August 2012
1043
ESI-MS m/z: 679.4 (M+H)+. IR (KBr) cm−1: 3430.6, 3306.4, (KBr) cm−1: 3451.3, 2846.4, 2223.7, 1557.1, 1514.0, 1346.1,
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2845.0, 1555.7, 1513.0, 1375.7, 1158.9, 778.3, 748.9. H-NMR 1159.1, 961.1, 778.0. H-NMR (300MHz, DMSO-d6) δ: 2.57
(300MHz, DMSO-d6) δ: 2.57 (4H, s), 2.90 (3H, s), 3.15 (4H, s), (4H, s), 2.89 (3H, s), 3.14 (4H, s), 4.10–3.65 (10H, m), 5.68
3.82 (6H, d, J=13.1Hz), 3.94 (4H, s), 5.53 (2H, s), 6.76 (1H, d, (2H, s), 6.96 (1H, s), 7.19–7.11 (3H, m), 7.47 (2H, s), 7.60 (1H,
J=6.7Hz), 7.36–7.08 (5H, m), 7.41 (1H, d, J=7.7Hz), 7.52 (1H, s), 7.76 (1H, s), 7.92 (1H, s), 8.26 (1H, s), 8.54 (1H, s), 10.55
d, J=7.5Hz), 7.72 (1H, s), 8.25 (1H, s), 8.52 (1H, d, J=6.9Hz), (1H, s). Anal. Calcd for C33H35N9O3S2(%): C, 59.17; H, 5.27; N,
10.53 (1H, s). Anal. Calcd for C32H35ClN8O3S2 (%): C, 56.58; 18.82. Found (%): C, 59.13; H, 5.29; N, 18.86.
H, 5.19; N, 16.50. Found (%): C, 56.52; H, 5.17; N, 16.55.
(E)-4-(2-(2-((1-Benzyl-1H-indol-3-yl)methylene)hydra-
(E)-4-(6-((4-(Methylsulfonyl)piperazin-1-yl)methyl)-2-(2- zinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-
((1-(4-(trifluoromethyl)benzyl)-1H-indol-3-yl)methylene)hydra- d]pyrimidin-4-yl)morpholine (13i): This compound was ob-
zinyl)thieno[3,2-d]pyrimidin-4-yl)morpholine (13d): This tained as off-white solid in 70% yield. mp 267–268°C. ESI-MS
compound was obtained as white solid in 72% yield. mp m/z: 645.6 (M+H)+. IR (KBr) cm−1: 3450.7, 2853.6, 1553.3,
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283–284°C. ESI-MS m/z: 713.1 (M+H)+. IR (KBr) cm−1: 1515.2, 1344.3, 1161.1, 777.7, 746.8. H-NMR (300MHz, DM-
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3447.1, 2853.1, 1554.1, 1515.3, 1327.9, 1161.9, 1118.9, 778.1. H- SO-d6) δ: 2.58 (4H, s), 2.90 (3H, s), 3.15 (4H, s), 3.79 (4H, s),
NMR (300MHz, DMSO-d6) δ: 2.58 (4H, s), 2.90 (3H, s), 3.15 3.85 (2H, s), 3.94 (4H, s), 5.43 (2H, s), 7.21 (8H, m), 7.48 (1H,
(4H, s), 3.80 (6H, s), 3.95 (4H, s), 5.56 (2H, s), 7.18–7.14 (3H, d, J=8.2Hz), 7.81 (1H, s), 8.26 (1H, s), 8.48 (1H, d, J=7.6Hz),
m), 7.60–7.50 (5H, m), 7.86 (1H, s), 8.27 (1H, s), 8.52 (1H, s), 10.52 (1H, s). Anal. Calcd for C32H36N8O3S2(%): C, 59.61; H,
10.53 (1H, s). Anal. Calcd for C33H35F3N8O3S2 (%): C, 55.60; 5.63; N, 17.38. Found (%): C, 59.56; H, 5.60; N, 17.45.
H, 4.95; N, 15.72. Found (%): C, 55.56; H, 4.94; N, 15.79.
