(FAB) for C39H44N5O2Br ([M]+): calcd: 693.2678: found: 696.2766
(100%), 694.2731 (98%). Found C, 67.60; H, 6.22; N, 10.17. Calcd
C, 67.43; H, 6.38; N, 10.08%.
578.3129 (100%). Found C, 72.93; H, 6.67; N, 12.16. Calcd C,
72.76; H, 6.80; N, 12.12%.
Compound 13. Yellow oil, 68%. HPLC run time 26 min, Rt =
12.989 min. dH (500 MHz, MeOD) 8.16 (d, J = 8.71 Hz, 4H),
8.00 (s, 2H), 7.88 (d, J = 8.59 Hz, 2H), 7.77 (d, J = 8.71 Hz, 4H),
7.47 (d, J = 7.22 Hz, 2H), 7.39 (t, J = 7.56 Hz, 2H), 7.33 (d, J =
7.56 Hz, 1H), 7.19 (d, J = 8.82 Hz, 2H), 5.19 (s, 2H), 3.71 (m, 4H,
pyr), 3.30 (m, 4H), 3.12 (m, 4H, pyr), 2.62 (t, J = 6.76 Hz, 4H),
2.18 (m, 4H, pyr), 2.11 (m, 4H), 2.05 (m, 4H, pyr). dC (125 MHz,
MeOD) 173.88, 161.44, 157.70, 150.35, 138.43, 136.30, 131.88,
130.34, 129.53, 129.43, 128.92, 128.66, 128.58, 120.93, 116.47,
115.88, 70.97, 56.84, 54.93, 35.97, 25.66, 24.17. HRMS (FAB)
for C46H51N5O3 ([M]+): calcd: 721.3992: found: 722.4105 (100%).
Found C, 76.72; H, 7.06; N, 9.87. Calcd C, 76.53; H, 7.12; N,
9.70%.
Compound 3. Yellow oil, 56%. HPLC run time 20 min, Rt =
10.406 min. dH (500 MHz, MeOD) 8.15 (d, J = 8.71 Hz, 4H), 8.05
(s, 2H), 7.87 (d, J = 8.48 Hz, 2H), 7.79 (d, J = 8.71 Hz, 4H), 7.44 (d,
J = 8.48 Hz, 2H), 3.71 (m, 4H, pyr), 3.30 (m, 4H), 3.12 (m, 4H, pyr),
2.62 (t, J = 6.87 Hz, 4H), 2.56 (s, 3H, SCH3), 2.18 (m, 4H, pyr), 2.11
(m, 4H), 2.05 (m, 4H, pyr). dC (125 MHz, MeOD) 173.88, 161.41,
158.00, 150.64, 140.87, 136.16, 129.24, 128.61, 128.45, 127.45,
120.91, 116.59, 56.86, 54.94, 35.97, 25.67, 24.19, 15.28. HRMS
(FAB) for C40H47N5O2S ([M]+): calcd: 661.345: found: 662.3536
(100%). Found C, 72.57; H, 7.05; N, 10.78. Calcd C, 72.58; H,
7.16; N, 10.58%.
Compound 5. Yellow oil, 79%. HPLC run time 15 min, Rt =
10.162 min. dH (500 MHz, MeOD) 8.12 (d, J = 8.82 Hz, 4H),
8.10 (s, 2H), 7.90 (d, J = 8.59 Hz, 2H), 7.83 (d, J = 8.82 Hz,
4H), 7.44 (d, J = 8.59 Hz, 2H), 3.72 (m, 4H, pyr), 3.58 (t, J =
6.64 Hz, 4H), 3.16 (m, 4H, pyr), 2.97 (t, J = 6.64 Hz, 4H), 2.55 (s,
3H, SCH3), 2.18 (m, 4H, pyr), 2.06 (m, 4H, pyr). dC (125 MHz,
MeOD) 172.60, 158.07, 150.74, 141.84, 140.82, 136.27, 136.09,
128.66, 128.49, 127.50, 120.92, 116.67, 54.81, 52.88, 36.86, 24.33,
15.28. HRMS (FAB) for C38H43N5O2S ([M]+): calcd: 633.3137:
found: 634.3171 (100%). Found C, 72.14; H, 6.74; N, 11.19. Calcd
C, 72.01; H, 6.84; N, 11.05%.
