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7.15 (s, J = 8.7 Hz, 2H); 7.79 (s, J = 12.2 Hz, 1H); 8.54
(d, J = 12.5 Hz, 1H); MS (ESI): 366.1 (C18H18Cl2NO3,
[M+H]+). Anal. Calcd for C18H17Cl2NO3: C, 59.03; H,
4.68; N, 3.82; Found: C, 59.01; H, 4.69; N, 3.85.
J = 13.5 Hz, 1H); MS (ESI): 314.2 (C18H20NO4,
[M+H]+). Anal. Calcd for C18H19NO4: C, 68.99; H,
6.11; N, 4.47; Found: C, 68.98; H, 6.12; N, 4.46.
4.2.14. (Z)-Ethyl 3-(4-bromophenylamino)-2-(4-chloro-
phenyl)acrylate (10a). White powder, 1H NMR (300
MHz, d6-DMSO): 1.20 (t, J = 7.1 Hz, 3H); 4.17 (q,
J = 7.1 Hz, 2H); 7.28 (d, J = 9.0 Hz, 2H); 7.34
(d, J = 9.0 Hz, 2H); 7.38 (d, J = 8.9 Hz, 2H); 7.45 (d,
J = 8.9 Hz, 2H); 7.63 (d, J = 12.7 Hz, 1H); 10.27 (d,
J = 12.9 Hz, 1H); MS (ESI): 380.0 (C17H16BrClNO2,
[M+H]+). Anal. Calcd for C17H15BrClNO2: C, 53.64;
H, 3.97; N, 3.68; Found: C, 53.66; H, 3.98; N, 3.67.
4.2.8. (Z)-Ethyl 3-(3,5-difluorophenylamino)-2-(4-meth-
oxyphenyl)acrylate (7a). White powder, 1H NMR
(300 MHz, d6-DMSO): 1.18 (t, J = 7.1 Hz, 3H); 3.73
(s, 3H); 4.16 (q, J = 7.1 Hz, 2H); 6.73 (t, J = 9.5 Hz,
1H); 6.85 (d, J = 8.7 Hz, 2H); 7.12 (d, J = 7.8 Hz, 2H);
7.25 (d, J = 8.7 Hz, 2H); 7.54 (d, J = 12.2 Hz, 1H);
10.23 (d, J = 12.7 Hz, 1H); MS (ESI): 334.0
(C18H18F2NO3,
[M+H]+).
Anal.
Calcd
for
C18H17F2NO3: C, 64.86; H, 5.14; N, 4.20; Found: C,
64.88; H, 5.12; N, 4.19.
4.2.15. (E)-Ethyl 3-(4-bromophenylamino)-2-(4-chloro-
phenyl)acrylate (10b). Colorless crystal, H NMR (300
1
4.2.9. (E)-Ethyl 3-(3,5-difluorophenylamino)-2-(4-meth-
oxyphenyl)acrylate (7b). Colorless crystal, 1H NMR
(300 MHz, d6-DMSO): 1.18 (t, J = 7.1 Hz, 3H); 3.77
(s, 3H); 4.08 (q, J = 7.1 Hz, 2H); 6.70 (t, J = 9.4 Hz,
1H); 6.90 (d, J = 9.7 Hz, 2H); 6.95 (d, J = 8.7 Hz, 2H);
7.14 (s, J = 8.7 Hz, 2H); 7.90 (s, J = 12.8 Hz, 1H); 8.70
(d, J = 12.9 Hz, 1H); MS (ESI): 334.1 (C18H18F2NO3,
[M+H]+). Anal. Calcd for C18H17F2NO3: C, 64.86; H,
5.14; N, 4.20; Found: C, 64.87; H, 5.13; N, 4.19.
MHz, d6-DMSO): 1.17 (t, J = 7.1 Hz, 3H); 4.08 (q,
J = 7.1 Hz, 2H); 7.12 (d, J = 8.6 Hz, 2H); 7.24
(d, J = 8.5 Hz, 2H); 7.43 (d, J = 8.4 Hz, 4H); 7.98 (d,
J = 13.0 Hz, 1H); 8.76 (d, J = 13.2 Hz, 1H); MS (ESI):
380.1 (C17H16BrClNO2, [M+H]+). Anal. Calcd for
C17H15BrClNO2: C, 53.64; H, 3.97; N, 3.68; Found: C,
53.63; H, 3.98; N, 3.66.
4.2.16. (Z)-Ethyl 3-(3,5-difluorophenylamino)-2-(4-chloro-
phenyl)acrylate (11a). Colorless crystal, H NMR (300
1
4.2.10. (Z)-Ethyl 3-(4-bromophenylamino)-2-(4-methoxy-
phenyl)acrylate (8a). White powder, 1H NMR (300
MHz, d6-DMSO): 1.19 (t, J = 7.1 Hz, 3H); 3.74 (s,
3H); 4.16 (q, J = 7.1 Hz, 2H); 6.87 (d, J = 8.6 Hz, 2H);
7.24 (d, J = 8.8 Hz, 2H); 7.25 (d, J = 8.5 Hz, 2H); 7.44
(d, J = 8.9 Hz, 2H); 7.51 (d, J = 12.7 Hz, 1H); 10.19
(d, J = 12.4 Hz, 1H); MS (ESI): 376.1 (C18H19BrNO3,
[M+H]+). Anal. Calcd for C18H18BrNO3: C, 57.46; H,
4.82; N, 3.72; Found: C, 57.44; H, 4.80; N, 3.73.
