6
Journal of Chemistry
3-chloro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-
114.82, 108.81, 66.57, 60.79, 53.39; HRMS (m/z): calcd.
For C22H22FN4O3S (neutral M + H) 441.13966, found
441.15094.
yl)phenyl)benzamide 5d: White solid; yield, 74.5%; m.p.:
164.3°C–166.9°C; 1H NMR (400 MHz, DMSO-d6) δ 12.07
(s, 1H), 10.42 (d, J � 3.4 Hz, 1H), 8.39 (s, 1H), 8.01 (s, 1H),
7.95–7.88 (m, 1H), 7.69–7.49 (m, 5H), 7.41–7.36 (m, 1H),
3.58 (q, J � 4.1 Hz, 4H), 3.29 (s, 2H), 2.50 (d, J � 4.6 Hz,
4H); 13C NMR (101 MHz, DMSO-d6) δ 168.98, 164.47,
157.89, 149.15, 139.69, 137.23, 135.12, 133.65, 131.89,
130.89, 129.45, 127.84, 126.95, 121.84, 120.41, 118.47,
108.82, 66.57, 60.79, 53.39; HRMS (m/z): calcd. For
C22H22ClN4O3S (neutral M + H) 457.11011, found
457.12488.
N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)-3-
(trifluoromethyl)benzamide 5i: White solid; yield, 74.8%; m.
p.: 103.4°C–105.1°C; 1H NMR (400 MHz, DMSO-d6) δ 12.07
(s, 1H), 10.55 (d, J � 3.4 Hz, 1H), 8.38 (s, 1H), 8.30 (s, 1H),
8.26 (d, J � 8.0 Hz, 1H), 7.95 (d, J � 7.9 Hz, 1H), 7.82–7.72
(m, 1H), 7.64 (d, J � 7.9 Hz, 2H), 7.57 (d, J � 3.4 Hz, 1H),
7.42–7.38 (m, 1H), 3.57 (t, J � 4.3 Hz, 4H), 3.29 (s, 2H), 2.50
(d, J � 5.1 Hz, 4H); 13C NMR (101 MHz, DMSO-d6) δ 168.98,
164.43, 157.90, 149.11, 139.61, 136.10, 135.14, 133.65, 132.34,
130.50, 130.22, 129.75, 129.48, 128.65, 124.68, 124.64, 121.92,
120.50, 118.59, 108.84, 66.57, 60.80, 53.39; HRMS (m/z):
calcd. For C23H22F3N4O3S (neutral M + H) 491.13647, found
491.15257.
N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)-4-
(trifluoromethyl)benzamide 5j: White solid; yield, 76.7%; m.
p.: 146.9°C–148.8°C; 1H NMR (400 MHz, DMSO-d6) δ 12.07
(s, 1H), 10.61 (s, 1H), 8.41 (s, 1H), 8.16 (d, J � 7.7 Hz, 2H),
7.90 (d, J � 8.0 Hz, 2H), 7.63 (d, J � 8.1 Hz, 2H), 7.56 (d, J �
3.1 Hz, 1H), 7.39 (t, J � 7.9 Hz, 1H), 3.58 (d, J � 4.6 Hz, 4H),
3.29 (d, J � 3.2 Hz, 2H), 2.50 (d, J � 4.8 Hz, 4H); 13C NMR
(101 MHz, DMSO-d6) δ 169.05, 164.82, 158.03, 149.11,
139.64, 139.08, 135.16, 131.95, 131.64, 129.94, 129.46, 129.07,
125.90, 125.87, 125.83, 125.79, 125.71, 124.52, 123.00, 121.92,
120.46, 118.52, 108.80, 66.58, 60.84, 53.39; HRMS (m/z):
calcd. For C23H22F3N4O3S (neutral M + H) 491.13647, found
491.14793.
3-bromo-N-(3-(2-(2-morpholinoacetamido)thiazol-4-
yl)phenyl)benzamide 5e: White solid; yield, 74.6%; m.p.:
223.3°C–224.4°C; 1H NMR (400 MHz, DMSO-d6) δ 12.13
(s, 1H), 10.47 (s, 1H), 8.45 (s, 1H), 8.07 (s, 1H), 8.01–7.89
(m, 2H), 7.68 (d, J � 9.5 Hz, 3H), 7.61 (s, 1H), 7.44 (d, J �
6.9 Hz, 1H), 3.63 (s, 4H), 3.34 (d, J � 4.1 Hz, 2H), 2.56 (s,
4H); 13C NMR (101 MHz, DMSO-d6) δ 168.98, 164.47,
157.89, 149.15, 139.68, 137.22, 135.11, 133.64, 132.99,
131.89, 131.05, 130.89, 129.44, 129.24, 128.33, 127.84,
126.95, 121.83, 120.41, 118.47, 108.81, 66.57, 60.79, 53.39;
HRMS (m/z): calcd. For C22H22BrN4O3S (neutral M + H,
M + 2 + H) 501.05960, found 501.06635, 503.06461.
4-bromo-N-(3-(2-(2-morpholinoacetamido)thiazol-4-
yl)phenyl)benzamide 5f: White solid; yield, 74.6%; m.p.:
1
223.3°C–224.4°C; H NMR (400 MHz, DMSO-d6) δ 12.13
(s, 1H), 10.47 (s, 1H), 8.45 (s, 1H), 8.07 (s, 1H), 8.01–7.89
(m, 2H), 7.68 (d, J � 9.5 Hz, 3H), 7.61 (s, 1H), 7.44 (d, J �
6.9 Hz, 1H), 3.63 (s, 4H), 3.34 (d, J � 4.1 Hz, 2H), 2.56 (s,
4H); 13C NMR (101 MHz, DMSO-d6) δ 168.98, 164.47,
157.89, 149.15, 139.68, 137.22, 135.11, 133.64, 131.89,
130.89, 129.44, 127.84, 126.95, 121.83, 120.41, 118.47,
108.81, 66.57, 60.79, 53.39; HRMS (m/z): calcd. For
C22H22BrN4O3S (neutral M + H, M + 2 + H) 501.05960,
found 501.06635, 503.06462.
