hz, 1H), 3.68 (s, 1H), 2.96–2.85 (m, 1H),
2.84–2.68 (m, 2H), 2.19–2.11 (m, 1H), 1.53 (s, 3H). 13C NMR (126 MHz, Chloroform-d),
δ
172.68, 170.74, 168.71, 168.17, 166.82, 153.54, 152.71, 152.33, 141.57, 137.82, 136.46, 134.82,
131.39, 129.48, 123.74, 119.43, 118.78, 117.84, 116.17, 116.00, 115.97, 115.91, 115.66, 114.89,
99.00, 75.69, 73.03, 66.75, 64.62, 49.22, 31.36, 22.98, 22.75; HR-MS (EI) calculated for (M+)
781.0881; found 781.0887.
2-(2-(4-(3-((4-Cyano-3-iodophenyl)amino)-2-hydroxy-2-methyl-3-
oxopropoxy)phenoxy)ethoxy)ethyl
(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)carbamate (11b)
Compound 11b was prepared using a similar method for the synthesis of 11a (43%).
1H NMR (500 MHz, Chloroform-d),
δ 8.98 (d, J = 7.6 Hz, 1H), 8.77 (d, J = 14.3 Hz, 1H), 8.51
(d, J = 8.6 Hz, 1H), 8.29 (d, J = 2.1 Hz, 1H), 8.23 (d, J = 14.8 Hz, 1H), 7.74–7.63 (m, 2H), 7.54
(d, J = 8.5 Hz, 1H), 7.45 (ddd, J = 7.3, 2.4, 0.7 Hz, 1H), 6.87 –6.71 (m, 4H), 5.29 (s, 1H), 4.93
(ddd, J = 12.7, 5.5, 3.5 Hz, 1H), 4.45–4.28 (m, 2H), 4.07 (ddd, J = 5.4, 3.9, 2.7 Hz, 2H), 3.84
(dtd, J = 6.0, 4.4, 1.7 Hz, 5H), 2.94–2.85 (m, 1H), 2.83–2.68 (m, 2H), 2.16 (s, 1H), 2.19–2.11
(m, 1H), 1.52 (d, J = 1.5 Hz, 3H). 13C NMR (126 MHz, Chloroform-d)
δ 172.76, 170.81,
168.66, 168.05, 166.83, 153.85, 152.88, 152.00, 141.61, 137.91, 136.37, 134.81, 131.33, 129.50,
123.85, 119.45, 118.80, 117.74, 116.10, 115.95, 115.82, 115.76, 115.65, 114.87, 98.99, 73.45, 73.22,
69.74, 69.30, 68.17, 65.01, 49.21, 31.38, 22.98, 22.70; HR-MS (EI) calculated for (M+) 825.1143;
found 825.1143.
2-(2-(2-(4-(3-((4-Cyano-3-iodophenyl)amino)-2-hydroxy-2-methyl-3-
oxopropoxy)phenoxy)ethoxy)ethoxy)ethyl
(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)carbamate (11c)
Compound 11c was prepared using a similar method for the synthesis of 11a (27%).
1H NMR (500 MHz, Chloroform-d), δ 8.97 (s, 1H), 8.84 (d, J = 5.6 Hz, 1H), 8.53 (d, J = 8.7 Hz,
1H), 8.28 (d, J = 1.8 Hz, 1H), 8.16–8.07 (m, 1H), 7.73–7.64 (m, 2H), 7.54 (dd, J = 8.5, 2.4 Hz,
1H), 7.47 (d, J = 7.4 Hz, 1H), 6.79 (q, J = 9.6 Hz, 4H), 5.29 (s, 1H), 4.85 (ddd, J = 12.5, 5.3,
2.4 Hz, 1H), 4.40–4.31 (m, 3H), 4.07 (dd, J = 5.8, 4.1 Hz, 2H), 3.91–3.82 (m, 3H), 3.78–3.68
(m, 5H), 3.69 (d, J = 3.5 Hz, 1H), 3.65 (d, J = 3.5 Hz, 1H), 2.91–2.84 (m, 1H), 2.82–2.64 (m, 2H),
2.14–2.07 (m, 1H), 1.60 (s, 3H). 13C NMR (126 MHz, Chloroform-d),
δ 172.99, 170.89, 168.73,
168.08, 166.79, 153.96, 152.97, 151.94, 141.61, 137.97, 136.45, 134.85, 131.37, 129.52, 123.83,
119.48, 118.82, 117.86, 115.91, 115.73, 99.02, 75.87, 73.26, 70.88, 70.80, 69.96, 69.15, 68.08,
65.05, 49.24, 31.04, 23.02, 22.65; HR-MS (EI) calculated for (M+) 869.1405; found 869.1403.
5-(4-(3-((4-Cyano-3-iodophenyl)amino)-2-hydroxy-2-methyl-3-
oxopropoxy)phenoxy)pentyl
(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)carbamate (11d)
Compound 11d was prepared using a similar method for the synthesis of 11a (17%).
1H NMR (500 MHz, Chloroform-d), δ 8.95 (d, J = 4.1 Hz, 1H), 8.80 (d, J = 2.7 Hz, 1H), 8.54
(d, J = 8.5 Hz, 1H), 8.27 (dd, J = 2.1, 1.1 Hz, 1H), 8.13 (d, J = 5.9 Hz, 1H), 7.74–7.66 (m, 2H),
7.54 (d, J = 8.5 Hz, 1H), 7.49 (d, J = 7.2 Hz, 1H), 6.80 (m, 4H), 4.93 (dd, J = 12.2, 5.4 Hz,
1H), 4.36 (dd, J = 9.0, 4.0 Hz, 1H), 4.23 (tt, J = 6.6, 3.4 Hz, 1H), 3.94–3.86 (m, 3H), 3.53 (d,
J = 6.6 Hz, 1H), 2.96–2.86 (m, 1H), 2.85–2.69 (m, 2H), 2.19–2.11 (m, 1H), 1.84–1.71 (m, 4H),
1.64–1.56 (m, 2H), 1.57 (m, 3H). 13C NMR (126 MHz, Chloroform-d),
δ 172.76, 170.73, 168.89,
167.91, 166.77, 154.20, 153.14, 151.76, 141.55, 138.15, 136.44, 134.82, 131.34, 129.49, 123.82,
119.43, 118.78, 117.76, 116.05, 116.02, 115.69, 115.57, 115.55, 114.83, 98.99, 75.80, 73.26, 68.17,
65.89, 49.25, 31.40, 28.87, 28.47, 22.99, 22.72, 22.47; HR-MS (EI) calculated for (M+) 823.1350;
found 823.1347.