(E)-4-(2-(2-((1-(2,3-Dichlorobenzyl)-1H-indol-3-yl)methyl-
(E)-3-((3-((2-(6-((4-(Methylsulfonyl)piperazin-1-yl)- ene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-
methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)hydrazono)- thieno[3,2-d]pyrimidin-4-yl)morpholine (13j): This compound
methyl)-1H-indol-1-yl)methyl)benzonitrile (13e): This com- was obtained as off-white solid in 76% yield. mp 287–288°C.
pound was obtained as light yellow solid in 74% yield. mp ESI-MS m/z: 713.6 (Cl=35), 715.6 (Cl=37) (M+H)+. IR
266–268°C. ESI-MS m/z: 670.4 (M+H)+. IR (KBr) cm−1: (KBr) cm−1: 3443.4, 1553.4, 1515.4, 1344.6, 1159.2, 960.8,
3429.8, 3310.3, 2845.1, 2229.0, 1558.2, 1513.4, 1157.9, 778.9. 777.4, 742.5. 1H-NMR (300MHz, DMSO-d6) δ: 2.58 (4H,
1H-NMR (300MHz, DMSO-d6) δ: 2.57 (4H, s), 2.90 (3H, s), s), 2.90 (3H, s), 3.15 (4H, s), 3.89–3.76 (6H, m), 3.95 (4H, s),
3.15 (4H, s), 3.80 (6H, s), 3.94 (4H, s), 5.50 (2H, s), 7.18–7.14 5.58 (2H, s), 6.60 (1H, d, J=7.7Hz), 7.35–7.03 (4H, m), 7.42
(3H, m), 7.53 (3H, s), 7.76 (2H, s), 7.85 (1H, s), 8.27 (1H, s), (1H, d, J=7.4Hz), 7.58 (1H, d, J=8.1Hz), 7.75 (1H, s), 8.26
8.51 (1H, s), 10.54 (1H, s). Anal. Calcd for C33H35N9O3S2 (%): (1H, s), 8.53 (1H, d, J=7.1Hz), 10.63 (1H, s). Anal. Calcd for
C, 59.17; H, 5.27; N, 18.82. Found (%): C, 59.14; H, 5.29; N, C32H34Cl2N8O3S2(%): C, 53.85; H, 4.80; N, 15.70. Found (%):
18.86.
(E)-4-(2-(2-((1-(3,4-Dichlorobenzyl)-1H-indol-3-yl)methyl-
C, 53.86; H, 4.82; N, 15.68.
(E)-4-(2-(2-((1-(2,6-Dichlorobenzyl)-1H-indol-3-yl)methyl-
ene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)- ene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-
thieno[3,2-d]pyrimidin-4-yl)morpholine (13f): This compound thieno[3,2-d]pyrimidin-4-yl)morpholine (13k): This compound
was obtained as white solid in 82% yield. mp 279–281°C. was obtained as off-white solid in 75% yield. mp 275–276°C.
ESI-MS m/z: 713.1 (M+H)+. IR (KBr) cm−1: 3438.0, 3296.5, ESI-MS m/z: 713.0 (Cl=35), 715.0 (Cl=37) (M+H)+. IR (KBr)
1556.4, 1515.9, 1344.7, 1159.3, 960.0, 778.4. 1H-NMR cm−1: 3423.2, 3006.0, 1628.0, 1549.0, 1198.3, 1158.2, 937.3,
(300MHz, DMSO-d6) δ: 2.57 (4H, s), 2.89 (3H, s), 3.15 (4H, 780.1. 1H-NMR (300MHz, DMSO-d6) δ: 2.57 (4H, s), 2.89
s), 4.05–3.66 (10H, m), 5.45 (2H, s), 7.36–7.07 (4H, m), 7.49 (3H, s), 3.15 (4H, s), 3.80 (4H, d, J=4.4Hz), 3.84 (2H, s), 3.93
(1H, d, J=8.0Hz), 7.69–7.53 (2H, m), 7.83 (1H, s), 8.27 (1H, (4H, s), 5.58 (2H, s), 7.36–6.95 (4H, m), 7.55–7.41 (1H, m),
s), 8.50 (1H, d, J=7.6Hz), 10.52 (1H, s). Anal. Calcd for 7.60 (3H, dd, J1=8.0Hz, J2=3.1Hz), 8.16 (1H, s), 8.49 (1H, d,
C32H34Cl2N8O3S2 (%): C, 53.85; H, 4.80; N, 15.70. Found (%): J=7.8Hz), 10.48 (1H, s). Anal. Calcd for C32H34Cl2N8O3S2 (%):
C, 53.84; H, 4.82; N, 15.69.
