Molecules 2021, 26, 3496
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1H NMR (400 MHz, DMSO-d6)
δ
8.72 (s, 1H), 8.34 (d, J = 5.7 Hz, 1H), 7.77 (dd, J = 6.8,
2.4 Hz, 1H), 7.32–7.18 (m, 2H), 7.14 (d, J = 5.7 Hz, 1H), 7.04 (d, J = 8.2 Hz, 1H), 6.93 (d,
J = 2.0 Hz, 1H), 6.80 (dd, J = 8.2, 1.9 Hz, 1H), 6.63 (t, J = 5.8 Hz, 1H), 5.13 (s, 2H), 4.91 (q,
J = 8.7 Hz, 2H), 4.22 (d, J = 5.7 Hz, 2H), 3.74 (s, 3H), 2.22 (s, 3H).; 13C NMR (101 MHz,
DMSO-d6)
δ 161.81, 155.94, 155.44, 152.33 (d, J = 240.0 Hz), 149.59, 148.04, 147.15, 138.26 (d,
J = 2.8 Hz), 124.27 (q, J = 277.4 Hz), 122.05, 119.69, 119.44 (d, J = 18.9 Hz), 119.31, 118.23
(d, J = 6.5 Hz), 117.13 (d, J = 21.3 Hz), 114.26, 112.08, 108.06, 71.55, 65.08 (q, J = 34.2 Hz),
56.00, 43.09, 10.35; IR: 3313, 2944, 2883, 1641, 1564, 1500, 1477, 1420, 1390, 1308, 1258, 1209,
1164, 1131, 1008, 970, 911, 862, 800, 757, 647, 576, 445; HRMS: 526.116220([M
−
H]−) for
C24H21ClF4N3O4, 528.130773([M + H]+) for C24H23ClF4N3O4.
1-(3-methoxy-4-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)benzyl)-3-(4-(trifluorom
ethyl)phenyl)urea (8c), white powder 0.78 g, yield 72%; m.p: 169.9–171.0 ◦C; MS:544.5([M +
H]+), 566.1([M + Na]+); 1H NMR (400 MHz, DMSO-d6)
δ 8.95 (s, 1H), 8.34 (d, J = 5.7 Hz, 1H),
7.59 (q, J = 8.8 Hz, 4H), 7.14 (d, J = 5.7 Hz, 1H), 7.05 (d, J = 8.2 Hz, 1H), 6.95 (d, J = 2.0 Hz,
1H), 6.82 (dd, J = 8.2, 1.9 Hz, 1H), 6.69 (t, J = 5.8 Hz, 1H), 5.14 (s, 2H), 4.91 (q, J = 8.7 Hz, 2H),
4.24 (d, J = 5.7 Hz, 2H), 3.74 (s, 3H), 2.22 (s, 3H). 13C NMR (101 MHz, DMSO-d6)
δ 161.81,
155.93, 155.25, 149.61, 148.03, 147.19, 144.64, 133.47, 126.37, 125.09 (q, J = 270.6 Hz), 124.26
(q, J = 277.5 Hz), 122.06, 119.73, 117.72, 114.26, 112.10, 108.05, 71.55, 65.09 (q, J = 35.0 Hz),
55.98, 43.10, 10.31; IR: 3414, 3376, 2940, 2886, 1703, 1686, 1581, 1534, 1512, 1477, 1408, 1321,
1256, 1220, 1180, 1155, 1135, 1102, 1063, 1008, 979, 862, 842, 812, 595, 554;HRMS: 542.151999
([M − H]−) for C25H22F6N3O4, 544.166552([M + H]+)+ for C25H24F6N3O4.