Compound 14. Yellow oil, 81%. HPLC run time 26 min, Rt =
12.962 min. dH (500 MHz, MeOD) 8.17 (d, J = 8.71 Hz, 4H),
7.99 (s, 2H), 7.86 (d, J = 8.82 Hz, 2H), 7.79 (d, J = 8.59 Hz,
4H), 7.47 (d, J = 7.22 Hz, 2H), 7.39 (t, J = 7.22 Hz, 2H), 7.33
(d, J = 7.56 Hz, 1H), 7.18 (d, J = 8.82 Hz, 2H), 5.19 (s, 2H),
3.72 (m, 4H, pyr), 3.58 (t, J = 6.42 Hz, 4H), 3.18 (m, 4H, pyr),
2.96 (t, J = 6.42 Hz, 4H), 2.19 (m, 4H, pyr), 2.06 (m, 4H, pyr). dC
(125 MHz, MeOD) 172.58, 161.14, 158.01, 150.99, 140.81, 138.46,
136.38, 130.39, 129.55, 129.43, 128.93, 128.69, 128.59, 120.93,
116.67, 115.90, 70.99, 54.79, 52.86, 36.86, 24.31. HRMS (FAB)
for C44H47N5O3 ([M]+): calcd: 693.3679: found: 694.3781 (100%).
Found C, 76.31; H, 6.73; N, 10.20. Calcd C, 76.16; H, 6.83; N,
10.09%.
Compound 6. Yellow oil, 88%. HPLC run time 15 min, Rt =
8.191 min. dH (500 MHz, MeOD) 8.14 (d, J = 8.82 Hz, 4H), 8.03 (s,
2H), 7.93 (dd, J = 3.67 Hz, 1.03 Hz, 1H), 7.82 (d, J = 8.82 Hz, 4H),
7.68 (dd, J = 5.04 Hz, 1.03 Hz, 1H), 7.25 (dd, J = 5.04 Hz, 3.67 Hz,
1H), 3.73 (m, 4H, pyr), 3.58 (t, J = 6.53 Hz, 4H), 3.18 (m, 4H,
pyr), 2.96 (t, 6.53 Hz, 4H), 2.19 (m, 4H, pyr), 2.06 (m, 4H, pyr). dC
(125 MHz, MeOD) 172.70, 161.49, 158.43, 142.75, 141.01, 136.08,
129.64, 128.64, 128.31, 127.12, 121.00, 115.38, 54.83, 52.90, 36.87,
24.32. HRMS (FAB) for C35H39N5O2S ([M]+): calcd: 593.2824:
found: 594.2919 (100%). Found C, 70.86; H, 6.53; N, 11.90. Calcd
C, 70.80; H, 6.62; N, 11.79%.
Compound 16. Yellow oil, 95%. HPLC run time 15 min, Rt =
7.707 min. dH (500 MHz, MeOD) 8.18 (s, 2H), 8.07 (d, J = 8.82 Hz,
4H), 7.89 (d, J = 1.37 Hz, 1H), 7.85 (d, J = 8.82 Hz, 4H), 7.56 (d,
J = 3.44 Hz, 1H), 6.76 (dd, J = 3.44 Hz, 1.72 Hz, 1H), 3.71 (m, 4H,
pyr), 3.30 (m, 4H), 3.12 (m, 4H, pyr), 2.62 (t, J = 6.87 Hz, 4H),
2.19 (m, 4H, pyr), 2.11 (m, 4H), 2.04 (m, 4H, pyr). dC (125 MHz,
MeOD) 173.97, 161.46, 158.20, 153.05, 145.27, 141.01, 136.09,
128.56, 120.96, 116.16, 113.15, 110.29, 56.87, 54.96, 35.97, 25.70,
24.19. HRMS (FAB) for C37H43N5O3 ([M]+): calcd: 605.3366:
found: 606.3432 (100%). Found C, 73.57; H, 6.97; N, 11.64. Calcd
C, 73.36; H, 7.15; N, 11.56%.
