1
White solid, yield: 55.6%. Mp: 144–146 °C. H NMR (400
δ 159.5, 155.9, 153.4 (d, J = 242.6 Hz), 151.7, 149.3, 148.8,
146.1, 140.0 (d, J = 9.5 Hz), 136.5, 133.4 (d, J = 12.5 Hz), 130.5,
130.4 (2C), 128.8, 128.5 (2C), 123.5, 114.4, 108.5, 106.3 (d, J =
23.3 Hz), 101.8, 99.0, 66.4, 65.4 (2C), 57.2, 55.7, 54.5, 52.7 (2C),
24.9, 20.6. ESI-MS: m/z 661.2 [M+Na]+.
MHz, DMSO-d6) δ 9.06 (s, 1 H), 8.49 (d, J = 4.8 Hz, 1 H), 7.72
(d, J = 12.8 Hz, 1 H), 7.54 (s, 1 H), 7.41 (m, 1 H), 7.26–7.17 (m,
7 H), 6.47 (d, J = 4.8 Hz), 4.73 (s, 2 H), 4.17 (t, J = 6.0 Hz, 2 H),
3.96 (s, 3 H), 1.81–1.79 (m, 2 H), 1.53–1.47 (m, 2 H), 0.98 (t, J =
6.8 Hz, 3 H). 13C NMR (100 MHz, DMSO-d6) δ 162.1 (d, J =
243.5 Hz), 159.5, 153.3 (d, J = 254.8 Hz), 151.9, 150.9, 149.6,
148.3, 145.8, 137.4 (d, J = 8.9 Hz), 135.2 (d, J = 14.3 Hz), 132.7
(2C), 125.4, 124.0, 115.8, 115.4 (d, J = 18.5 Hz, 2C), 114.3,
107.8 (d, J = 20.7 Hz), 107.4, 101.9, 98.9, 67.9, 57.1, 55.7, 30.4,
18.7, 13.6. ESI-MS: m/z 594.1 [M+H]+.
4.1.12.20 1-{3-Fluoro-4-[6-methoxy-7-(3-piperidin-1-yl-prop-
oxy)quinolin-4-yloxy]phenyl}-3-[(phenylmethane)-sulfonyl]-
urea (13t)
1
White solid, yield: 52.8%. Mp: 134–136 °C. H NMR (400
MHz, DMSO-d6) δ 8.74 (s, 1 H), 8.46 (d, J = 4.8 Hz, 1 H), 7.85
(d, J = 14.4 Hz, 1 H), 7.56 (s, 1 H), 7.42 (s, 1 H), 7.32–7.21 (m, 7
H), 6.43 (d, J = 4.8 Hz, 1 H), 4.36 (s, 2 H), 4.24 (t, 2 H), 3.96 (s,
3 H), 3.50 (m, 2 H), 3.11 (m, 4 H), 2.19 (m, 2 H), 1.70 (m, 4 H),
1.53 (m, 2 H). 13C NMR (100 MHz, DMSO-d6) δ 159.7, 158.6,
153.4 (d, J = 241.5 Hz), 151.3, 149.2, 148.9, 146.1, 141.7 (d, J =
10.6 Hz), 133.4, 132.2 (d, J = 12.8 Hz), 130.4 (2C), 127.7 (2C),
126.6, 123.2, 114.6, 113.7, 108.7, 105.4 (d, J = 23.4 Hz), 101.8,
99.1, 66.0, 57.1, 55.7, 53.9, 52.5 (2C), 23.7, 23.1 (2C), 21.7. ESI-
MS: m/z 623.2 [M+H]+.
4.1.12.16 1-[4-(7-Butoxy-6-methoxyquinolin-4-yloxy)-3-fluor-
ophenyl]-3-[(4-methylphenylmethane)-sulfonyl]-urea (13p)