1-(3-methoxy-4-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)benzyl)-3-(3-(trifluorom
◦
ethyl)phenyl)urea (8d), white powder 0.83 g, yield 76%; m.p.: 153.2–154.2 C; MS:544.2([M +
H]+), 542.0([M
−
H]−); 1H NMR (400 MHz, DMSO-d6)
δ
8.90 (s, 1H), 8.34 (d, J = 5.7 Hz,
1H), 7.98 (s, 1H), 7.52 (d, J = 8.3 Hz, 1H), 7.45 (t, J = 7.9 Hz, 1H), 7.23 (d, J = 7.6 Hz, 1H), 7.14
(d, J = 5.7 Hz, 1H), 7.04 (d, J = 8.2 Hz, 1H), 6.94 (d, J = 1.9 Hz, 1H), 6.81 (dd, J = 8.2, 1.9 Hz,
1H), 6.68 (t, J = 5.9 Hz, 1H), 5.13 (s, 2H), 4.91 (q, J = 8.7 Hz, 2H), 4.23 (d, J = 5.8 Hz, 2H), 3.74
(s, 3H), 2.22 (s, 3H). 13C NMR (101 MHz, DMSO-d6)
δ 161.82, 155.94, 155.46, 149.62, 148.02,
147.18, 141.80, 133.59, 130.11, 124.73 (q, J = 272.3 Hz), 124.25 (q, J = 277.4 Hz), 122.07, 121.62,
119.69, 117.68, 114.28, 114.06, 112.08, 108.02 (d, J = 4.4 Hz), 71.56, 65.10 (q, J = 34.2 Hz), 55.97
(d, J = 3.2 Hz), 43.08, 10.33; IR: 3412, 3374, 2940, 2876, 1702, 1582, 1551, 1514, 1477, 1442,
1380, 1341, 1312, 1255, 1221, 1182, 1158, 1−111, 1067, 1028, 1007, 979, 891, 864, 813, 796, 702,
664, 597, 552; HRMS: 542.151999([M
C25H24F6N3O4.
−
H] ) for C25H22F6N3O4+, 544.161552 ([M + H]+) for
1-(3-methoxy-4-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)benzyl)-3-(4-methoxyph
enyl)urea (8e), −white powder 0.59 g, yield 58%; m.p.: 179.5–180.3 ◦C; MS:566.2 ([M + H]+),
504.0([M
−
H] ); 1H NMR (400 MHz, DMSO-d6)
δ 8.28 (s, 1H), 7.29 (d, J = 8.9 Hz, 2H), 7.14
(d, J = 5.7 Hz, 1H), 6.93 (d, J = 1.9 Hz, 1H), 6.81 (dd, J = 9.0, 7.1 Hz, 3H), 6.40 (t, J = 5.9 Hz,
1H), 5.13 (s, 2H), 4.92 (q, J = 8.8 Hz, 2H), 4.20 (d, J = 5.8 Hz, 2H), 3.70 (s, 3H), 2.22 (s, 3H). 13
NMR (101 MHz, DMSO-d6) 161.80, 155.96, 155.86, 154.40, 149.57, 148.05, 147.08, 134.08,
C
δ
133.97, 124.28 (d, J = 277.9 Hz), 122.05, 119.91, 119.64, 114.33, 114.27, 112.06, 108.07, 71.58,
65.08 (q, J = 34.5 Hz), 55.99, 55.59, 43.09, 10.36; IR: 3312, 2940, 2839, 1631, 1571, 1508, 1467,
1417, 1376, 1363, 1308, 1271, 1241, 1160, 1136, 1030, 973, 862, 827, 669, 578, 524, 423; HRMS:
504.175179 ([M − H]−) for C25H25F3N3O5, 506.189732 ([M + H]+) for C25H27F3N3O5.
1-(3-methoxy-4-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)benzyl)-3-(3-nitropheny
l)urea (8f), yell−ow powder 0.31 g, yield 30%; m.p.: 168.9–170.5 ◦C; MS: 521.2 ([M + H]+),
519.0([M
−
H] ); 1H NMR (400 MHz, DMSO-d6)
δ 9.08 (s, 1H), 8.52 (t, J = 2.2 Hz, 1H), 8.33
(d, J = 5.8 Hz, 1H), 7.75 (d, J = 8.3 Hz, 1H), 7.66 (d, J = 8.4 Hz, 1H), 7.50 (dd, J = 9.1, 7.3 Hz,
1H), 7.13 (d, J = 5.9 Hz, 1H), 7.04 (d, J = 8.2 Hz, 1H), 6.96–6.92 (m, 1H), 6.85–6.71 (m, 2H),
5.13 (s, 2H), 4.91 (q, J = 8.8 Hz, 2H), 4.24 (d, J = 5.9 Hz, 2H), 3.74 (s, 3H), 2.21 (s, 3H). 13
C
NMR (101 MHz, DMSO-d6) δ 161.83, 155.93, 155.35, 149.63, 148.59, 148.02, 147.20, 142.28,
133.51, 130.31, 124.26 (q, J = 277.8 Hz), 124.16, 122.07, 119.74, 115.95, 114.32, 112.14, 112.06,
108.05, 71.56, 65.11 (q, J = 34.4 Hz), 56.02, 43.11, 10.34; IR: 3410, 3010, 2943, 2882, 2832, 1701,