N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)furan-
2-carboxamide 5k: White solid; yield, 88.2%; m.p.: 189.5°C–
190.8°C; 1H NMR (400 MHz, DMSO-d6) δ 12.12 (s, 1H), 10.29
(s, 1H), 8.38 (t, J � 1.9 Hz, 1H), 7.97 (d, J � 1.6 Hz, 1H), 7.66 (t, J
� 1.9 Hz, 1H), 7.64 (t, J � 1.8 Hz, 1H), 7.59 (s, 1H), 7.42 (d, J �
7.9 Hz, 1H), 7.38 (d, J � 3.3 Hz, 1H), 6.74–6.73 (m, 1H), 3.62 (t, J
� 4.6 Hz, 4H), 3.33 (s, 2H), 2.54 (t, J � 4.6 Hz, 4H); 13C NMR
(101 MHz, DMSO-d6) δ 164.37, 153.28, 152.05, 144.56, 143.27,
141.65, 134.73, 130.50, 124.83, 117.05, 115.77, 113.84, 110.61,
108.01, 104.19, 61.98, 56.20, 48.79; HRMS (m/z): calcd. For
C20H21N4O4S (neutral M + H) 413.12835, found 413.13295.
2-methoxy-N-(3-(2-(2-morpholinoacetamido)thiazol-
4-yl)phenyl)acetamide 5l: Yellow solid; yield, 85.2%; m.
4-fluoro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-
yl)phenyl)benzamide 5g: White solid; yield, 75.4%; m.p.:
175.5°C–177.1°C; 1H NMR (400 MHz, DMSO-d6) δ 12.07
(s, 1H), 10.33 (d, J � 3.4 Hz, 1H), 8.39 (d, J � 3.2 Hz, 1H),
8.06–8.01 (m, 2H), 7.61 (d, J � 8.0 Hz, 2H), 7.55 (d, J �
2.7 Hz, 1H), 7.40–7.33 (m, 3H), 3.58 (q, J � 4.1 Hz, 4H),
3.29 (d, J � 3.3 Hz, 2H), 2.50 (d, J � 4.8 Hz, 4H); 13C NMR
(101 MHz, DMSO-d6) δ 168.98, 165.76, 164.84, 163.28,
157.88, 149.20, 139.86, 135.09, 131.70, 131.67, 130.89,
130.80, 129.41, 121.66, 120.40, 118.47, 115.91, 115.69,
108.77, 66.58, 60.80, 53.39; HRMS (m/z): calcd. For
C22H22FN4O3S (neutral M + H) 441.13966, found
441.14145.
3-fluoro-N-(3-(2-(2-morpholinoacetamido)thiazol-4-
yl)phenyl)benzamide 5h: White solid; yield, 74.8%; m.p.:
149.5°C–150.6°C; 1H NMR (400 MHz, DMSO-d6) δ 12.07
(s, 1H), 10.38 (d, J � 3.4 Hz, 1H), 8.40 (d, J � 3.0 Hz, 1H),
7.82–7.76 (m, 2H), 7.66–7.52 (m, 4H), 7.48–7.34 (m, 2H),
4.02 (s, 0H), 3.58 (d, J � 4.5 Hz, 4H), 3.29 (d, J � 3.5 Hz,
2H), 2.58–2.42 (m, 4H); 13C NMR (101 MHz, DMSO-d6)
δ 168.98, 164.54, 163.57, 161.14, 157.89, 149.16, 139.68,
137.58, 137.51, 135.11, 131.10, 131.02, 129.44, 124.35,
124.32, 121.82, 120.43, 119.08, 118.87, 118.50, 115.05,
1
p.: 137.0°C–139.5°C; H NMR (400 MHz, DMSO-d6) δ
12.22 (s, 1H), 9.79 (s, 1H), 8.27 (s, 1H), 7.56 (d, J � 7.7 Hz,
1H), 7.52 (d, J � 2.7 Hz, 1H), 7.49 (d, J � 8.0 Hz, 1H),
7.35–7.30 (m, 1H), 4.14 (d, J � 2.9 Hz, 2H), 3.98 (d, J �
2.9 Hz, 2H), 3.35 (d, J � 1.9 Hz, 11H); 13C NMR
(101 MHz, DMSO-d6) δ 169.04, 168.55, 157.75, 149.19,
139.21, 135.08, 129.42, 121.48, 119.78, 117.81, 108.80,
72.09, 70.86, 59.18, 59.09; HRMS (m/z): calcd. For
C18H23N4O4S (neutral
391.14766.
M + H) 391.14400, found
N-(3-(2-(2-morpholinoacetamido)thiazol-4-yl)phenyl)
cyclohexanecarboxamide 5m: White solid; yield, 69.1%;
m.p.: 165.5°C–166.8°C; 1H NMR (400 MHz, DMSO-d6)
δ 12.13 (s, 1H), 9.91 (s, 1H), 8.31 (d, J � 1.8 Hz, 1H),
7.55 (s, 1H), 7.44–7.41 (m, 1H), 7.33 (t, J � 7.9 Hz, 1H), 3.62
(t, J � 4.6 Hz, 4H), 3.33 (s, 2H), 2.54 (d, J � 4.5 Hz, 3H),
2.39–2.31 (m, 1H), 1.87–1.73 (m, 5H), 1.67 (d, J � 11.5 Hz,