1
White solid, yield: 49.4%. Mp: 164–166 °C. H NMR (400
MHz, DMSO-d6) δ 9.06 (s, 1 H), 8.48 (d, J = 4.8 Hz, 1 H), 7.70
(d, J = 12.8 Hz, 1 H), 7.53 (s, 1 H), 7.40 (m, 1 H), 7.25–7.16 (m,
7 H), 6.46 (d, J = 4.8 Hz, 1 H), 4.72 (s, 2 H), 4.16 (t, J = 6.0 Hz,
2 H), 3.95 (s, 3 H), 2.30 (s, 3 H), 1.80–1.79 (m, 2 H), 1.52–1.47
(m, 2 H), 0.97 (t, J = 6.8 Hz, 3 H). 13C NMR (100 MHz, DMSO-
d6) δ 159.3, 154.2 (d, J = 241.4 Hz), 152.0, 150.7, 149.5, 148.5,
146.0, 137.7 (d, J = 11.7 Hz), 137.0, 135.3 (d, J = 12.9 Hz),
130.5 (2C), 129.0 (2C), 126.3, 123.9, 115.8, 114.3, 108.1, 107.8
(d, J = 23.4 Hz), 101.9, 98.9, 67.9, 57.7, 55.6, 30.4, 20.6, 18.6,
13.5. ESI-MS: m/z 568.2 [M+H]+.
4.1.12.21 1-{3-Fluoro-4-[6-methoxy-7-(3-piperidin-1-yl-prop-
oxy)quinolin-4-yloxy]phenyl}-3-[(4-fluorophenylmethane)-
sulfonyl]-urea (13u)
1
Light yellow solid, yield: 46.8%. Mp: 148–150 °C. H NMR
4.1.12.17 1-{3-Fluoro-4-[6-methoxy-7-(3-morpholin-4-yl-pro-
poxy)quinolin-4-yloxy]phenyl}-3-[(phenylmethane)-sulfonyl]-
urea (13q)
(400 MHz, DMSO-d6) δ 8.76 (s, 1 H), 8.46 (d, J = 5.2 Hz, 1 H),
7.85 (dd, J = 2.4, 14.4 Hz, 1 H), 7.56 (s, 1 H), 7.43 (s, 1 H),
7.33–7.19 (m, 4 H), 7.11 (t, J = 8.8 Hz, 1 H), 6.43 (d, J = 5.2 Hz,
1 H), 4.34 (s, 2 H), 4.24 (t, J = 6.0 Hz, 2 H), 3.96 (s, 3 H), 3.16
(m, 6 H), 2.22 (t, J = 6.8 Hz, 2 H), 1.72 (m, 2 H), 1.56–1.53 (m, 2
H). 13C NMR (100 MHz, DMSO-d6) δ 161.3 (d, J = 240.9 Hz),
159.7, 158.6, 153.4 (d, J = 241.1 Hz), 151.3, 149.2, 148.9, 146.1,
141.6 (d, J = 10.1 Hz), 132.4, 132.2 (d, J = 7.8 Hz, 2C), 129.7,
123.2, 114.6 (d, J = 5.9 Hz, 2C), 114.3, 113.7, 108.7, 105.5 (d, J
= 21.9 Hz), 101.8, 99.1, 66.0, 56.2, 55.7 (2C), 53.8, 52.4, 23.6,
22.9 (2C), 21.5. ESI-MS: m/z 641.2 [M+H]+.
1
Light yellow solid, yield: 63.1%. Mp: 124–126 °C. H NMR
(400 MHz, DMSO-d6) δ 8.82 (s, 1 H), 8.46 (d, J = 5.2 Hz, 1 H),
7.82 (d, J = 14.8 Hz, 1 H), 7.54 (s, 1 H), 7.40 (s. 1 H), 7.36–7.30
(m, 8 H), 6.43 (d, J = 5.2 Hz, 1 H), 4,54 (s, 2 H), 4.44 (m, 2 H),
4.21 (t, J = 6.4 Hz, 2 H), 4.09–4.04 (q, J = 7.2 Hz, 2 H), 3.95 (s,
3 H), 3.63 (t, J = 4.4 Hz, 4 H), 2.65–2.62 (m, 2 H), 2.06–1.98 (m,
2 H). 13C NMR (100 MHz, DMSO-d6) δ 159.6, 156.9, 153.4 (d, J
= 247.3 Hz), 151.6, 149.3, 148.8, 146.1, 140.7 (d, J = 10.1 Hz),
133.0 (d, J = 12.7 Hz), 132.4, 130.5 (2C), 128.2 (2C), 127.8,
127.0, 123.4, 114.4, 108.5, 106.0 (d, J = 22.9 Hz), 101.7, 99.0,
66.4, 65.3 (2C), 57.3, 55.7, 54.4, 52.7 (2C), 24.8. ESI-MS: m/z
625.2 [M+H]+.
4.1.12.22 1-{3-Fluoro-4-[6-methoxy-7-(3-piperidin-1-yl-prop-
oxy)quinolin-4-yloxy]phenyl}-3-[(4-methylphenylmethane)-
sulfonyl]-urea (13v)
1
Yellow solid, yield: 51.2%. Mp: 140–142 °C. H NMR (400
4.1.12.18 1-{3-Fluoro-4-[6-methoxy-7-(3-morpholin-4-yl-pro-
poxy)quinolin-4-yloxy]phenyl}-3-[(4-flurorphenylmethane)-
sulfonyl]-urea (13r)
MHz, DMSO-d6) δ 8.78 (s, 1 H), 8.47 (d, J = 5.2 Hz, 1 H), 7.82
(d, J = 14.4 Hz, 1 H), 7.56 (s, 1 H), 7.43 (s, 1 H), 7.30–7.09 (m, 7
H), 6.44 (d, J = 5.2 Hz, 1 H), 4.37 (s, 2 H), 4.25 (t, J = 5.6 Hz, 2
H), 3.96 (s, 3 H), 3.19 (m, 6 H), 2.27 (s, 3 H), 2.24–2.23 (m, 2 H),
1.73 (m, 4 H), 1.56–1.50 (m, 2 H). 13C NMR (100 MHz, DMSO-
d6) δ 159.6, 157.9, 153.4 (d, J = 241.7 Hz), 151.3, 149.2, 148.8,
146.0, 141.3 (d, J = 7.3 Hz), 137.0, 135.8, 130.4, 130.2 (2C),
128.6, 128.2 (2C), 123.2, 114.6, 108.7, 105.5 (d, J = 25.3 Hz),
101.8, 99.1, 65.9, 56.8, 55.7 (2C), 53.8, 52.4, 23.6, 22.9 (2C),
21.5, 20.5. ESI-MS: m/z 659.2 [M+Na]+.
