8.08(s, 1H), 7.90(d, J ) 8.0 Hz, 2H), 7.55–7.43(m, 5H), 7.20(d,
J ) 8.8 Hz, 1H), 3.52(s, 2H), 2.34(bs, 8H), 2.22(s, 3H), 2.15(s,
3H); 13C NMR (CDCl3) δ 173.8, 165.4, 162.7, 159.0, 151.5,
148.5, 142.5, 137.8, 136.5, 134.9, 133.8, 132.7, 130.8, 129.3,
126.9, 124.1, 123.8, 124.0, 115.2, 112.9, 108.4, 62.5, 55.1, 53.1,
46.0, 17.7; Anal. Calcd for C29H31N7O: C, 70.55; H, 6.33; N,
19.87. Found: C, 70.13; H, 6.20; N, 19.32.
N-(4-Methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phe-
nyl)-4-(piperidin-1-ylmethyl)benzamide (1a): mp 197–200
°C; 13C NMR (CDCl3) δ 173.8, 165.5, 160.5, 159.0, 148.5,
147.4, 142.6, 137.8, 136.6, 135.0, 133.8, 132.6, 130.8, 129.5,
127.0, 124.1, 123.8, 115.3, 112.9, 108.4, 63.2, 54.5, 25.8, 17.7;
Anal. Calcd for C29H30N6O: C, 72.77; H, 6.32; N, 17.57. Found:
C, 72.46; H, 6.10; N, 17.35.
N-(4-Methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phe-
nyl)-4-(morpholinomethyl)benzamide (1b): mp 210–212 °C;
13C NMR (CDCl3) δ 173.8, 165.4, 162.7, 160.5, 159.0, 151.5,
148.5, 137.7, 136.6, 134.9, 134.0, 132.6, 130.8, 129.3, 127.1,
124.2, 123.7, 115.3, 113.0, 108.3,66.9, 62.9, 53.6, 17.7; Anal.
Calcd for C28H28N6O2: C, 69.97; H, 5.88; N, 17.50. Found: C,
69.71; H, 5.65; N, 17.25.
4-((1H-Imidazol-1-yl)methyl)-N-(4-methyl-3-(4-(pyridin-
3-yl)pyrimidin-2-ylamino)phenyl)benzamide (1c): mp 200–203
°C; 13C NMR (CDCl3) δ 172.8, 163.1, 160.9, 155.7, 150.2,
148.6, 142.1, 138.9, 136.0, 134.7, 133.7, 133.1, 131.0, 130.5,
129.0, 128.4, 127.6, 125.3, 124.5, 120.5, 110.9, 102.8, 54.1,
17.2; Anal. Calcd for C27H23N7O: C, 70.25; H, 5.03; N, 21.25.
Found: C, 69.99; H, 5.15; N, 21.01.
C29H29N5O2: C, 72.62; H, 6.09; N, 14.61. Found: C, 72.46; H,
5.89; N, 14.29.
N-(4-Methyl-3-(4-(pyridin-2-yl)pyrimidin-2-ylamino)phe-
nyl)-4-((4-methylpiperazin-1-yl)methyl) benzamide (1f): mp
159–161 °C; 13C NMR (CDCl3) δ 173.5, 163.4, 162.9, 161.0,
155.1, 149.3, 142.5, 138.7, 137.0, 134.2, 132.6, 130.5, 129.3,
126.8, 124.7, 124.1, 120.4, 110.8, 107.4, 61.5, 55.6, 53.1, 44.5,
17.7; Anal. Calcd for C29H31N7O: C, 70.55; H, 6.33; N, 19.87.
Found: C, 70.23; H, 6.42; N, 19.08.
N-(4-Methyl-3-(4-(pyrazin-2-yl)pyrimidin-2-ylamino)phe-
nyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide(1g). mp
195–197 °C; 13C NMR (CDCl3) δ 172.7, 164.2, 163.4, 159.1,
145.9, 144.2, 143.8, 142.0, 141.5, 138.7, 133.6, 132.3, 130.0,
128.7, 126.9, 124.3, 112.1, 61.8, 55.0, 52.9, 45.7, 17.8; Anal.
Calcd for C28H30N8O: C, 67.98; H, 6.12; N, 22.66. Found: C,
67.57; H, 6.19; N, 22.13.
N-(3-(4-(Furan-2-yl)pyrimidin-2-ylamino)-4-methylphe-
nyl)-4-((4-methylpiperazin-1-yl)methyl) benzamide (1h): mp
170–172 °C; 13C NMR (CDCl3) δ 168.1, 158.4, 156.3, 151.8,
144.8, 142.3, 137.9, 136.5, 133.9, 130.7, 129.2, 127.0, 123.9,
112.8, 112.5, 106.6, 54.9, 52.9, 45.9, 17.7; Anal. Calcd for
C28H30N6O2: C, 69.67; H, 6.27; N, 17.42. Found: C, 69.85; H,
6.04; N, 17.11.
N-(4-Methyl-3-(4-(thiophen-2-yl)pyrimidin-2-ylamino)phe-
nyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide (1i): mp
186–188 °C; 13C NMR (CDCl3) δ 172.3, 163.6, 159.9, 157.0,
141.8, 140.0, 138.7, 133.2, 132.0, 130.1, 129.3, 127.5, 127.3,
127.0, 124.9, 123.8, 111.5, 108.2, 104.7, 62.3, 54.4, 52.7, 42.9,
17.6; Anal. Calcd for C28H30N6OS: C, 52.32; H, 4.71; N, 13.08.
Found: C, 52.48; H, 4.51; N, 13.16.
N-(4-Methyl-3-(4-phenylpyrimidin-2-ylamino)phenyl)-4-
(piperidin-1-ylmethyl)benzamide (1d): mp 202–207 °C; 13
C
NMR (CDCl3) δ 173.7, 165.4, 160.4, 158.5, 138.0, 137.0, 136.5,
133.7, 130.8, 129.4, 129.0, 128.8, 127.2, 126.9, 123.8, 116.9,
115.0, 112.6, 108.6., 63.3, 54.5, 25.9, 17.7; Anal. Calcd for
C30H31N5O: C, 75.43; H, 6.55; N, 14.67. Found: C, 75.20; H,
6.38; N, 14.49.
N-(4-Methyl-3-(4-phenylpyrimidin-2-ylamino)phenyl)-4-
(morpholinomethyl)benzamide (1e): mp 200–206 °C; 13C
NMR (CDCl3) δ 174.1, 163.7, 161.0, 158.9, 142.1, 139.0, 133.5,
133.0, 132.4, 130.2, 129.7, 129.1, 127.9, 127.6, 127.1, 124.3,
111.8, 107.4, 104.8, 67.2, 59.9, 54.4, 17.6; Anal. Calcd for
Acknowledgment
Financial support was provided by the Nature Science
Foundation of ShaanXi Province, China (03JC01), and Scientific
Technology Foundation of Educational Committee of ShaanXi
Province, China (2003k08-G5).
Received for review November 23, 2007.
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