MHz, d6-DMSO): 1.19 (t, J = 7.1 Hz, 3H); 4.18 (q,
J = 7.1 Hz, 2H); 6.77 (d, J = 9.3 Hz, 1H); 7.17
(d, J = 8.1 Hz, 2H); 7.34 (d, J = 8.9 Hz, 2H); 7.38 (d,
J = 8.4 Hz, 2H); 7.65 (d, J = 12.5 Hz, 1H); 10.30 (d,
J = 12.8 Hz, 1H); MS (ESI): 338.1 (C17H15ClF2NO2,
[M+H]+). Anal. Calcd for C17H14ClF2NO2: C, 60.45;
H, 4.18; N, 4.15; Found: C, 60.48; H, 4.19; N, 4.16.
4.2.17. (E)-Ethyl 3-(3,5-difluorophenylamino)-2-(4-chloro-
phenyl)acrylate (11b). Colorless crystal, H NMR (500
1
4.2.11. (E)-Ethyl 3-(4-bromophenylamino)-2-(4-methoxy-
phenyl)acrylate (8b). Colorless crystal, 1H NMR (300
MHz, d6-DMSO): 1.17 (t, J = 7.1 Hz, 3H); 3.77 (s,
3H); 4.07 (q, J = 6.9 Hz, 2H); 6.95 (d, J = 8.6 Hz, 2H);
7.11 (d, J = 8.3 Hz, 2H); 7.14 (d, J = 8.4 Hz, 2H); 7.41
(d, J = 8.7 Hz, 2H); 7.94 (d, J = 12.8 Hz, 1H); 8.55 (d,
J = 13.0 Hz, 1H); MS (ESI): 376.0 (C18H19BrNO3,
[M+H]+). Anal. Calcd for C18H18BrNO3: C, 57.46; H,
4.82; N, 3.72; Found: C, 57.47; H, 4.80; N, 3.71.
MHz, d6-DMSO): 1.19 (t, J = 7.2 Hz, 3H); 4.11 (q,
J = 7.2 Hz, 2H); 6.75 (d, J = 9.1 Hz, 1H); 6.94
(d, J = 9.1 Hz, 2H); 7.26 (d, J = 8.3 Hz, 2H); 7.46 (d,
J = 8.3 Hz, 2H); 7.97 (d, J = 12.9 Hz, 1H); 8.87 (d,
J = 13.0 Hz, 1H); MS (ESI): 338.0 (C17H15ClF2NO2,
[M+H]+). Anal. Calcd for C17H14ClF2NO2: C, 60.45;
H, 4.18; N, 4.15; Found: C, 60.42; H, 4.18; N, 4.17.
4.2.18. (Z)-Ethyl 3-(3,5-dichlorophenylamino)-2-(4-chloro-
phenyl)acrylate (12a). White powder, 1H NMR (500
MHz, d6-DMSO): 1.22 (t, J = 7.1 Hz, 3H); 4.20 (q,
J = 7.1 Hz, 2H); 7.15 (s, 1H); 7.37 (d, J = 8.4 Hz, 2H);
7.41 (d, J = 8.4 Hz, 2H); 7.52 (s, 2H); 7.71 (d,
J = 12.6 Hz, 1H); 10.28 (d, J = 12.5 Hz, 1H); MS
(ESI): 370.0 (C17H15Cl3NO2, [M+H]+). Anal. Calcd
for C17H14Cl3NO2: C, 55.09; H, 3.81; N, 3.78; Found:
C, 55.13; H, 3.80; N, 3.75.
4.2.12. (Z)-Ethyl 3-(4-hydroxyphenylamino)-2-(4-meth-
oxyphenyl)acrylate (9a). Colorless crystal, 1H NMR
(300 MHz, d6-DMSO): 1.18 (t, J = 7.1 Hz, 3H); 3.73
(s, 3H); 4.14 (q, J = 7.0 Hz, 2H); 6.71 (d, J = 8.7 Hz,
2H); 6.85 (d, J = 8.7 Hz, 2H); 7.06 (d, J = 8.7 Hz, 2H);
7.23 (d, J = 8.4 Hz, 2H); 7.40 (d, J = 13.0 Hz, 1H);
10.09 (d, J = 12.8 Hz, 1H); MS (ESI): 314.1
(C18H20NO4, [M+H]+). Anal. Calcd for C18H19NO4:
C, 68.99; H, 6.11; N, 4.47; Found: C, 69.01; H, 6.09;
N, 4.48.
4.2.19. (E)-Ethyl 3-(3,5-dichlorophenylamino)-2-(4-chloro-
phenyl)acrylate (12b). Colorless crystal, H NMR (500
1
MHz, d6-DMSO): 1.19 (t, J = 6.9 Hz, 3H); 4.12 (q,
J = 7.0 Hz, 2H); 7.11 (s, 1H); 7.26 (d, J = 7.9 Hz, 2H);
7.27 (s, 2H); 7.46 (d, J = 8.2 Hz, 2H); 7.97 (d,
J = 12.9 Hz, 1H); 8.81 (d, J = 12.9 Hz, 1H); MS (ESI):
370.1 (C17H15Cl3NO2, [M+H]+). Anal. Calcd for
C17H14Cl3NO2: C, 55.09; H, 3.81; N, 3.78; Found: C,
55.12; H, 3.82; N, 3.80.
4.2.13. (E)-Ethyl 3-(4-hydroxyphenylamino)-2-(4-meth-
oxyphenyl)acrylate (9b). Colorless crystal, 1H NMR
(300 MHz, d6-DMSO): 1.15 (t, J = 7.1 Hz, 3H); 3.76 (s,
3H); 4.04 (q, J = 7.1 Hz, 2H); 6.67 (d, J = 8.8 Hz, 2H);
6.93 (d, J = 8.7 Hz, 2H); 6.96 (d, J = 8.6 Hz, 2H); 7.13
(d, J = 8.7 Hz, 2H); 7.87 (d, J = 13.6 Hz, 1H); 8.23 (d,