1
Light yellow solid, yield: 48.4%. Mp: 145–147 °C. H NMR
(400 MHz, DMSO-d6) δ 8.95 (s, 1 H), 8.47 (d, J = 5.2 Hz, 1 H),
7.79 (d, J = 13.2 Hz, 1 H), 7.54 (s, 1 H), 7.41(s, 1 H), 7.39–7.14
(m, 6 H), 6.44 (d, J = 4.8 Hz, 1 H), 4.52 (s, 2 H), 4.23 (t, J = 6.0
Hz, 2 H), 3.95 (s, 3 H), 3.70 (m, 4 H), 2.83–2.79 (m, 6 H), 2.11-
2.08 (m, 2 H). 13C NMR (100 MHz, DMSO-d6) δ 161.6 (d, J =
241.9 Hz), 159.5, 153.4 (d, J = 242.5 Hz), 151.6, 149.3, 148.8,
146.1, 140.0, 139.9, 133.5 (d, J = 12.4 Hz), 132.4 (d, J = 8.2 Hz,
2C), 129.4, 128.1, 123.5, 114.7 (d, J = 21.2 Hz, 2C), 114.5, 108.5,
106.4 (d, J = 23.0 Hz), 101.8, 99.0, 66.2, 64.9 (2C), 56.6, 55.7,
54.3, 52.4 (2C), 24.4. ESI-MS: m/z 643.2 [M+H]+.
4.1.12.23 1-{3-Fluoro-4-[6-methoxy-7-(3-pyrrolidin-1-yl-prop-
oxy)quinolin-4-yloxy]-phenyl}-3-[(phenylmethane)-sulfonyl]-
urea (13w)
1
Yellow solid, yield: 48.4%. Mp: 159–161 °C. H NMR (400
4.1.12.19 1-{3-Fluoro-4-[6-methoxy-7-(3-morpholin-4-yl-pro-
poxy)quinolin-4-yloxy]phenyl}-3-[(4-methylphenylmethane)-
sulfonyl]-urea (13s)
MHz, DMSO-d6) δ 8.74 (s, 1 H), 8.47 (d, J = 5.2 Hz, 1 H), 7.86
(dd, J = 2.4, 14.4 Hz, 1 H), 7.57 (s, 1 H), 7.43 (s, 1 H), 7.33–7.20
(m, 8 H), 6.44 (d, J = 4.8 Hz, 1 H), 4.36 (s, 2 H), 4.26 (t, J = 6.0
Hz, 2 H), 3.97 (s, 3 H), 3.29-3.27 (m, 6 H), 2.23–2.16 (m, 2 H),
1.78–1.74 (m, 4 H). 13C NMR (100 MHz, DMSO-d6) δ 159.7,
158.6, 153.4 (d, J = 241.3 Hz), 151.3, 149.2, 148.9, 146.1, 141.6
(d, J = 10.3 Hz), 133.3, 132.3 (d, J = 12.5 Hz), 130.4 (2C), 127.7
(2C), 126.6, 123.2, 114.6, 113.7, 108.7, 105.5 (d, J = 22.8 Hz),
1
Light yellow solid, yield: 54.4%. Mp: 154–156 °C. H NMR
(400 MHz, DMSO-d6) δ 8.89 (s, 1 H), 8.46 (d, J = 5.2 Hz, 1 H),
7.80 (d, J = 13.6 Hz, 1 H), 7.54 (s, 1 H), 7.40 (s, 1 H), 7.29–7.12
(m, 6 H), 6.43 (d, J = 5.2 Hz, 1 H), 4,45 (s, 2 H), 4.21 (t, J = 6.4
Hz, 1 H), 3.95 (s, 3 H), 3.65–3.64 (m, 4 H), 2.67–2.61 (m, 6 H),
2.28 (s, 3 H), 2.08-2.03 (m, 2 H). 13C NMR (100 MHz, DMSO-d6)