Molecules 2014, 19
2024
1-(3-tert-Butyl-1-(4-chlorophenyl)-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-chromen-8-yl)-
1
urea (40c). Yield: 29%, white solid, H-NMR (CDCl3, 400 MHz), δ: 7.65 (d, 1H, J = 8.8 Hz), 7.43
(d, 2H), 7.35 (d, 2H, J = 8.8 Hz), 7.10 (s, 1H), 6.74 (d, 1H, J = 10.0 Hz), 6.68 (s, 1H), 6.36–6.38 (m, 2H),
5.72 (m, 1H), 4.69 (t, 2H, J = 2.0 Hz), 4.10 (t, 2H, J = 5.2 Hz), 3.74 (t, 4H, J = 4.4 Hz), 2.81 (t, 2H,
J = 4.8 Hz), 2.59 (t, 4H), 1.35 (s, 9H). FAB-MS (m/z): 552.2 [M+H]+.
1-(1-(4-Bromophenyl)-3-tert-butyl-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-chromen-8-yl)-
1
urea (40d). Yield: 26%, white solid, H-NMR (CDCl3, 400 MHz), δ: 7.65 (d, 1H), 7.50 (d, 2H,
J = 8.8 Hz), 7.36 (d, 2H, J = 8.8 Hz), 7.12 (s, 1H), 6.77 (s, 1H), 6.73 (d, 1H, J = 10.4 Hz), 6.38 (d, 1H,
J = 7.2 Hz), 6.36 (s, 1H), 5.72 (m, 1H), 4.69 (t, 2H, J = 1.6 Hz), 4.10 (t, 2H, J = 1.6 Hz), 3.74 (t, 4H,
J = 4.4 Hz), 2.82 (t, 2H, J = 4.8 Hz), 2.60 (t, 4H), 1.34 (s, 9H). FAB-MS (m/z): 598.0 [M+H]+.
1-(3-tert-Butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-chromen-8-yl)-
urea (40e). Yield: 26%, white solid, 1H-NMR (CDCl3, 400 MHz), δ:7.72 (d, 1H, J = 8.8 Hz), 7.33 (d,
2H, J = 9.2 Hz), 7.25 (s, 1H), 6.88 (d, 2H, J = 9.2 Hz), 6.75 (d, 1H), 6.73 (s, 1H), 6.36 (d, 1H), 6.33 (s,
1H), 5.70 (m, 1H), 4.67 (t, 2H, J = 1.6 Hz), 4.10 (t, 2H), 3.77 (s, 3H), 3.74 (t, 4H, J = 4.4 Hz), 2.80 (t,
2H, J = 5.6 Hz), 2.59 (t, 4H), 1.35 (s, 9H). FAB-MS (m/z): 548.1 [M+H]+.
1-(3-tert-Butyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-
1
chromen-8-yl)urea (40f). Yield: 17%, white solid, H-NMR (CDCl3, 400 MHz), δ: 7.65 (m, 5H),
7.07 (s, 1H), 6.76 (s, 1H), 6.73 (d, 1H, J = 9.6 Hz), 6.40 (s, 1H), 6.38 (d, 1H, J = 8.8 Hz), 5.70 (m,
1H), 4.70 (t, 2H, J = 1.6 Hz), 4.10 (t, 2H, J = 5.2 Hz), 3.74 (t, 4H, J = 4.0 Hz), 2.82 (t, 2H), 2.60 (t,
4H), 1.36 (s, 9H). FAB-MS (m/z): 586.1 [M+H]+.
1-(3-tert-Butyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-chromen-8-yl)urea
(40g). Yield: 37%, white solid, 1H-NMR (CDCl3, 400 MHz), δ: 8.18 (d, 2H, J = 9.2 Hz), 7.74 (d, 2H,
J = 8.8 Hz), 7.55 (d, 1H), 7.30 (s, 1H), 6.71 (d, 1H, J = 10.0 Hz), 6.39 (s, 1H), 6.34 (d, 1H, J = 9.2 Hz),
5.70 (m, 1H), 4.68 (t, 2H, J = 1.6 Hz), 4.09 (t, 2H, J = 6.0 Hz), 3.74 (t, 4H, J = 4.4 Hz), 2.81 (t, 2H,
J = 6.0 Hz), 2.60 (t, 4H), 1.34 (s, 9H). FAB-MS (m/z): 563.0 [M+H]+.
1-(3-tert-Butyl-1-(4-ethylphenyl)-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-chromen-8-yl)urea
(40h). Yield: 27%, white solid, 1H-NMR (CDCl3, 400 MHz), δ: 7.74 (d, 1H, J = 8.8 Hz), 7.36 (d, 2H,
J = 8.4 Hz), 7.25 (d, 2H), 7.14 (s, 1H), 6.73 (d, 1H, J = 10.0 Hz), 6.35–6.40 (m, 3H), 5.72 (m, 1H),
4.71 (t, 2H, J = 2.0 Hz), 4.12 (t, 2H), 3.75 (t, 4H), 2.84 (t, 2H), 2.62–2.68 (m, 6H), 1.36 (s, 9H), 1.22
(t, 3H). FAB-MS (m/z): 546.0 [M+H]+.
1-(3-tert-Butyl-1-(4-isopropylphenyl)-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-chromen-8-yl)-
urea (40i). Yield: 19%, white solid, 1H-NMR (CDCl3, 400 MHz), δ: 7.74 (d, 1H, J = 9.2 Hz), 7.34 (d, 2H),
7.26 (d, 2H), 7.15 (s, 1H), 6.73 (d, 1H, J = 10.0 Hz), 6.43 (s, 1H), 6.39 (d, 1H, J = 9.2 Hz), 6.35 (s,
1H), 5.72 (m, 1H), 4.71 (t, 2H, J = 2.0 Hz), 4.09 (t, 2H, J = 5.2 Hz), 3.73 (t, 4H), 2.81 (t, 2H), 2.59 (t,
4H), 1.36 (s, 9H), 1.24 (d, 3H), 1.22 (d, 3H). FAB-MS (m/z): 560.1 [M+H]+.
1-(3-tert-Butyl-1-(3-chloro-4-fluorophenyl)-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-chromen-
8-yl)urea (40j). Yield: 27%, white solid, 1H-NMR (CDCl3, 400 MHz), δ: 7.60 (m, 2H), 7.38 (m, 1H),