C, 53.85; H, 4.80; N, 15.70. Found (%): C, 53.80; H, 4.82; N,
(E)-4-(2-(2-((1-(2,4-Dichlorobenzyl)-1H-indol-3-yl)methyl- 15.75.
ene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-
(E)-4-(2-(2-((1-(3,4-Dichlorobenzyl)-1H-benzo[d]imida-
thieno[3,2-d]pyrimidin-4-yl)morpholine (13g): This compound zol-2-yl)methylene)hydrazinyl)-6-((4-(methylsulfonyl)pipera-
was obtained as white solid in 79% yield. mp 245–246°C. zin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine (15a):
ESI-MS m/z: 712.8 (Cl=35), 714.8 (Cl=37) (M+H)+. IR (KBr) This compound was obtained as white solid in 76% yield.
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cm−1: 3438.5, 1553.9, 1515.8, 1344.7, 1159.3, 960.0, 777.4. H- ESI-MS m/z: 713.1 (Cl=35), 715.1 (Cl=37) (M+H)+. H-NMR
NMR (300MHz, DMSO-d6) δ: 2.54 (4H, s), 2.86 (3H, s), 3.11 (300MHz, DMSO-d6) δ: 2.57 (4H, s), 2.90 (3H, s), 3.14 (4H, s),
(4H, s), 3.76 (4H, s), 3.81 (2H, s), 3.91 (4H, s), 5.48 (2H, s), 6.72 3.62 (4H, s), 3.73 (4H, s), 3.86 (2H, s), 6.14 (2H, s), 7.15 (1H,
(1H, d, J=8.3Hz), 7.07 (1H, s), 7.23–7.09 (2H, m), 7.31 (1H, d, s), 7.27 (3H, d, J=6.8Hz), 7.55 (2H, d, J=8.9Hz), 7.66 (1H, d,
J=8.4Hz), 7.37 (1H, d, J=7.8Hz), 7.67 (2H, d, J=5.4Hz), 8.21 J=6.8Hz), 7.89 (1H, s), 8.26 (1H, s), 11.41 (1H, s). Anal. Calcd
(1H, s), 8.48 (1H, d, J=7.6Hz), 10.47 (1H, s). Anal. Calcd for for C31H33Cl2N9O3S2 (%): C, 52.10; H, 4.65; N, 17.64. Found
C32H34Cl2N8O3S2 (%): C, 53.85; H, 4.80; N, 15.70. Found (%): (%): C, 52.06; H, 4.63; N, 17.69.
C, 53.80; H, 4.82; N, 15.76.
(E)-4-(2-(2-((1-(4-tert-Butylbenzyl)-1H-benzo[d]imidazol-2-
(E)-3-((3-((2-(6-((4-(Methylsulfonyl)piperazin-1-yl)- yl)methylene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-
methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)hydrazono)- yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine (15b): This
methyl)-1H-indol-1-yl)methyl)benzonitrile (13h): This com- compound was obtained as off-white solid in 78% yield. mp
pound was obtained as white solid in 82% yield. mp 252–254°C. ESI-MS m/z: 702.4 (M+H)+. IR (KBr) cm−1:
264–265°C. ESI-MS m/z: 670.2 (M+H)+, 692.1 (M+Na)+. IR 3437.1, 1553.7, 1516.9, 1345.9, 1159.9, 777.9, 743.9. 1H-NMR