Compound 7. Yellow oil, 83%. HPLC run time 15 min, Rt =
8.301 min. dH (500 MHz, MeOD) 8.13 (d, J = 8.82 Hz, 4H), 8.02
(s, 2H), 7.92 (dd, J = 3.67 Hz, 1.03 Hz, 1H), 7.79 (d, J = 8.71 Hz,
4H), 7.68 (dd, J = 5.15 Hz, 1.03 Hz, 1H), 7.25 (dd, J = 5.15 Hz,
3.67 Hz, 1H), 3.71 (m, 4H, pyr), 3.30 (m, 4H), 3.12 (m, 4H, pyr),
2.62 (t, 6.87 Hz, 4H), 2.18 (m, 4H, pyr), 2.11 (m, 4H), 2.04 (m,
4H, pyr). dC (125 MHz, MeOD) 174.01, 161.68, 158.45, 142.74,
141.00, 135.50, 129.64, 128.62, 128.31, 127.11, 120.99, 115.36,
56.88, 54.97, 35.98, 25.72, 24.20. HRMS (FAB) for C37H43N5O2S
([M]+): calcd: 621.3137: found: 622.3189 (100%). Found C, 71.52;
H, 7.04; N, 11.38. Calcd C, 71.47; H, 6.97; N, 11.26%.
Compound 17. Yellow oil, 83%. HPLC run time 18 min, Rt =
8.999 min. dH (500 MHz, MeOD) 8.19 (s, 2H), 8.06 (d, J = 8.71 Hz,
4H), 7.88 (d, J = 8.71 Hz, 4H), 7.63 (dd, J = 8.13 Hz, 2.06 Hz,
1H), 7.59 (d, 1.37 Hz, 1H), 7.07 (d, J = 8.25 Hz, 1H), 6.11 (s, 2H),
3.70 (m, 4H, pyr), 3.30 (m, 4H), 3.23 (m, 4H, pyr), 2.62 (t, J =
6.76 Hz, 4H), 2.18 (m, 4H, pyr), 2.11 (m, 4H), 2.05 (m, 4H, pyr).
dC (125 MHz, MeOD) 173.77, 161.40, 157.88, 150.96, 149.86,
140.90, 136.13, 133.78, 128.62, 122.26, 120.89, 116.73, 109.71,
108.31, 102.83, 56.80, 54.92, 35.90, 25.56, 24.18. HRMS (FAB)
for C40H45N5O4 ([M]+): calcd: 659.3472: found: 660.3549 (100%).
Found C, 72.67; H, 6.78; N, 10.71. Calcd C, 72.81; H, 6.87; N,
10.61%.
Compound 8. Yellow oil, 80%. HPLC run time 15 min, Rt =
7.102 min. dH (500 MHz, MeOD) 8.14 (s, 2H), 8.08 (d, J = 8.82 Hz,
4H), 7.85 (d, J = 8.71 Hz, 4H), 7.86 (m, 1H, furan), 7.51 (dd, J =
3.67 Hz, 0.46 Hz, 1H), 6.73 (dd, J = 3.55 Hz, 1.72 Hz, 1H), 3.73
(m, 4H, pyr), 3.58 (t, J = 6.53 Hz, 4H), 3.17 (m, 4H, pyr), 2.97 (t,
6.64 Hz, 4H), 2.18 (m, 4H, pyr), 2.06 (m, 4H, pyr). dC (125 MHz,
MeOD) 170.12, 161.79, 156.51, 151.73, 147.51, 142.14, 132.30,
129.74, 121.03, 116.50, 115.42, 114.19, 55.51, 52.15, 32.98, 24.03.
HRMS (FAB) for C35H39N5O3 ([M]+): calcd: 577.3053: found:
Compound 20. Yellow oil, 84%. HPLC run time 15 min, Rt =
9.018 min. dH (500 MHz, MeOD) 8.19 (d, J = 8.71 Hz, 4H), 7.92 (s,
2H), 7.77 (d, J = 8.71 Hz, 4H), 7.39 (m, 2H), 6.99 (d, J = 8.59 Hz,
1H), 6.05 (s, 2H), 3.72 (m, 4H, pyr), 3.58 (t, J = 6.64 Hz, 4H), 3.20
(m, 4H, pyr), 2.95 (t, J = 6.53 Hz, 4H), 2.18 (m, 4H, pyr), 2.07 (m,
This journal is
The Royal Society of Chemistry 2011
Org. Biomol. Chem., 2011, 9, 6154–6162 | 6159
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